TLIAW: Nor the Battle to the Strong

I returned, and saw under the sun,
That the race is not to the swift nor the battle to the strong
…but time and chance happeneth to them all.


—Ecclesiastes 9:11

Nor the Battle to the Strong: The Atlantic’s ‘Rising Stars’ in Retrospect

All Blank Covers Together (Shrunk) (1).png


One post each day at 9:45 AM Eastern Standard Time, beginning Monday, January 29. Inspired by this article, and by @Callan's Presidential.​
 
Last edited:
Introduction
September 20, 2024

How do you predict the future?

It’s a tough question, and God only knows how many people have made fools of themselves trying to answer it. I, perhaps unfortunately, am one of them.

Twenty-five years ago, as a young cub reporter with The Atlantic’s political desk, I was given a prized assignment: look across the country—dig into state legislatures, trawl through city councils, roam the halls of Congress—and identify the rising stars who would dominate American politics in the 21st century. I went about my work with the arrogant diligence one might expect of an Ivy League graduate, and my efforts soon bore fruit. Once a year from 1999 to 2004, splayed across the cover of our monthly print edition was an unfamiliar face, one our readers were told would soon rise to the peaks of glory and walk among kings and emperors.

Sadly, Keith Ellison did not make the list. When I started my search, he was busy coaching high school track in Minneapolis. Neither did Lanhee Chen, who was twenty-one years old and working on the first of his many Harvard degrees. Lisa Fairfax was teaching case law at the University of Maryland, while Tagg Romney was head of marketing for the Los Angeles Dodgers. Most of today’s superstars were flying far, far below the radar. In their stead, I picked six promising politicians, almost all of whom, as it turned out, were destined for failure. By the time “Rising Stars” was canceled in 2004, all but one had lost their careers to scandal, poor timing, or just plain bad luck. The series is now infamous as an example of how pigheadedly wrong a journalist can be, while “The Atlantic Curse” has infiltrated our lexicon as a term for early success portending eventual failure (although it still reminds me more of Captain Kidd than Meg Whitman).

A quarter of a century has passed since my first profile appeared in print. In that time, America and its politics have changed so dramatically that to read through it now is to travel back to a bygone age, to a time when a hopeful generation looked out over a new millennium and saw endless possibilities stretching out before it. A time when the future seemed to belong to bridge-builders and not to ideological crusaders, and when the American people seemed well and truly fed up with partisan gridlock. Today, this might feel incredibly naïve, but for those of us who came of age within a decade of the fall of international communism, it was a challenge, an exhortation to grab the world by the horns and wrestle it into something worth believing in.

That striving, hopeful optimism has died a thousand deaths. Its obituaries have ranged from the mournful to the joyful (the late Senator Alan K. Simpson misted many an eye three years ago when he begged for peace and civility in his remarks to the National Press Club, but he was so viciously mocked online that any politician who takes that tone now risks being branded a “Simp”). In its absence, election season has become an unbearably nasty time. Politicians pelt each other with insults, bald-faced lies rage across the internet like tropical diseases, and public discourse sinks to a level that makes Jerry Springer look like Shakespeare. By the end, the people are thoroughly disgusted with all things political. The Onion sold three million copies of its 2008 election day special (the one with the banner headline “AMERICA CONCEDES DEFEAT”), while The Sam Reich Hour attracted attention in 2020 for the long list of nicknames it gave that year’s presidential race (my personal favorites include “Lice on Rats on a Horse Corpse on Fire” and “America’s Sucktastic Cirque de Dismay”).

This election has felt a bit tamer than the last few. While the contest has been far from chivalrous, President McInnis has mostly managed not to mudsling, while the Morgan campaign has won plaudits for its hopeful, optimistic bent. Some warned of backlash last month when Democrats nominated America’s first openly gay vice-presidential candidate, but reactions on the right have been surprisingly muted, with little more than the typical pearl-clutching over values and morality. Still, to Americans of a certain age, the all-consuming negativity hangs over our memories like a dark, sulfuric cloud. To paraphrase a fellow old geezer, “now there’s a wall between us, something there’s been lost. We took too much for granted, we got our signals crossed.”

At my editor’s behest, I’ll be rounding out this election year with a where-are-they-now series on my former stars. To that end, I’ll be spending the next six weeks criss-crossing the country in a long, circuitous route, visiting each of them in their homes from the concrete forests of Newark to the viny hills of Napa. None of them have ended up where they thought they would: the man who once seemed destined to be his city’s next mayor ended up running a civic center, the former U.S. senator now spends his free time oil painting, and the software analyst who once claimed few ambitions beyond a seat on the city council has reached dizzying new heights and broken barriers that seemed impenetrable just a few short years ago. Their paths have defied prediction, but they have no regrets. The prizes they sought are (mostly) out of reach, but where ambition has failed them, they have found satisfaction in the tiny joys of life.

This trip has allowed me to reflect on a great many things—how our idea of success favors fancy titles over self-realization, how the most powerful men and women of our time were all once ordinary Joes and Janes—but above all, it has affirmed to me that luck, not talent or skill, is the ultimate arbiter of fate. As the scripture says, “the race is not to the swift nor the battle to the strong, but time and chance happeneth to them all.”

A new profile will be published every Friday from now until election day. For your amusement, the original “Rising Stars” series can be found here.
 
God this is so cool. It's already gotten me hyped for some grim tidings and no mistake!
 
1999
September 27, 2024

Chicago’s Hyde Park Boulevard is the picture of American bliss. It charts a wide, straight path from the slender beaches of Lake Michigan to the verdant beauty of Washington Park, flanked on either side by elegant, three-story homes that mix the measured aesthetics of ‘50s suburbia with the stately grandeur of 19th-century Newport. These houses stand just a few blocks away from the University of Chicago, where many of the residents are tenured faculty. The one at which I arrive on a balmy, mid-July evening is as stolid as the rest, with one striking distinction: a basketball hoop at the end of the driveway. The owner of that hoop lures me into a head-to-head matchup, assuring me with a fatherly chuckle that he’s long past his prime. But, as I remember after giving up four layups in thirty seconds, in his prime, he was pretty damn good.

Barack Obama may truly have it all: a loving family, a beautiful home, and an illustrious career flush with accolades and accomplishments. But his life hasn’t always been so charmed. He was born in Hawaii in 1961 to a Kansan mom and a Kenyan dad who divorced before his third birthday. For much of his childhood, he was geographically estranged from both parents; his namesake father moved back to Kenya and later died in a car crash, while his mother was an academic whose work led her to spend years at a time in rural Indonesia. Aside from a few youthful years with his mom in Jakarta, Barack was raised mostly by his grandparents in Honolulu. Though he did well in school, he also abused drugs and skipped class, behavior which, he now recognizes, stemmed from anger at his lack of a firm father figure, “even though I didn’t necessarily realize it at the time.”

By college, however, Barack had pulled himself together. In 1983, he graduated from Columbia University and soon moved on to Harvard, where he became the first black president of the Harvard Law Review and met his wife Michelle while interning at a prestigious firm. After graduating in 1991, the couple settled down in the Windy City, where Barack took up a position as a lecturer at the University of Chicago. Within five years, he had established himself as a premier citizen of Hyde Park, and in 1996 he sought and won a seat in the Illinois Senate.

It was here that he first came to my attention. By the time we first met in January of 1999, Barack had accomplished more in two years than most Illinois politicians do in twenty. In his first term, he helped pass laws that banned many underhanded lobbying techniques, modernized the state’s bloated welfare system, delivered tax credits and childcare to low-income families, and compelled factories to warn workers when layoffs were imminent. That would have been a formidable sheet of accomplishments for any legislator, but for a freshman senator of the minority party, it was stunning.

If his record was impressive, he had the personality to match. Tall, handsome, warm and prodigiously charismatic, Barack possessed a rich, baritone voice that he wielded to powerful effect on the Senate floor, often winning over dithering colleagues on the strength of his arguments alone. In our interview at a Kenwood café, I asked whether he was considering a run for higher office. With a coy, politician’s wink, Barack assured me that the only things on his mind were his students, his constituents, and his newborn daughter, Malia. But even then, it was clear that his heart was set on higher glories.

Within a year, he would make his move. In 1999, South Side Congressman Bobby Rush ran for Mayor of Chicago and lost miserably. Barack, who lived in Rush’s district, sensed an opportunity to challenge the Representative for his seat in Congress. Barack’s mentors advised against it, warning that he would struggle to dislodge an incumbent, but he pressed ahead, declaring his candidacy in early 2000.

This, he admits after we head inside for dinner, was hubris, much of it driven by the attention he received following his profile in The Atlantic. For months after his story was printed, Barack says, “every news magazine in the Midwest was calling my office to beg for interviews. I had people from Arkansas and New Hampshire sending me letters, asking me to move there and run for Governor. It was all pretty overwhelming.” Michelle agrees, adding with cheerful bluntness that by the time Barack kicked off his congressional campaign, “he thought he was a much better politician than he actually was.”

As the race unfolded, Barack’s confidence crumbled. It was his first competitive election (he’d won both of his state Senate races unopposed), and he soon discovered how much easier it is to hold office in Chicago than to win it. While Barack struggled to find a convincing line of attack, Rush lambasted him as an “elitist fool” who had “read about the civil rights marches and thought he knew all about it.” Whereas Rush had deep ties to the district and its black community, Barack had lived there less than a decade and had little cachet beyond white, affluent Hyde Park. In one particularly stinging rebuke, another opponent, Donne Trotter, called him “the South Side’s white man in blackface”.

In the end, Barack says, “I got my ass kicked.” The following year brought happier news as Michelle gave birth to fraternal twins, Tasha and Dante. But things took a turn for the worse when it was discovered that Tasha had a congenital heart defect that threatened to kill her before the age of six. Stung by his loss to Rush and needing more time to care for his daughter, Barack chose not to run for re-election to the state Senate in 2002. His term expired the following year, although he was almost as productive in his last two years as in his first two, sponsoring legislation to combat racial profiling and expand access to health care.

The next few years were a tough time for the Obamas. Before her third birthday, Tasha would undergo twenty-seven separate surgical procedures, racking up mountains of medical debt. To supplement their income from the University, both Barack and Michelle became associates at the law firm Sidley Austin, working long into the night on cases and briefs. Michelle’s mother Marian would often step in to look after the kids, and for a year and a half, the family lived in a one-bedroom apartment to save on rent. “It was a tough time,” Michelle recalls with a loving look over at her husband, “but it brought us so much closer than we’d ever been before”. For her and Barack, the experience of working alongside one another deepened their sense of mutual respect and strengthened their marital bond. “That Sun Microsystems acquisition probably saved our marriage,” Barack suggests, only half-joking.

Eventually, the clouds began to lift. After three harrowing years, Tasha’s condition finally improved, and the medical bills thinned out. Barack’s academic career also began to take off—in 2005, he became a full professor and resigned from Sidley Austin (where Michelle is now a partner). By the time Tasha underwent her very last heart operation at the age of ten, Barack was a tenured professor well regarded by his students and peers, and he’d written a book on the Commerce Clause that was lauded by constitutional scholars.

Although his own bout with public office was over, Barack hadn’t lost his progressive sensibilities or his ever-present interest in politics. In 2008, he once again rose to the spotlight as a leader in the fight for marriage equality in Illinois. When the General Assembly voted to ban gay marriage through an amendment to the state constitution, Barack co-founded the grassroots federation Prairie State Love, which mobilized millions of voters to strike down the amendment at referendum. When Republican Governor Jim Oberweis responded with an executive order that banned county clerks from certifying same-sex marriages, Barack fought back with a lawsuit, arguing that the order violated due process, checks and balances, and basic human rights. The courts concurred, and in 2009, the order was overturned. Elements of Barack’s argument would later be folded into Schlansky v. Barletta, the landmark U.S. Supreme Court ruling which legalized same-sex marriage nationwide in 2011.

If “Rising Stars” boosted Barack’s profile, the marriage fight launched him into the stratosphere. In the years since, he tells me over a plate of Michelle’s delectable penne alla vodka, he’s been scouted for every conceivable office: Mayor of Chicago, Illinois Attorney General, even the House seat he once lost to Bobby Rush. During the governor’s race in 2010, then-candidate Lisa Madigan offered him a spot as her running mate, and when U.S. Senator Jack Ryan resigned from office in 2012, rumor had it she was courting Barack as his replacement. Each time, Barack declined. “When I was younger,” he reflects, “I got caught up in the glory of politics. It made me lose sight of what’s really important.” He has no regrets about his time in office, he says, but Tasha’s illness helped him realize that no amount of power or prestige will ever matter more to him than the well-being of his family.

It also helped him discover a hidden love of teaching. The lecturing job was never supposed to be much more than a bridge to bigger and better things, but as the bills piled up and Barack’s days were hemmed in by grueling work at Sidley and tense nights at the Lincoln Park Health Center, teaching became his refuge from the world. For a few hours each week, he could set aside the anxieties of life to guide a new generation of students through the foundations of American constitutional law. The same traits that made him an effective legislator make him a fantastic professor, and while he’s had less time to teach since becoming an associate dean in 2015, his seminars on Effective Altruism and Civil Rights in the 21st Century have waitlists stretching into the hundreds.

Professor O (as he is known in the classroom) is loved not only for his mastery of the law but also for his sense of humor. A few years ago, to inspire his students to study for their midterms, Barack sent out a clip of himself singing along to Donnie McClurkin’s 2003 hit “Yes You Can”. The video became a schoolwide sensation, and now, whenever exam season rolls around, every bulletin board in the Law School is plastered with stylized images of his face undergirded by the caption “YES YOU CAN”.

Though he treasures his job for the minds it’s allowed him to touch, Barack’s pride and joy will always be his children. “My one determination in life,” he says, “is to be the kind of dad my father never was.” Grinning wide, he tells me that in twenty-six years of parenting, he can count on one hand the number of times he’s missed a football game, chess tournament, or piano recital. He invites me into the living room, where every wall is covered with photos of the Obama brood camping out at the Indiana Dunes, sucking down strawberry milkshakes, or just enjoying one another’s company with broad, beaming smiles. It’s the kind of picture-perfect childhood Barack can only wish he had, and he’ll happily concede that he derives a vicarious sense of joy from providing it to his kids. “I didn’t have a lot of these things growing up,” he says, “so if I can break the cycle, to me, that means a lot.”

Already, the Obama kids are on track to surpass their parents’ record of greatness. Malia got her master’s degree from Johns Hopkins last year and is now a research fellow at the Lieberman Foundation, one of Washington’s foremost foreign policy think tanks. Tasha is about to start her second year at Georgetown Law, where she hopes to follow in her parents’ footsteps. Dante, meanwhile, went to the University of Michigan on a football scholarship, and this past April, he was drafted as a tight end by the San Antonio Raiders. Though Barack is immensely proud of his children, the longtime Bears fan admits that it’s been tough switching his allegiance to a new team. When Jordan Ta’amu, the Packers’ star quarterback, announced in June that he’d be ditching Green Bay for Denver, Barack couldn’t bring himself to celebrate, knowing that the move would only strengthen one of Dante’s division rivals in the AFC West.

With the kids out of the house, Barack has a lot more time than he used to for civic engagement and volunteering. In 2021, Barack joined the executive board of the Austin Knights, a grassroots advocacy group on Chicago’s West Side. In March, he became one of the Morgan campaign’s co-chairs in Illinois, and in the very likely event Morgan carries the state in November, Barack is slated to serve as a presidential elector. Though his hair has started to gray, Barack refuses to even consider slowing down; retirement is beyond countenance. Still, he remains adamant that no worldly thing will ever come between him and his family. “This house, the law, my career,” Barack reflects, “I’m proud of it all, but Michelle and the kids mean absolutely everything to me. And I’d give it all up in a heartbeat to keep them safe.”

The midsummer sky has grown dark. Barack and Michelle beg me to stay for dessert, but I’ve got an early flight tomorrow and need my sleep. The Obamas wave goodbye as I climb back into my rental car, pull away from the curb, and set off into the night. Just as the house disappears behind a corner, I steal one last glimpse into the rearview mirror. There they are, standing on the doorstep, smiling into each other’s eyes like a pair of newlyweds. After thirty-two years of marriage, they’ve held on to the kind of starstruck, loverly passion some couples lose in the first month. I can’t think of any office, high or low, that’s worth as much as that.

1999 Obama Framed NTB (1).png
 
Oh I love this concept very interesting to explore famous figures from our world just living normal lives
 
2000
October 4, 2024

When I was a kid, I watched a lot of TV. One day, I was sitting at home flipping through the channels when I chanced upon a poofy-haired old man with a palette and a paintbrush. I watched, mesmerized, as the man transformed an empty canvas into a gorgeous mountain view, narrating each stroke of the brush in a soft, velvety voice. Years later, I would discover that he was an Air Force veteran who filmed ten seasons of an art show for PBS before dying of cancer in 1995. I’ve met other people who remember the man, but none of them are under the age of 40, and I’ve never encountered anyone else who can make painting feel so simple and serene—until, that is, I caught up with my second star.

The address he gives me is that of a lakeside estate nestled deep into the South Carolina Lowcountry. The drive down from Charleston is a long one, and at his request, I set off early in the morning, before the sun is in the sky. The manicured, suburban streets lined with “VOTE McINNIS” signs soon give way to two-lane highways and then to gravel country roads, winding deeper and deeper into the marshes until my Nokia loses its signal. By the time I pull into the dirt driveway, a few rays of pink are peeking out over the horizon. I walk up to the front door and raise my hand to knock, only to spot my host a few hundred yards off to the side, facing east with a stool and an easel.

I approach. “Morning,” he says, grinning softly, then stretches a blank canvas and starts painting in the sunrise. I watch him mix his pigments in complete and utter serenity, struggling to remind myself that this man was once at the center of one of Washington’s bloodiest political proxy wars.

Lindsey Graham never aspired to be an artist. Where he grew up, boys like him rarely aspired to much of anything. He was born and raised in Central, South Carolina, a tiny textile town buried deep into the state’s mountainous northwest. He was not a model student; when he told his civics class that he wanted to become governor one day, they burst out laughing. Still, Lindsey knew he wanted more out of life than his town had to offer. In 1973, he enrolled at the University of South Carolina and set his sights on a legal career. Then, at the age of eighteen, he was struck by the most terrible kind of tragedy: both his parents died within two years of each other, orphaning both him and his younger sister Darline. Lindsey thought about dropping out, but Darline wouldn’t hear of it, so he pressed on through three years of law school, driving home on the weekends to care for his sister. After graduation, he served four years in the Air Force, traveling to exotic places like Istanbul and Madrid, before leaving in 1989 to practice family law in the little town of Seneca.

Soon afterward, ambition bit him. “I was never particularly political growing up,” Lindsey recalls, mixing a gob of alizarin crimson with titanium white, “but even when I was young, I always had a notion that I might get into politics one day.” In 1992, he ran for the state house and won, becoming the first Republican ever to win an election in his district. Two years later, longtime Congressman Butler Derrick announced his retirement, leaving the seat open for the first time in decades. Lindsey leapt into the race and romped to an easy win, one of dozens of young-blood conservatives elected to Congress that year in what later became known as the Republican Revolution.

Lindsey soon distinguished himself from the rest of his rowdy freshman class. He was as conservative as they came, pushing for big tax breaks and sharp cuts to the federal deficit. But he also displayed a keen eye for compromise, joining with Democrats to reform Medicare and open new doors of opportunity for blue-collar workers. As a prosecutor in Bill Clinton’s impeachment trial, Lindsey shocked observers by chiding his own party when it went too far, and his aw-shucks demeanor made him a natural on cable TV. By the late ‘90s, it was clear that Lindsey’s star was on the rise, and he knew exactly where his ambitions were leading him: longtime U.S. Senator Strom Thurmond, who had represented South Carolina for almost half a century, would be retiring in 2002. Lindsey made no secret of his plans to run, raising boatloads of cash and freezing out potential competitors. “The job doesn’t come open very often,” he quipped in his smooth, Southern drawl, “and when the train leaves the station, it don’t come back in our lifetime.”

By the time Lindsey and I finally met at a Greenville diner in early 2000, he was fully immersed in an electoral campaign—not his own, but that of Arizona Senator John McCain, who was mounting a longshot bid for the presidency. Lindsey had become McCain’s biggest fan in South Carolina, barnstorming up and down the state lobbing attacks at Republican frontrunner George W. Bush. When I asked whether this might come back to haunt him if McCain lost, Lindsey brushed me off. “I’ve got the secret to political success,” he claimed wryly: “lucky timing.”

Indeed, the following few years would bring a long string of victories one might fairly ascribe not just to luck but to genuine, political skill. McCain lost the nomination, but Lindsey easily won a fourth term in Congress. When the Senate seat opened up as expected, he faced a challenge from fellow Republican Mike Fair, who charged that Lindsey’s attacks had weakened Governor Bush and helped cost Republicans the White House. But Lindsey dipped into his massive war chest and fended Fair off by a comfortable margin. The election itself was a challenge—the War in Afghanistan was going well, Bin Laden was dead in the hills of Tora Bora, and President Gore was so popular that many Democrats thought they could flip the seat on his coattails alone. But Lindsey’s campaign was efficient and professional. While Republicans lost next door in Georgia and North Carolina, Lindsey pulled off a close win and returned to Washington in triumph, the Palmetto State’s first new senator in 38 years.

The early months of his term were idyllic. Senator McCain took Lindsey under his wing, helping him secure plum committee assignments. When U.S. forces invaded Iraq, Lindsey quickly became one of the Senate’s loudest hawks, appearing frequently on CNN to speak in support of the invasion. Through McCain, Lindsey also got to know Vice President Joe Lieberman, giving him the kind of White House ties most first-term senators can only dream of.

But not everyone liked Lindsey. Some Republicans thought he was a sanctimonious schmuck whose lust for the spotlight made him an easy mark for scheming liberals. Lindsey openly disdained the swell of hardline, Christian nationalism that had taken root in the GOP, and soon, he was a figure of hate for the Religious Right. Sam Brownback kicked off his presidential run in 2003 with a speech denouncing Lindsey as a fellow traveler to the conservative cause; never one to hold his tongue, Lindsey fired back, claiming to have accomplished more in one year than Brownback had in seven. When Brownback won the nomination, Lindsey gave only the most tepid of endorsements, and when Al Gore won a second term, he felt utterly vindicated. Asked to explain the loss during an interview on MSNBC, Lindsey said “people are smart. They can tell when they’re being conned.”

“After that," Lindsey admits, loading his brush with Prussian blue, “I guess you could say I got a little biggity.” He fancied himself the future of the Republican Party, and even pondered a presidential run of his own. But he failed to see how far out of step he was with the GOP base. He declined to sign Jerry Falwell’s Family Values Pledge, even though more than two-thirds of Republican voters supported it. In 2006, when Alabama Congressman Roy Moore proposed that the Ten Commandments be displayed in federal courtrooms, Lindsey enraged evangelicals by calling the idea “absolute, total trash.” Later that year, when Minnesota Senator Paul Wellstone introduced a bill to permit gay men and women to serve openly in the military, the most basic political instincts would have told Lindsey to steer clear. Yet, when pressed by reporters, he said “I guess I’ll have to think about it.”

But the last straw? “I’d say it was the Garland vote.”

In February 2007, Chief Justice William Rehnquist died of cancer, leaving the Supreme Court evenly split between liberals and conservatives. The hunt began for Rehnquist’s successor, and to Republicans, the stakes couldn’t have been higher: the ideological balance of the Court was at stake, and with it the dreams of an entire generation of conservatives. Republicans knew they weren’t going to get another crusading Chief Justice, but with 52 seats in the Senate plus one friendly independent, they at least felt confident they could check President Gore’s worst excesses. But then, Gore tossed out the Republican-approved shortlist and nominated Merrick Garland, an unacceptably liberal judge on the D.C. Court of Appeals. Majority Leader Trent Lott made it abundantly clear that Garland would not be confirmed, yet the White House pressed ahead with so much steam that Lott decided to stage a floor vote just to take them down a peg or two.

To this day, Lindsey insists he never saw it coming. It was supposed to be nothing more than a piece of political theater. When he walked into the Senate chamber that night, he knew he’d be voting to confirm, but he’d cleared it in advance with GOP leadership—they’d needed a “yes” vote on the Judiciary Committee to advance Garland’s name to the floor, and Lindsey was happy to oblige. But it was to go no further. With Lindsey’s lone defection, the GOP would vote Garland down, notch a big win, and leave President Gore with gobs of egg on his face.

That was the plan, at least. But plans have a way of unraveling, especially in politics. The Senate clerk called the roll, and Lindsey dutifully voted yes. But to his surprise, so did Elliot Cutler, the maverick independent from Maine. And then, in a moment that has since been dramatized by half a dozen showrunners and screenwriters, Arlen Specter, the five-term Republican from Pennsylvania, rose from his desk, balled up a fist, and turned up his thumb. Ninety-nine mouths fell open in shock. The final tally was fifty-fifty; Vice President Lieberman swooped in to break the tie, and Merrick Garland was America’s next Chief Justice.

The Garland vote plunged the Republican Party into full-on civil war. Glenn Beck called it a knife in America’s back. Tim LaHaye called it day one of the Great Tribulation. In his column in the National Review, Pat Buchanan declared “RINO hunting season,” and soon, every Republican involved in Garland’s confirmation had paid a price for it. Trent Lott was forced out as Majority Leader, to be replaced by the bomb-throwing Jim Inhofe. Senator Specter switched sides and became a Democrat, while Lindsey became public enemy number one for the nation’s evangelicals. His office got so much hate mail that he had to hire a full-time screener to sort through it all. James Dobson described a vision of Hell in which Lindsey writhed at the hands of fork-tongued demons, while Rush Limbaugh compared him to Xi Kinnear, the treacherous spy who sells out Captain Reynolds in season five of the Fox series Firefly.

By 2008, even Lindsey could tell his political career was dying, so he decided to martyr himself. When Mike Fair emerged once again to challenge him in the primary, Lindsey threw his back into the campaign even though it was clear he had no chance. He stumped across the country with his old pal John McCain, whose second presidential campaign was equally hopeless. When McCain inevitably dropped out, Lindsey crossed the aisle and endorsed Joe Lieberman for President; when Lieberman lost the Democratic nomination, Lindsey didn’t go quite so far as to endorse Hillary Clinton, but by election day, he was appearing twice a week on The Thom Hartmann Show to denounce the holy war and lament the state of his party. It didn’t do any good—the crusaders carried the day, and the crimson wave that spread across the country that night marked a rebuke of both Lindsey and his politics.

In 2009, Lindsey’s Senate term expired, and he trundled, aimless, back to Seneca. He tried to practice law again, but his good name was tarnished, and clients were scarce. Soon, he decided it was time for a fresh start. In 2010, Lindsey’s sister Darline was named CEO of a marketing agency in the oceanside town of Beaufort. Lindsey followed her downstate, and within two months, he’d fallen in love with the picturesque town. The quaint, palm-lined streets were a welcome foil to the soulless bustle of Washington, and the warm, friendly people were a relief after months of cold side-eyes in Seneca. With the help of some old friends in Congress, he found a new law firm where his pockmarked past didn’t matter so much, and within a few years, he’d earned a reputation as a brilliant divorce attorney. His services were in high demand among the Charleston glitterati, and his Hilton Head office entertained some of the most prominent socialites in the South.

“It hasn’t all been sunshine and rainbows, though,” he sighs, sweeping his brush across the canvas to evoke the morning light. In 2012, he met Patricia Altschul, a sharp-tongued, local art collector whose son was one of his clients. Two years later, they married, and two years after that, they split. Lindsey’s skill with the law kept his assets safe, but the divorce became front-page fodder for every tabloid from New York to New Orleans. Us Weekly ran a flashy piece on Lindsey’s failings as a husband; in one interview, Patricia reported that their house was so filthy, she’d once ruined a $3,000 Hermès dress by sitting on a peanut butter sandwich he’d left wedged between the couch cushions.

The hounding from the press left Lindsey humiliated. By the time the dust settled, all he wanted was to escape high society, so he moved his practice to the sleepy town of Ridgeland and bought thirty acres of coastal farmland in a remote corner of Port Royal Sound. Since then, he’s had one moment in the spotlight: when Alex Murdaugh, the local state’s attorney, was accused of embezzling public funds in 2021, Governor Knox White appointed Lindsey special prosecutor. Lindsey did his job with honor and distinction, and Murdaugh got fourteen years in prison. Aside from that, though, Lindsey’s life is pretty quiet. As far as I can tell, he cares as little about politics as he does about Irish river dancing. At one point in our conversation, I ask whether he thinks McInnis will win North Carolina next month, and he looks at me as if I’m speaking in ancient Sanskrit.

Lindsey still practices law from time to time, and he visits Darline and her family in Beaufort at least twice a month. These days, though, he spends most of his time hiking, fishing, and painting—lots of painting. He picked up the hobby while touring art galleries with Patricia, and ever since then, it’s been his pastime. In ten years, he says, he’s done more than four hundred tableaus, mostly of nature scenes up and down the Gullah coast. “It’s probably the one thing I don’t regret about that marriage,” he snorts, adding one last wisp of color to the cresting sun.

I look up from my notebook and drop my jaw, amazed. The blank canvas has blossomed, as if by magic, into a gorgeous, southern sunrise. Indian yellow streaks across the horizon. Leafy tufts of phthalo green cling tightly to the foreground. Stalks of Van Dyke brown shoot up from a saltwater cove that shimmers and sparkles in every color but blue.

Lindsey lifts the canvas off the easel and places it between my hands. I stare down, gripped by a sense of wonder I haven’t felt in forty years. “Know why art’s better than politics?” He asks, grinning. “No one ever calls you a Satanist after you hand them a painting.”

2000 Graham Framed NTB (1).png
 
Love the story so far. Who is McInnis meant to be is that representative Scott McInnis (that’s who google gave me)?
 
2001
October 4, 2024

It’s quarter to ten on a brisk, September morning. I’m in Newark, New Jersey, twenty minutes by train from downtown Manhattan, in a spacious, ground-floor office wedged between a liquor store and a nail salon. I sit in the corner, sipping Folgers from a paper cup, watching as the twenty-third Saturday Summit is gaveled into session.

The Summit’s twelve attendants sit at eight folding tables arranged into the shape of a square. They’re not diplomats or military commanders; they’re teens and twenty-somethings from the city’s impoverished wards, specifically chosen to represent their communities. They go around the circle, introducing themselves by name and neighborhood: “I’m Lashawny Foskin, and I’m from Vailsburg,” says one young man munching a Krispy Kreme cruller. “I’m Esme Pacheco, I’m from The Neck,” says a girl with black eye shadow and a heavy metal T-shirt. The introductions continue until only one man remains. “I’m Cory Booker,” he says, “and I’m from Central.”

Now, the Summit begins in earnest. Each delegate takes the floor to air a grievance shared by his or her community: Lashawny explains his neighbors’ fearful relationship with the police, while Esme laments that the trash piles up for weeks on her street before the city comes to clean it up. One delegate describes a playground that is constantly littered with syringes, while another reports that two people have been shot on his block in the past three months. From his seat, Cory watches with intense, compassionate eyes until the last delegate speaks her piece. Then, he rises to his feet and opens his mouth. “Everyone in this room has worth and value,” Cory announces, bald head towering over the room like a church cupola. “Your elected officials are your employees,” he declares, words bursting out of his mouth like firecrackers, “and you have the power to make them work for you.”

Over the past twenty-five years, Cory explains, he’s bent the government to his will time and time again with nothing but courage, faith, and indefatigable grassroots energy. He splits the delegates into small groups to discuss how they might apply these principles to their own lives. He gives them thirty minutes to form a plan, then ten minutes to sketch it out, then five minutes to present it to the group. I listen as ideas are exchanged, debated, and refined. Proposals are developed, analyzed, and developed again under Cory’s careful tutelage. To my amazement, as the seminar goes on, the delegates stand taller and speak louder, as if discovering a power they didn’t know they had. The feeling builds and builds until, finally, the clock strikes one, a tray of sandwiches appears, and the summit breaks for lunch. The delegates each grab a sub and peel off into cliques, while Cory walks up to me in the corner with a turkey club and a paper plate. “So,” he asks, smiling, “what do you think so far?”

By rights, Cory shouldn’t be here. He should be ten miles away on the other side of the Hudson, managing a law firm on the Upper West Side. Born and raised in the posh, leafy suburb of Harrington Park, Cory was a high school football star who went to Stanford on an athletic scholarship, then to Oxford on a Rhodes Scholarship, then finally to Yale Law School, where he graduated with a J.D. in 1997. With a resumé like that, he could have easily found himself a corner office somewhere and settled into a cushy life of riches and repose. But his conscience wouldn’t have allowed it. Cory’s parents (who were among the first black executives at IBM) fought hard for their civil rights, and they taught him a strong sense of civic responsibility that shaped his perspective on life. While classmates flocked to prestigious firms in New York or Washington, Cory set his sights on political activism, determined to use his mind to improve the world around him.

It was this determination that brought Cory to Newark. He moved here in 1997 to start an advocacy group for low-income families, and soon afterward, he had his first brush with local politics. Newark in those days was an old-school town run by old-school, machine politicians, and nothing ever got done unless it lined the pockets of someone powerful. Month after month, Cory would trek to City Hall to demand change, and they’d laugh in his face. So, he took matters into his own hands. In 1998, he ran for City Council and won, knocking a sixteen-year incumbent off his perch. Outnumbered eight to one, Cory couldn’t force the establishment to change, so he decided to shame it instead. He moved into Brick Towers, a blighted public housing project synonymous with poverty and neglect. He took pictures of potholed roads and mailed them out to his constituents. He pulled stunt after stunt to highlight Newark’s festering crime problem, including a ten-day hunger strike and a summer spent living in a motorhome on the city’s most dangerous streets.

Cory’s exploits attracted attention, but they weren’t enough. Newark’s schools remained a mess, its streets remained unsafe, and a third of its residents remained in poverty. Still, when Cory looked out across the city, he saw mountains of potential buried underneath its concrete plains. When I first interviewed him in 2001, he took me on a five-hour walking tour of his imagination: "this would be a great spot for a community center,” he declared, pointing to a vacant lot overgrown with weeds. “With the right tax incentives, this place could look like Fifth Avenue,” he dreamed as we walked down a street lined with boarded-up storefronts. “Imagine if Rutgers built a lecture hall here!” He exclaimed, beholding a block that had burned to the ground during the riots of 1967. Cory had been in Newark for less than five years, and yet, he seemed to believe in it more strongly than anyone else ever had. Six-foot-three with dress shoes and a long-tailed overcoat, he reminded me of a bald, black, beardless Abraham Lincoln, so excited by his words that he tripped over them in his haste.

As I wrote in The Atlantic, Cory’s vision for the city was far too vast for a lowly councilman to put into effect. During our walk, he mused that he might run for mayor in 2002; by the time my profile went to print, he’d all but made up his mind. It would be an uphill battle—the incumbent, Mayor Sharpe James, had been around for thirty-two years and had the entire establishment on his side—but Cory was determined. He launched his campaign in November of 2001, and instantly, his life became hell. The local press pelted him with insults. Policemen ripped down his signs, and businesses that dared display them were threatened and harassed. While Mayor James held huge rallies with the Governor and members of Congress, Cory walked the streets alone from dawn till dusk, knocking doors and shaking hands.

So it went, week after week. And then, there came a miracle. On January 5, Newark’s own Star-Ledger published a bombshell report that Mayor James had stolen $600,000 from the city through an elaborate real estate scam. Federal prosecutors charged the mayor with fraud, and seven days later, he resigned in disgrace. In his place, the City Council appointed a faceless deputy mayor whose name was even more obscure than Cory’s. suddenly, the race was blown wide open. In a city rocked by scandal, Cory’s fresh, youthful face now seemed attractive and enticing. His rallies got bigger and his donors’ checks got fatter. At long last, it seemed, an honest politician was getting his due.

By now, you’ve probably guessed what happened next. From my seat in the back, I scan the faces of the Saturday Summit delegates; by sight, none of them are old enough to remember where they were on the morning of February 12, 2002. The story of United Flight 175, and of the passengers whose heroism brought it down before it could reach the World Trade Center, has been told a thousand times. Lesser known is the horrified shock of the people of Newark, who looked up that day to see a commercial airliner crash headlong into their city’s baseball stadium.

In a single, fiery instant, 307 people died and thousands of Newarkers were traumatized. What they didn’t know then was that they had a leader—a strong leader. Within ten minutes of the crash, the interim mayor was on site, personally directing the rescue operation. By the time the National Guard arrived, he was bent down beside what remained of Riverfront Stadium, helping pull survivors out from under the rubble. Once it became clear that the crash was an attack and not an accident, the mayor spent hours in front of the TV cameras, fielding question after question with humanity and grace. All of a sudden, Newark’s part-time, caretaker mayor had a face and a name. The world had caught its first glimpse of Ras Baraka.

When the first plane went down, Cory wasn’t in Newark. He was at a fundraiser in Manhattan, schmoozing and boozing with hedge fund types. He tried to rush back home, but by that point, the North Tower had been hit and the city was on lockdown, so Cory spent the night at a friend’s house on the wrong side of the Hudson, eyes glued to the television screen. While New York Mayor Mark Green stumbled and stuttered in front of the cameras, Ras Baraka reached deep into his poet’s soul and came out with an address that galvanized the American people. “The men who committed this crime will be brought to justice,” Baraka declared, “no matter how long or how hard we must fight. We will rebuild, we will recover, and we will overcome.” By “we,” Baraka meant Newark, but he might as well have been speaking for the country as a whole. The former high school principal was the embodiment of American resolve. Cory could scarcely believe his eyes—in a matter of hours, his opponent had gone from faceless nobody to national hero.

By then, the race was all but over. For weeks after 2/12, Baraka was everywhere. He stood tall with Al Gore and shed tears with Oprah Winfrey. The media lavished him with praise, and Time put him on its cover. By March, every front lawn in Newark sported a “THANK YOU MAYOR RAS” sign, and in April, local artists turned the remnants of Riverfront Stadium into a mural in his honor. Cory, meanwhile, was left behind in the dust. His rallies became ghost towns and his donations dried up like a desert well. His sunny spirit never dimmed—right up until Election Day, he was out there on the streets, shaking hands and kissing babies—but it was no use. The votes were tallied up, and Cory lost four-to-one against America’s Mayor.

“After the election,” Cory recalls, munching on his BLT, “I got pretty bitter for a while.” It’s not hard to see why. Cory had spent four lonely, thankless years serving his community, and for one brief, shining moment, it looked like he’d have his reward. Then, suddenly, a cruel twist of fate had snatched it all away. Not only was he angry at the world, he was ashamed at his own anger (“I mean, at least I'd survived 2/12,” he tells me. “A lot of people weren’t that lucky”).

Cory spent the next few years bouncing around the Eastern Seaboard like a pinball: eight months at a lobbying firm in Trenton, three semesters teaching public policy at George Mason, a year and a half as co-counsel for a Boston nonprofit. When his old City Council seat came up for re-election in 2006, a few friends tried to persuade him to come back to Newark and run, but Cory declined; the wound still felt too fresh.

Eventually, though, things started looking up again. Cory moved to Brooklyn and found a job he liked at The Tiberius Project, helping veterans of Iraq make use of the G.I. Bill. For the first time in years, he felt content and secure, safe in the knowledge that he could help those in need while staying far, far away from the soul-sucking world of politics.

And then, Rick Santorum was elected president. 2008 didn’t mark Cory’s “awakening,” exactly, as it did for so many other progressive activists, but it did reaffirm his conviction that civic engagement is a duty and not a choice. In 2009, he moved back to Newark. He told himself he was just saving on rent, but within two months, he’d already dipped his toes into the local grassroots scene. In his time off from Tiberius, Cory organized rallies for HumaneNJ, a prisoners’ rights group which successfully persuaded then-Governor Michael Chertoff to sign a law abolishing New Jersey’s death penalty.

This victory brought Cory back into the public eye, and it also provided a bridge to one of his personal pet issues: education. In the wake of 2/12, Mayor Ras had used his star power to raise tens of millions of dollars for Newark’s struggling public schools, and yet, eight years later, graduation rates remained low and the district remained chronically underfunded. So, in 2010, Cory formed an advocacy group to push for more charter schools. The group blossomed thanks to Cory’s contacts in Trenton, and it attracted ample funds from philanthropists and charitable trusts (Cory nearly took four million dollars from E.W. Jackson’s Department of Education, but pulled back once it became clear that taking federal money meant mandatory classes with names like “Sexual Morality” and “Biblical Principles”).

By 2013, Cory had helped three new charter schools open their doors in Newark. Still, he couldn’t shake the feeling that he hadn’t done enough. Over the course of his work, he’d met with parents, students and community leaders who made him realize that real change meant more than just improving the quality of the schools themselves. “I really got a sense of how deep the problems go,” he recalls. “We’d give out netbooks to the kids so they could do their homework, but some of them didn’t have electricity at home a lot of the time, let alone internet access. We’d send school buses to pick up the kids, but the mothers were afraid to let them on because the routes went through gang territory.”

Over time, Cory began to see that fixing education in Newark meant bettering the lives of the city’s youth in a concrete, lasting way. So, in 2013, with a grant from the Technology Access Foundation, he bought an empty office on Bergen Street and turned it into Community Club Central, an establishment that was “part library, part civic center, part fun,” as he explained to the Star-Ledger on opening day. The Club had computers, textbooks and tutors to help students with their homework, plus an outdoor playground and a wide selection of board games. It organized cookouts and block parties in the summer and offered remedial courses for high schoolers looking to enroll in community college.

Instantly, the Club exploded in popularity. Each week, hundreds of kids packed its spacious walls, and soon, grown-ups started showing up, too. The Club pulled in donations from charities all around the country, and soon, Cory quit his job at Tiberius to run it full-time. In 2014, he started a summer program for teenagers to earn money cleaning public parks and staffing food banks. That September, when Hurricane Rene ravaged South Jersey, he took three buses of volunteers down to help with the cleanup. In 2015, as crime rates spiked nationwide and shootings ravaged Newark’s streets, Cory helped train dozens of so-called “violence interrupters”—professional mediators skilled at brokering peace. At a time when much of American civic life ran through the evangelical church, Cory’s efforts united Newarkers of all creeds and colors without the need for a common faith.

Since then, the Club’s stature has risen even further. In 2016, while the Amara Brownlee riots raged across the country, the Club hosted talks between protesters and the police that helped Newark avoid wholesale destruction. Three years later, after local peace activist Jayda Jacques was shot dead in the street, the Club helped organize a ceasefire between rival gang sets that cut the city’s murder rate by over 25%. The relationships formed that day proved durable, and soon afterward, delegates assembled for the first-ever Saturday Summit. The Summit started off as Cory’s brainchild, as his way of bringing together young people who might otherwise have never met. Since then, they’ve grown into a local institution. Every other month since 2019, twelve bright, young Newarkers have gathered under Cory’s patient eye to hear and be heard, to learn and to educate.

Cory’s activism has made him a local celebrity. In 2021, New Jersey Monthly named him the 18th most influential person in the state, and last year, President McInnis invited him to the White House to receive a Points of Light Award. If Cory has a personal life, he doesn’t let it show; at fifty-five, he’s still a bachelor. “I’m married to the job,” he admits. “I’ve had a few relationships, but nothing too long-term.” As for another foray into politics? “Right now, that’s pretty unlikely.” In the 2010s, Cory’s charter school advocacy put him firmly at odds with the Newark teachers’ union and, by extension, with Ras Baraka (himself a former teacher). Even though Mayor Ras resigned ten years ago to take a seat in Congress, his power in Newark is such that it would take a miracle for Cory to win anything. “I’m a perennial outsider,” Cory confesses with a smile, “but that’s okay. I’ve made more of an impact running this club than I ever could have in politics, even if I’d been Mayor for a hundred years.” His name may not count for much in City Hall, but on the streets, it’s solid gold.

Cory looks down at his watch: 1:50. The trashcan has filled up with sub wrappers and mustard packets. In ten minutes, the Summit will resume. I’m welcome to stick around, Cory says, but from here on out, he won’t be very talkative (we’ve entered the “listening” phase, he explains). I take the hint. With a firm handshake and a warm smile, I thank Cory for his time, excuse myself, and step outside into the cool, autumn air.

I booked a late train home, so I take my time getting back to the station. The walk makes me feel like a traveler in an antique land. I amble up Bergen Street past rusting cars and heaps of faded masonry. I stroll down Market Street past dingy storefronts and shabby office parks. Here and there, I spot something that grounds me in the present—a Morgan sign in someone’s front window, a Sunshop showing off the latest Praxis, Christian Pulisic’s face on a Nike ad.

Eventually, I find myself in Riverfront Park, where the victims of Flight 175 are memorialized. I wander through a forest of stark, metal totems, one for every victim of the crash. I run my fingers over the surface of the monument, feeling the names etched into the smooth, black granite. I walk into the center, where two model Twin Towers jut up like trunkless legs of stone. I look up at the Riverfront Mural and see the sagely face of Mayor Ras, his nine most famous words swirling around him: “WE WILL REBUILD, WE WILL RECOVER, WE WILL OVERCOME”.

I look around. Ras was right—Newark today bears little trace of the shell shock that marred it twenty-two years ago. But neither is it a land of milk and honey. Compared to other Americans, Newarkers are still twice as likely to die by violence, twice as likely to be unemployed, and three times as likely to live in poverty. If Mayor Ras hasn’t turned things around after so many years in power, is there anyone who can?

I turn back to the mural and take a closer look. Time has taken its toll—the paint is flaking, the color is fading, and the brickwork is chipping away. Suddenly, it hits me: there will come a day, many years from now, when Cory and Ras exist only in the minds of today’s children. The children of today weren’t around to see Ras’s heroism on 2/12; these days, if they see him at all, it’s as Congressman Baraka, a faraway figure on Plaxo or CoffeeShop. Cory, on the other hand, is a constant presence in their lives, hearing their struggles, offering his counsel, and nurturing their sense of civic virtue. I won’t be around to see how either man is memorialized, but if I had to guess, I’d say that Ras will be known for a moment of greatness followed by decades of simple adequacy, while Cory will be known for a moment of failure followed by decades of passionate, dedicated service.

I think I know which legacy I’d rather leave behind.

2001 Booker Framed NTB (1).png
 
Last edited:
2002
October 18, 2024

I’ve never been much of a wine drinker. Every glass I’ve ever had has tasted like vinegar mixed with antifreeze. I dread the yearly Atlantic staff dinner because my editor always orders a vintage red for the table, and when she inevitably asks my opinion, I’m so ashamed of my ignorance that I start fumbling around for random adjectives (some recent favorites: “resinous,” “schmaltzy,” and “orgasmic”).

So, when my fourth star sits me down and offers me a taste of Merlot from his Napa Valley vineyard, a pang of panic hits my side. I grow bewildered as he shows me the label, which is a dizzying stew of nouns and adjectives (“Aetherium Quantum Vinum: Precision-engineered for the future-focused palate with synergistic infusions of saffron and oak”). I hide my nerves behind a smile as he fits a futuristic handle over the cork and pops it out with the press of a button. I feel my palms start to sweat as he tips the bottle and the dark, crimson liquid comes pouring out. I grip the glass by the stem and try desperately to recall the steps I learned from Alexandra Starzyk, wine critic for the Boston Globe: swirl it around (“aeration,” I think that’s called), give it a whiff (“aroma”? “bouquet”?), and then, finally, taste. I lift the glass to my mouth, curl my lips around the rim, and…

Oh. That’s just…flat. Basic. Bland, even. A simple, uncomplicated profile, like alcoholic Nesquik. Surely, it’s just my primitive palate that’s the problem, right? I take another sip, and...

Uhh, nope. It’s not just me. This tastes like Two Buck Chuck on an off day. I look up at my host, who stares back down with a wide, plasticky grin. “See?” He says. “I told you. We’re the disruptors.”

Whatever else you might say about him, Gavin Newsom is a very handsome man. Sharp-jawed and tanned with chiseled features and shoulder-length, silver hair, he’s like a cross between Eric Dane in Hard Case and Timothy Olyphant in Have Gun, Will Travel (although the Patagonia vest does detract a bit from his ruggedness). If he seems well-heeled, that’s because he is—Gavin is the chairman of a venture capital firm, and Fortune pegged his net worth at $2.3 billion last year. But that hasn’t always been the case. Gavin was born and raised in San Francisco, where his father, Bill, was a well-respected appellate court judge with a heart far too big for his wallet. “Dad was mission-driven,” Gavin recalls, pouring himself a glass of Aetherium. “He believed that if there are people in need, you help them, period. He never made much money to begin with, and a lot of what we had, he gave away. Most of my mom and dad’s fights were about money.”

When Gavin was five, his parents divorced, and his mother worked three jobs to support her two children. Gavin’s struggles were compounded by dyslexia, which kept him out of the Bay Area’s prestigious prep schools, and as a teenager, he spent weekends and summers working to make ends meet. “From the day I was born,” he says, sipping his swill, “it was nothing but hustle, hustle, hustle.”

But Gavin had one thing most poor kids don’t (and which he seems in no hurry to mention to me now): connections. Bill Newsom may not have been rich, but his web of contacts was among the widest in the state—he was close with the billionaire Gordon Getty, and many of San Francisco’s top lawyers and businessmen were in his circle. These relationships would become young Gavin’s safety net. When Gavin struggled to pay for college, Bill called up a friend at Santa Clara University and got his son a scholarship. After graduation, when Gavin decided to start his own business, he found an eager partner in Gordon Getty, whose endless wealth allowed Gavin to open a wine shop on Fillmore Street called PlumpJack.

To Gavin’s credit, he held his own as a businessman. PlumpJack did well enough to satisfy its investors, and with the help of more Getty money, it quickly grew into an empire of cafés, bars, restaurants, hotels, and wineries. Soon, Gavin was rich, and his newfound wealth gave him an easy bridge into politics. He hosted fundraisers for Willie Brown, a veteran politician who was elected Mayor of San Francisco in 1995. Always one to reward his friends, Brown appointed Gavin to a vacant seat on the city’s Board of Supervisors, where, surrounded by aging hippies and crusty progressives, he carved out a niche as a youthful, fresh-faced businessman with common-sense solutions to the city’s woes.

Gavin’s sensible persona endeared him to Mayor Brown, who was frantic to appeal to business in the wake of the dot-com crash. His signature achievement was an initiative that cut cash payments to the homeless while beefing up shelters, counseling, and other social services; leftists lambasted this measure as cruel and cold-blooded, but it made Gavin a darling for centrists and moderates. As time went on, Gavin’s links to Brown grew tighter and tighter, and soon, rumor had it he was being groomed for the mayor’s chair himself.

It was in this context that I singled Gavin out for my list. The choice made logical sense—Gavin’s profile was high enough already, and his rise would epitomize the triumph of Clinton-Gore centrism at the cradle of American counterculture. Yet I can see now that I was hedging my bets. By the time Gavin and I met, Rising Stars was entering its fourth year, and I was starting to lose faith in my own experiment. Not two months earlier, Cory Booker’s crusade against the Newark machine had fallen apart at the finish line. I’d bet on the underdog once, and I’d regretted it so sorely that when the time came to choose again, I chose a man who couldn’t possibly lose: a San Francisco Democrat with the backing of the establishment.

In June of 2002, I met Gavin for dinner at a chic Italian spot on Fisherman’s Wharf. Everything about him screamed California nouveau-riche: his neat, gelled-back hair, his Ralph Lauren suit, his careful perusal of the wine list and eventual selection of a ‘96 Alto Adige. Between bites of tagliatelle, he rattled off his liberal credentials and marveled that they didn’t buy him more credit (“only in San Francisco can you be pro-choice, pro-gay marriage, pro-gun control, pro-rent control and still be called a conservative”). He had no shortage of bright ideas for the city, all of which sounded like mystery authors, movie titles, or pro wrestling moves (“S.F. Shines”; “Operation Mission Impossible”; “The Tenderloin Scrubdown”). He was newly wed, but his wife Kimberly was absent—their marriage was long-distance, with Gavin anchored in the Bay while she pursued a career in New York. As I watched him down his fourth glass of wine, it occurred to me that Gavin was tailor-made for his time and place. In another decade, they’d have called him a yuppie. In another city, they’d have called him an elitist. But in early-2000s Northern California, he was the platonic ideal of electability.

Sure enough, as soon as Gavin kicked off his run for mayor in 2003, he became top dog. His ties to wealth and power paid massive dividends, and he piled up big-ticket endorsements from all over the state. His dominance was so complete that his most significant opponent was a member of the Green Party. To the press, Gavin was as good as elected. After all, what Democrat could possibly lose in San Francisco?

But in the San Fran of 2003, there was a groundswell of discontent that the chattering classes failed to notice. On Willie Brown’s watch, rents had skyrocketed and homelessness had festered, disillusioning the voters with business as usual. There were broader forces at work, too—Meg Whitman’s win in the 2002 governor’s race had demoralized California liberals, while the invasion of Iraq had left young progressives frustrated and alienated from the Democratic Party. Gavin’s Green Party opponent, Matt Gonzalez, was not some nameless crank but the President of the Board of Supervisors, and what he lacked in campaign cash he more than made up for in good looks and charisma. Later on, historians would point out Gonzalez as an early prophet for the coarse, salty populism that would sweep the nation during the 2010s.

Even so, Gavin likely would have won. But then, three weeks before election day, the National Enquirer published a photo of Gavin stumbling out of a bar in the Mission District with a woman who was quite emphatically not his wife. Gavin played it off, saying that the woman was a campaign advisor, that they’d met to discuss strategy, and that the stumble was nothing more than a momentary loss of balance (“I had a great optics team back then,” Gavin recalls). The response worked, and the story had just started to fade from the headlines when the San Francisco Chronicle published an exposé that included three momentous revelations: one, that the woman was not an advisor but the wife of Gavin’s campaign manager; two, that they were having an affair; and three, that Gavin’s stumble was caused not by a crack in the sidewalk but by his longtime addiction to alcohol.

At this point in the story, I can’t help but notice how carefully Gavin has been nursing that glass of Merlot. He catches my eye. “Follow me,” he says, setting his glass down on the bar. “I want to show you something.” I trail him outside into the warm, Napa Valley sun. We climb into a doorless Jeep and he steers us past row after row of flowering vines, silver hair flapping wildly in the wind. Purple grapes glisten like beads of frosted glass, and workers in silver polo shirts pluck at the stems with computerized shears.

“After the Chronicle thing broke,” Gavin shouts above the roar of the engine, “I had probably the worst year of my life!” From what I can tell, he’s not exaggerating. The cheating and the alcoholism shattered Gavin’s reputation, and when the ballots were counted on election day, Gonzalez won by more than seventeen thousand votes. Three days later, Kimberly filed for divorce, leaving Gavin to fight for control of his assets while seeking treatment for an addiction he could barely admit to himself that he had. By the time Gavin emerged from a five-month stint in rehab, his businesses were crumbling, and lawyers’ fees had eaten up so much of his wealth that he could no longer afford to live in San Francisco. Desperate, he sold his million-dollar house in Pacific Heights, found a studio in Sunnyvale, and buckled down to save what was left of his fortune.

The Jeep rolls to a stop outside a squat, stucco hut on the outskirts of the vineyard. “That,” says Gavin as he steps down from the driver’s seat, “is when I pivoted.”

By 2004, the winery was almost bankrupt, and Gavin was frantically searching for something new and fresh to keep it afloat. Friends in Silicon Valley introduced him to Jawed Karim, a young software engineer who’d been forced out of his job at PayPal by then-CEO Peter Thiel. Over hash and eggs, Karim laid out his pitch for an e-commerce platform that would allow PlumpJack to ship its wine anywhere in North America. Gavin was skeptical, but in the end, he bit. “This kid was just…different, you know?” He explains, talking with his hands like Jack Woltz in The Godfather. “I mean, he was a unicorn. He was scrappy. He had drive. He reminded me so much of myself!”

Within a year, Karim’s algorithm had transformed PlumpJack into the third-best selling label in California. Karim soon started a company of his own, and when Amazon bought it in 2007, Gavin’s twenty-percent stake made him a millionaire many times over. By that time, Gavin’s business was doing so well that he’d started buying up other wineries, and yet his side gig as an investor was taking up more and more of his attention. “I discovered that I have a gift for picking out innovators,” Gavin boasts as I follow him into the stucco hut. “Everything I touched turned to gold. I was like King Midas for tech.” Through Karim, Gavin got to know various other PayPal refugees with bright ideas of their own. In 2005, he founded PlumpJack Ventures, whose early investments later became some of the nation’s most recognizable tech brands. Among them: Imladris, which was one of the largest social networks in America during the early 2010s; SolTek, a leading green energy firm; and Sidework, an app which allows retail and restaurant managers to quickly replace fired workers by picking from a pool of local profiles.

By 2013, Gavin had fully embraced his second life as a full-time venture capitalist. He sold his stake in everything but the winery and the investment fund, grew out his hair, and bought entire closets’ worth of fleece vests and khaki slacks. He bought mansions in Palo Alto and the Riviera, dined on coq au vin at The French Laundry with his partners, and played squash at Equinox with startup founders. That June, he attended a gala where he met Marissa Mayer, a senior executive at Plaxo. Two years later, they married (I don’t get to meet her, though—the day I visit, she’s off at a shareholders’ conference in San Diego).

In 2016, Gavin officially became a billionaire. By that point, his bout with politics was so far in the past that it felt like a dream. “For years after I lost,” Gavin smirks, leading me down a winding flight of stairs, “they treated me like a punchline. No one wanted anything to do with me. Then, I got rich. Suddenly, every politician in the country was begging for my number.” I don’t even bother asking whether he’d ever run for office again; I’ve never met a politician with a ten-figure salary, or one who’s allowed to day-drink in front of a journalist.

That doesn’t mean, though, that he’s lost interest in politics. Over the last ten years, Gavin has become one of California’s most prolific political donors, and like most big-tech figures, his party preference changes from cycle to cycle. In 2014, he endorsed Democratic Governor Jeff Morales for re-election, but four years later, he turned around and gave $800,000 to Republican candidate (now Governor) Lanhee Chen. In 2016, Gavin declined to endorse Keith Ellison on the grounds that he was “regressive” and “anti-innovation,” and in 2020, he supported Scott McInnis for President. This year, though, he switched sides once again with a $2 million donation to the Morgan campaign. When I ask why, he pauses on a step, sighs, and shakes his head. “McInnis has good ideas, but he can’t execute. He pledged green investment and bleeding-edge tech policy. It was one hundred percent fluff.” As for the constant flip-flopping? Gavin leans back, scratches his stubbly chin, and smiles. “I like optionality.”

At last, Gavin steps off the final stair and into a bright, spacious basement. He leads me into the corner, where I see a sleek, metal device that looks like a cross between an espresso machine and a pipe organ. Gavin reaches out and starts stroking the device with a gentle, admiring hand.

“This,” he explains, “is the Vine-o-Matic. Ever heard of Sirius Cybernetics?” He asks. I have; last month, Forbes ran a piece on their turtleneck-wearing founder, Lizzie Holmes.

“We were their incubator,” Gavin says, beaming with pride. “This is their newest prototype. You give it a blood sample, it does a spectroscopic analysis of your DNA, then gives you a blend of different wines that’s perfectly suited to your tastes,” he explains. “It’s helped with my sobriety like nothing else I’ve ever tried.” From his pocket, he produces a shiny, chrome-plated lancet. “Wanna see?”

Morbid curiosity seizes control of my hand. I watch, detached from my body, as Gavin pricks my thumb, squeezes a droplet of blood into a tiny, plastic tray, and feeds it into the machine. He does the same to his own thumb, then flips a switch. The machine whirs, then whines, then whizzes. After a minute, it dings, and a button lights up which reads Drink. Gavin reaches out, plucks two wine glasses off a shelf, and sets them up beneath the spigots. He presses the button and a ruby-red liquid drips into each glass.

Gavin hands me one, picks up the other, then brings it to his nose and takes in the aroma. I raise mine to my lips, tip the liquid into my mouth, and swallow. It tastes almost exactly like purple Kool-Aid.

When I arrived here today, I expected to come face-to-face with a human serpent. In preparation for our chat, I’d spent weeks poring over Gavin’s multitude of media appearances. I’d found his TED Talk on CoffeeShop and watched it seven times. I’d scoured his Fiver feed with a fine-tooth comb and listened to all forty-eight of his podcast appearances. Each time, the constant duplicity had left me stunned. Over and over again, Gavin would describe his impoverished childhood and his dramatic hustle to the top, but leave out the part where his dad was best friends with a billionaire. He’d explain the national, state, and local trends that caused him to lose the mayor’s race in 2003, but somehow manage to omit the words “adultery” and “alcoholism”.

I’ve felt the same way as this interview has progressed. When Gavin recalled the way in which his bold, singular vision saved PlumpJack from collapse, he seemed to forget that between 2004 and 2005, Gordon Getty’s share of the company leapt from 49% to 85% (a fact that I gleaned from state records). When he told me the story of his incredible success as a venture capitalist, he neglected to mention that he’d started investing at the best possible time: right after the In-Q-Tel scandal, when Washington and Wall Street were running scared from tech stocks and every startup in Silicon Valley was desperate for cash. This whole time, I’ve been scrutinizing Gavin’s words, trying to sniff out the lies and burrow through to the man inside.

But, as I watch him close his eyes, breathe in deep, and savor the bouquet of a wine that’s about as complex as an IKEA desk chair, it suddenly hits me: there is no man inside. With Gavin, what you see is what you get. He really, truly believes that fancy mission statements are the key to fine viticulture, and he really, truly believes that he rose up from poverty through nothing else but his own hard work and ingenuity. The story he tells isn’t a carefully-crafted web of deception—to him, it’s as real as the nose on his face.

Satisfied with the bouquet, Gavin smiles. “Bottoms up!” He cheers, and we clink glasses. I raise mine to my lips. After all, there’s no sense wasting good Kool-Aid.

2002 Newsom Framed NTB (1).png
 
Last edited:
October 18, 2024

I’ve never been much of a wine drinker. Every glass I’ve ever had has tasted like vinegar mixed with antifreeze. I dread the yearly Atlantic staff dinner because my editor always orders a vintage red for the table, and when she inevitably asks my opinion, I’m so ashamed of my ignorance that I start fumbling around for random adjectives (some recent favorites: “resinous,” “schmaltzy,” and “orgasmic”).

So, when my fourth star sits me down and offers me a taste of Merlot from his Napa Valley vineyard, a pang of panic hits my side. I grow bewildered as he shows me the label, which is a dizzying stew of nouns and adjectives (“Aetherium Quantum Vinum: Precision-engineered for the future-focused palate with synergistic infusions of saffron and oak”). I hide my nerves behind a smile as he fits a futuristic handle over the cork and pops it out with the press of a button. I feel my palms start to sweat as he tips the bottle and the dark, crimson liquid comes pouring out. I grip the glass by the stem and try desperately to recall the steps I learned from Alexandra Starzyk, wine critic for the Boston Globe: swirl it around (“aeration,” I think that’s called), give it a whiff (“aroma”? “bouquet”?), and then, finally, taste. I lift the glass to my mouth, curl my lips around the rim, and…

Oh. That’s just…flat. Basic. Bland, even. A simple, uncomplicated profile, like alcoholic Nesquik. Surely, it’s just my primitive palate that’s the problem, right? I take another sip, and...

Uhh, nope. It’s not just me. This tastes like Two Buck Chuck on an off day. I look up at my host, who stares back down with a wide, plasticky grin. “See?” He says. “I told you. We’re the disruptors.”

Whatever else you might say about him, Gavin Newsom is a very handsome man. Sharp-jawed and tanned with chiseled features and shoulder-length, silver hair, he’s like a cross between Eric Dane in Hard Case and Timothy Olyphant in Have Gun, Will Travel (although the Patagonia vest does detract a bit from his ruggedness). If he seems well-heeled, that’s because he is—Gavin is the chairman of a venture capital firm, and Fortune pegged his net worth at $2.3 billion last year. But that hasn’t always been the case. Gavin was born and raised in San Francisco, where his father, Bill, was a well-respected appellate court judge with a heart far too big for his wallet. “Dad was mission-driven,” Gavin recalls, pouring himself a glass of Aetherium. “He believed that if there are people in need, you help them, period. He never made much money to begin with, and a lot of what we had, he gave away. Most of my mom and dad’s fights were about money.”

When Gavin was five, his parents divorced, and his mother worked three jobs to support her two children. Gavin’s struggles were compounded by dyslexia, which kept him out of the Bay Area’s prestigious prep schools, and as a teenager, he spent weekends and summers working to make ends meet. “From the day I was born,” he says, sipping his swill, “it was nothing but hustle, hustle, hustle.”

But Gavin had one thing most poor kids don’t (and which he seems in no hurry to mention to me now): connections. Bill Newsom may not have been rich, but his web of contacts was among the widest in the state—he was close with the billionaire Gordon Getty, and many of San Francisco’s top lawyers and businessmen were in his circle. These relationships would become young Gavin’s safety net. When Gavin struggled to pay for college, Bill called up a friend at Santa Clara University and got his son a scholarship. After graduation, when Gavin decided to start his own business, he found an eager partner in Gordon Getty, whose endless wealth allowed Gavin to open a wine shop on Fillmore Street called PlumpJack.

To Gavin’s credit, he held his own as a businessman. PlumpJack did well enough to satisfy its investors, and with the help of more Getty money, it quickly grew into an empire of cafés, bars, restaurants, hotels, and wineries. Soon, Gavin was rich, and his newfound wealth gave him an easy bridge into politics. He hosted fundraisers for Willie Brown, a veteran politician who was elected Mayor of San Francisco in 1995. Always one to reward his friends, Brown appointed Gavin to a vacant seat on the city’s Board of Supervisors, where, surrounded by aging hippies and crusty progressives, he carved out a niche as a youthful, fresh-faced businessman with common-sense solutions to the city’s woes.

Gavin’s sensible persona endeared him to Mayor Brown, who was frantic to appeal to business in the wake of the dot-com crash. His signature achievement was an initiative that cut cash payments to the homeless while beefing up shelters, counseling, and other social services; leftists lambasted this measure as cruel and cold-blooded, but it made Gavin a darling for centrists and moderates. As time went on, Gavin’s links to Brown grew tighter and tighter, and soon, rumor had it he was being groomed for the mayor’s chair himself.

It was in this context that I singled Gavin out for my list. The choice made logical sense—Gavin’s profile was high enough already, and his rise would epitomize the triumph of Clinton-Gore centrism at the cradle of American counterculture. Yet I can see now that I was hedging my bets. By the time Gavin and I met, Rising Stars was entering its fourth year, and I was starting to lose faith in my own experiment. Not two months earlier, Cory Booker’s crusade against the Newark machine had fallen apart at the finish line. I’d bet on the underdog once, and I’d regretted it so sorely that when the time came to choose again, I chose a man who couldn’t possibly lose: a San Francisco Democrat with the backing of the establishment.

In June of 2002, I met Gavin for dinner at a chic Italian spot on Fisherman’s Wharf. Everything about him screamed California nouveau-riche: his neat, gelled-back hair, his Ralph Lauren suit, his careful perusal of the wine list and eventual selection of a ‘96 Alto Adige. Between bites of tagliatelle, he rattled off his liberal credentials and marveled that they didn’t buy him more credit (“only in San Francisco can you be pro-choice, pro-gay marriage, pro-gun control, pro-rent control and still be called a conservative”). He had no shortage of bright ideas for the city, all of which sounded like mystery authors, movie titles, or pro wrestling moves (“S.F. Shines”; “Operation Mission Impossible”; “The Tenderloin Scrubdown”). He was newly wed, but his wife Kimberly was absent—their marriage was long-distance, with Gavin anchored in the Bay while she pursued a career in New York. As I watched him down his fourth glass of wine, it occurred to me that Gavin was tailor-made for his time and place. In another decade, they’d have called him a yuppie. In another city, they’d have called him an elitist. But in early-2000s Northern California, he was the platonic ideal of electability.

Sure enough, as soon as Gavin kicked off his run for mayor in 2003, he became top dog. His ties to wealth and power paid massive dividends, and he piled up big-ticket endorsements from all over the state. His dominance was so complete that his most significant opponent was a member of the Green Party. To the press, Gavin was as good as elected. After all, what Democrat could possibly lose in San Francisco?

But in the San Fran of 2003, there was a groundswell of discontent that the chattering classes failed to notice. On Willie Brown’s watch, rents had skyrocketed and homelessness had festered, disillusioning the voters with business as usual. There were broader forces at work, too—Meg Whitman’s win in the 2002 governor’s race had demoralized California liberals, while the invasion of Iraq had left young progressives frustrated and alienated from the Democratic Party. Gavin’s Green Party opponent, Matt Gonzalez, was not some nameless crank but the President of the Board of Supervisors, and what he lacked in campaign cash he more than made up for in good looks and charisma. Later on, historians would point out Gonzalez as an early prophet for the coarse, salty populism that would sweep the nation during the 2010s.

Even so, Gavin likely would have won. But then, three weeks before election day, the National Enquirer published a photo of Gavin stumbling out of a bar in the Mission District with a woman who was quite emphatically not his wife. Gavin played it off, saying that the woman was a campaign advisor, that they’d met to discuss strategy, and that the stumble was nothing more than a momentary loss of balance (“I had a great optics team back then,” Gavin recalls). The response worked, and the story had just started to fade from the headlines when the San Francisco Chronicle published an exposé that included three momentous revelations: one, that the woman was not an advisor but the wife of Gavin’s campaign manager; two, that they were having an affair; and three, that Gavin’s stumble was caused not by a crack in the sidewalk but by his longtime addiction to alcohol.

At this point in the story, I can’t help but notice how carefully Gavin has been nursing that glass of Merlot. He catches my eye. “Follow me,” he says, setting his glass down on the bar. “I want to show you something.” I trail him outside into the warm, Napa Valley sun. We climb into a doorless Jeep and he steers us past row after row of flowering vines, silver hair flapping wildly in the wind. Purple grapes glisten like beads of frosted glass, and workers in silver polo shirts pluck at the stems with computerized shears.

“After the Chronicle thing broke,” Gavin shouts above the roar of the engine, “I had probably the worst year of my life!” From what I can tell, he’s not exaggerating. The cheating and the alcoholism shattered Gavin’s reputation, and when the ballots were counted on election day, Gonzalez won by more than seventeen thousand votes. Three days later, Kimberly filed for divorce, leaving Gavin to fight for control of his assets while seeking treatment for an addiction he could barely admit to himself that he had. By the time Gavin emerged from a five-month stint in rehab, his businesses were crumbling, and lawyers’ fees had eaten up so much of his wealth that he could no longer afford to live in San Francisco. Desperate, he sold his million-dollar house in Pacific Heights, found a studio in Sunnyvale, and buckled down to save what was left of his fortune.

The Jeep rolls to a stop outside a squat, stucco hut on the outskirts of the vineyard. “That,” says Gavin as he steps down from the driver’s seat, “is when I pivoted.”

By 2004, the winery was almost bankrupt, and Gavin was frantically searching for something new and fresh to keep it afloat. Friends in Silicon Valley introduced him to Jawed Karim, a young software engineer who’d been forced out of his job at PayPal by then-CEO Peter Thiel. Over hash and eggs, Karim laid out his pitch for an e-commerce platform that would allow PlumpJack to ship its wine anywhere in North America. Gavin was skeptical, but in the end, he bit. “This kid was just…different, you know?” He explains, talking with his hands like Jack Woltz in The Godfather. “I mean, he was a unicorn. He was scrappy. He had drive. He reminded me so much of myself!”

Within a year, Karim’s algorithm had transformed PlumpJack into the third-best selling label in California. Karim soon started a company of his own, and when Amazon bought it in 2007, Gavin’s twenty-percent stake made him a millionaire many times over. By that time, Gavin’s business was doing so well that he’d started buying up other wineries, and yet his side gig as an investor was taking up more and more of his attention. “I discovered that I have a gift for picking out innovators,” Gavin boasts as I follow him into the stucco hut. “Everything I touched turned to gold. I was like King Midas for tech.” Through Karim, Gavin got to know various other PayPal refugees with bright ideas of their own. In 2005, he founded PlumpJack Ventures, whose early investments later became some of the nation’s most recognizable tech brands. Among them: Imladris, which was one of the largest social networks in America during the early 2010s; SolTek, a leading green energy firm; and Sidework, an app which allows retail and restaurant managers to quickly replace fired workers by picking from a pool of local profiles.

By 2013, Gavin had fully embraced his second life as a full-time venture capitalist. He sold his stake in everything but the winery and the investment fund, grew out his hair, and bought entire closets’ worth of fleece vests and khaki slacks. He bought mansions in Palo Alto and the Riviera, dined on coq au vin at The French Laundry with his partners, and played squash at Equinox with startup founders. That June, he attended a gala where he met Marissa Mayer, a senior executive at Plaxo. Two years later, they married (I don’t get to meet her, though—the day I visit, she’s off at a shareholders’ conference in San Diego).

In 2016, Gavin officially became a billionaire. By that point, his bout with politics was so far in the past that it felt like a dream. “For years after I lost,” Gavin smirks, leading me down a winding flight of stairs, “they treated me like a punchline. No one wanted anything to do with me. Then, I got rich. Suddenly, every politician in the country was begging for my number.” I don’t even bother asking whether he’d ever run for office again; I’ve never met a politician with a ten-figure salary, or one who’s allowed to day-drink in front of a journalist.

That doesn’t mean, though, that he’s lost interest in politics. Over the last ten years, Gavin has become one of California’s most prolific political donors, and like most big-tech figures, his party preference changes from cycle to cycle. In 2014, he endorsed Democratic Governor Jeff Morales for re-election, but four years later, he turned around and gave $800,000 to Republican candidate (now Governor) Lanhee Chen. In 2016, Gavin declined to endorse Keith Ellison on the grounds that he was “regressive” and “anti-innovation,” and in 2020, he supported Scott McInnis for President. This year, though, he switched sides once again with a $2 million donation to the Morgan campaign. When I ask why, he pauses on a step, sighs, and shakes his head. “McInnis has good ideas, but he can’t execute. He pledged green investment and bleeding-edge tech policy. It was one hundred percent fluff.” As for the constant flip-flopping? Gavin leans back, scratches his stubbly chin, and smiles. “I like optionality.”

At last, Gavin steps off the final stair and into a bright, spacious basement. He leads me into the corner, where I see a sleek, metal device that looks like a cross between an espresso machine and a pipe organ. Gavin reaches out and starts stroking the device with a gentle, admiring hand.

“This,” he explains, “is the Vine-o-Matic. Ever heard of Sirius Cybernetics?” He asks. I have; last month, Forbes ran a piece on their turtleneck-wearing founder, Lizzie Holmes.

“We were their incubator,” Gavin says, beaming with pride. “This is their newest prototype. You give it a blood sample, it does a spectroscopic analysis of your DNA, then gives you a blend of different wines that’s perfectly suited to your tastes,” he explains. “It’s helped with my sobriety like nothing else I’ve ever tried.” From his pocket, he produces a shiny, chrome-plated lancet. “Wanna see?”

Morbid curiosity seizes control of my hand. I watch, detached from my body, as Gavin pricks my thumb, squeezes a droplet of blood into a tiny, plastic tray, and feeds it into the machine. He does the same to his own thumb, then flips a switch. The machine whirs, then whines, then whizzes. After a minute, it dings, and a button lights up which reads Drink. Gavin reaches out, plucks two wine glasses off a shelf, and sets them up beneath the spigots. He presses the button and a ruby-red liquid drips into each glass.

Gavin hands me one, picks up the other, then brings it to his nose and takes in the aroma. I raise mine to my lips, tip the liquid into my mouth, and swallow. It tastes almost exactly like purple Kool-Aid.

When I arrived here today, I expected to come face-to-face with a human serpent. In preparation for our chat, I’d spent weeks poring over Gavin’s multitude of media appearances. I’d found his TED Talk on CoffeeShop and watched it seven times. I’d scoured his Fiver feed with a fine-tooth comb and listened to all forty-eight of his podcast appearances. Each time, the constant duplicity had left me stunned. Over and over again, Gavin would describe his impoverished childhood and his dramatic hustle to the top, but leave out the part where his dad was best friends with a billionaire. He’d explain the national, state, and local trends that caused him to lose the mayor’s race in 2003, but somehow manage to omit the words “adultery” and “alcoholism”.

I’ve felt the same way as this interview has progressed. When Gavin recalled the way in which his bold, singular vision saved PlumpJack from collapse, he seemed to forget that between 2004 and 2005, Gordon Getty’s share of the company leapt from 49% to 85% (a fact that I gleaned from state records). When he told me the story of his incredible success as a venture capitalist, he neglected to mention that he’d started investing at the best possible time: right after the In-Q-Tel scandal, when Washington and Wall Street were running scared from tech stocks and every startup in Silicon Valley was desperate for cash. This whole time, I’ve been scrutinizing Gavin’s words, trying to sniff out the lies and burrow through to the man inside.

But, as I watch him close his eyes, breathe in deep, and savor the bouquet of a wine that’s about as complex as an IKEA desk chair, it suddenly hits me: there is no man inside. With Gavin, what you see is what you get. He really, truly believes that fancy mission statements are the key to fine viticulture, and he really, truly believes that he rose up from poverty through nothing else but his own hard work and ingenuity. The story he tells isn’t a carefully-crafted web of deception—to him, it’s as real as the nose on his face.

P.J. O’Rourke once said that politicians lie as easily as they breathe. If that’s true, then Gavin Newsom would be a terrible politician. A good liar has to know that he’s lying; if he doesn’t, then at some point, the truth will come out of nowhere and hit him like a freight train. If Gavin woke up one morning and decided to run for office again, the press would pick him apart until nothing remained but an empty vest. But in the ivory tower that is venture capital, Gavin can tell himself whatever fairytale he wants. As long as the money keeps flowing, no one will ever burst his bubble.

Satisfied with the bouquet, Gavin smiles. “Bottoms up!” He cheers, and we clink glasses. I raise mine to my lips. After all, there’s no sense wasting good Kool-Aid.

Brilliant! I don't know if the politics of this TL are better than others, but I would pay good money to see Timothy Olyphant in a revival of Have Gun Will Travel.
 
After reading Booker's chapter, I did not think you could top it. And then today happened -- I love how in the Newsom chapter there's less affection for the subject from our in-character author than in others. I think why Booker and Newsom stand out to me is capturing something real about their personalities in a totally different context.

Very excited for tomorrow -- and devastated we only have two left.
 
I love the way you really are trying to add character to these guys I really see how Gaven Newson has for instance turned to some of his worst habits now that he has all the money in the world and is just letting them run wild.

Also the part where Newsom uses the Tharinos tech for making wine was so funny and unique.
 
2003
October 25, 2024

I think that all of us, at one point or another, have found ourselves in a waiting room so empty and dull that we forgot what it was we were waiting for. Growing up, I used to dread the dentist’s office not for the needles or the drills but for the reception room, which was a frigid, black hole that sucked in youthful joy and crushed it like a cockroach. The walls were grayer than gray, the only thing to read was a technical manual on periodontal probes, and the fish in the tank looked suicidal. By the time I got into the chair, I’d be begging for a root canal just so that I could feel something again.

This is not that kind of waiting room. The walls are pastel pink, and the fish look like they’re on cocaine. There’s reading material everywhere, from the Bible-verse posters (“‘To all those who have, more will be given, and they shall have in abundance’—Matt. 25:29”), to the stack of get-rich-quick books on the table, to the mail-order catalogue selling bubblegum incense and platinum-plated prayer beads. I look down and glimpse the title of the catalogue: FreedomGear Product Guide, 2024.

If the name of that company rings a bell, it’s probably because someone you know has signed up to hawk its wares. You see, FreedomGear is what you might call a multi-level marketing firm, or MLM. It employs no full-time salespeople; instead, it has more than 200,000 “Freedom Rangers” who buy the product wholesale and try their best to sell it at a profit. The company bills itself as an easy path to riches, yet most of its distributors end up so grindingly broke that they start begging everyone around them for business. If you’re Plaxolinked with a Freedom Ranger (a distant cousin, say, or an old high school friend), chances are they’ve flooded your inbox with frantic, frenzied messages, desperately trying to convince you to spend thirty-eight dollars on an action figure of John the Baptist or a pink, plastic crucifix that doubles as a hairbrush.

My fifth star just so happens to be the CEO of FreedomGear, and his ghostly presence haunts this room. His portrait smolders down from the wall like the hero in a spaghetti Western, complete with leather boots, folded arms, and a manly sprinkling of five o’clock shadow. His drawling, nasally voice rings out from the corner, where a TV plays footage from a speech he gave at a FreedomGear conference last year: “excuses are the currency that allows you not to act!” He shouts. “Stop hanging around people who don’t want to win. Open your heart and find riches in Christ!” Offscreen, a raucous crowd cheers his every word.

I look up at the clock. He must be a very busy man—our appointment was at two, and it’s two-twenty-three. I sigh, lean back, and press my spine into the couch. Tilting my head, I spot a hardcover book sitting on the table beside me. I pick up the book, plunk it into my lap, and stare down at the cover. Time mucks down to the pace of cold molasses as my fingers inch closer and closer to the book, almost against their own will. Finally, I open it up and see the title stamped neatly across the cover page. Faith, Sweat, Tears, Success: The Personal Memoirs of Rafael Edward Cruz.

The memoirist begins with a dramatic account of his birth: “I was born on the prairie one cold, December night with the promise of America beating soundly in my heart.” Never mind that the prairie in question was Canadian (he was born just outside of Calgary). His Cuban father worked in the oil industry, and so the author spent the first few years of his life being whisked back and forth across petroleum-rich corners of North America. It wasn’t until he was four that the family found a permanent home, finally settling down in Houston in 1974.

His childhood was not a jolly one. “Felito,” as the young boy called himself, was lanky and thin with coke-bottle glasses, which led to constant bullying and teasing. “Eventually,” he writes, “I decided I’d had enough of being the unpopular nerd.” So, he ditched the glasses, took up sports, and swapped his funny-sounding nickname for the more esteemed and illustrious “Ted”. By high school, he’d been elected class president. “It taught me something incredibly valuable,” Ted writes of the experience: “with hard work, dedication, and an unbreakable faith in Christ, anything and everything is possible.” Between the lines, I spot another little Aesop: change your personality, gain the trust of those around you. Both lessons have served Ted remarkably well across the years.

Glasses or no glasses, young Ted’s brilliance was undeniable. He went from high school straight to Princeton and from there to Harvard Law, where he won medals in debate and honed a purist, conservative worldview shaped by Ayn Rand and Milton Friedman. Ted graduated in 1995 and took on several prestigious clerkships (including one for then-Chief Justice William Rehnquist) before moving back to Texas to join a law firm rich with political connections. Within two years, he’d gotten in good with every influential Republican in the state, and when then-Governor George W. Bush launched a presidential bid in 1999, Ted was brought on as a senior adviser.

“I advised Governor Bush on all things legal,” Ted writes in Chapter 4. “Immigration, crime, policy reform, all of it was my domain.” If that’s true, I don’t believe it. George W. Bush was a so-called “compassionate conservative” with neither the fire of Rick Santorum nor the brimstone of Mike Huckabee. By later standards, he was downright centrist, expressing sympathy for illegal immigrants and objecting to gay marriage purely on constitutional grounds. It boggles me to think that a moderate like Bush would have taken advice from a firebrand like Ted, but an old colleague who covered the campaign has assured me that it’s the truth (apparently, Ted was so natural in the role of the gray, humorless confidant that the backslapping Bush started calling him “Theodore”).

That stoic, unflappable façade lasted until 2 A.M. on election night, when the race was called for Al Gore. Then, all of a sudden, Ted turned into a pit bull. Within hours, he was live on Fox News, forcefully insisting that Gore’s three-thousand-vote lead in Florida was nothing but a Democrat lie. For the next two weeks, Ted led an aggressive, sweeping charge to overturn the results, filing endless briefs in federal court and appearing on TV night after night to demand a recount. When Bush finally conceded in mid-December, Ted felt completely and utterly betrayed. “Millions of Americans put their trust in Governor Bush,” Ted recalls on page 62, “and he sold us down the river. He promised to be a fighter, but he chickened out the minute things got rough.” While other Bush advisors moved on from the loss, Ted spent weeks ping-ponging back and forth across the right-wing media ecosystem, spouting dubious claims of fraud and scorching the Governor as a weak-willed, spineless turncoat. His fiery words whipped millions of conservative minds into a red-hot, roaring frenzy, and before long, he would wield it to his advantage.

In 2001, President Gore tapped Congressman Chet Edwards, a Democrat from central Texas, to serve as Secretary of Veterans’ Affairs. Edwards promptly resigned from the House, triggering a special election for his seat. Within days, Ted had sold his Austin loft, moved 100 miles away to Waco, and declared himself a candidate for Congress. He had no prior links to the area, and his vendetta against Bush had ruffled many a feather in the state GOP. But Ted’s media blitz had won the hearts of the region’s disaffected conservatives, and he snatched up the nomination and trounced his Democrat opponent in what he spins as a solemn, public service. “I had no choice but to run,” he confesses on page 72. “Since November, I’d met hundreds of faithful, hardworking Texans who felt they no longer had a voice in the affairs of their government. If I’d passed up a chance to give them that voice, I never could have lived with myself.”

In May of 2001, Ted stormed into Congress with the power of celebrity on his side. His youth, passion, and fiery eloquence brought him constant attention from the media, and within months, he was one of the loudest and most salient right-wing voices in America. The following year, Congressman Cruz thundered his way to a full, two-year term, by which point top conservatives were hyping him up as a future governor or senator. He practically volunteered himself for Rising Stars, and he made a natural addition to my list (by that time, even I was starting to realize that strong emotions, not strong ideas, were the wave of the future).

Our interview took place on New Year’s Day 2003 at a pulled pork joint in downtown Waco. Ted showed up in a ten-gallon hat and cowboy boots and answered all of my questions with his face buried in barbecue sauce. What had pushed him into politics, I asked? “The people of Texas,” he answered with a mouth full of meat, “and prayer. Lots of prayer.” How did he define conservatism? “No handouts, period,” he responded, licking honey mustard off his fingertips, “oh, and God first. God’s always first.” What was the future of the Republican Party? “Less talk, more fight,” he replied, picking gristle out of his teeth with an unclipped fingernail.

In many ways, Ted was years ahead of his time. For the GOP of the early 2000s, his views on conservatism were radical and new, and he did not hesitate to make them known. In the wake of 2/12, for example, most Republicans supported Al Gore’s push for a Department of Science and Technology, believing that it would enhance national security. But Ted became the new agency’s fiercest enemy in Congress, contemptuously tarring its billion-dollar contracts with Silicon Valley as “welfare for big tech babies”. Later on, while nearly every prominent Republican was calling for Saddam Hussein’s head on a plate, Ted went on Fox News to decry the War in Iraq as a worthless, foreign entanglement. He was developing themes that would dominate right-wing discourse in the years to come: isolationism, disdain for bureaucracy both public and private, and a raw, unvarnished hatred of anything that could be called “the establishment”.

But while Ted’s acid tongue was the source of his power, it was also his fatal flaw. He was known to unleash torrents of rage against anyone he disagreed with, even if (especially if) they were members of his party. Ted was so friendless on the Hill, one Republican joked that “if you killed Ted Cruz on the floor of the House, and the trial was in the House, nobody would convict you.”

Still, Ted’s love affair with the right-wing media shielded him from consequence—until, that is, he picked a fight with the wrong guy. Congressman Tom DeLay of Texas had first landed in Washington in 1985 as a radical, bomb-throwing outsider, but after eighteen years in the House, he was a party man through and through, having clawed his way up to senior leadership. Ted loathed DeLay, though sources differ as to why—on page 124, Ted himself makes it a matter of principle, calling DeLay’s resistance to pulling troops from Afghanistan “utterly unconscionable,” but the Washington Post framed it as a simple clash of egos, reporting that the rift had begun when Ted was denied a prized committee assignment.

Either way, by the time Ted returned to Washington in early 2003, Republicans had lost control of the House, and then-Speaker Dennis Hastert had resigned from party leadership. In the ensuing shakeup, Ted adamantly refused to endorse DeLay’s bid for Minority Leader. When asked why in a live Fox interview, Ted exploded into a three-minute spew of bilious, spiteful rage. “I cannot support Tom DeLay,” he declared, “because Tom DeLay is a man with no values, no morals, and no convictions. In the short time I’ve known him, I have never seen him act in anything but his own self-interest. He’d set fire to an orphanage if it brought him more power.”

Instantly, Ted’s rant became the stuff of legend. It saturated the news cycle for weeks, and later that year, when CoffeeShop was first launched, it became the first news clip ever to reach 100,000 sips. Never mind that Ted’s claims were categorically false (Tom DeLay most certainly did have convictions, many of which were in line with Ted’s own). Ted was playing the long game. He could sense that his wing of the party was in the ascendant, and by burning his bridges with the establishment, he’d be a shoo-in for House leadership once the hardliners finally took over. All he’d have to do was hang on to his seat and wait.

And, in a way, Ted was right—within ten years, many of his views would become mainstream planks of the Republican platform. What Ted had failed to foresee was that the Earth would drop out from under him. For Tom DeLay, after all, was a Texan, and his pull in state politics surpassed that of any other federal politician. So Ted had no right to be shocked when, in July of 2003, the state legislature redrew his district to include several sapphire-blue sections of Austin, making it perilous ground for a firebrand like himself. Ted still filed for re-election, but found to his horror that his powerful friends had turned their backs, his big-check donors had stopped answering the phone, and a primary challenger had emerged seemingly out of thin air. Ted had displeased the powers that be, and when primary day rolled around, he lost renomination by more than ten thousand votes.

The loss left Ted demoralized and dejected. “I was as aimless as Hagar wandering the desert,” he writes on page 154, “so I called out for guidance, and God set me straight.” Item one on the divine to-do list: marriage. Ted and his fiancée, Heidi, had put it off for so long that she’d threatened to break off the engagement, so they finally tied the knot in early 2005, just two weeks after his departure from Congress.

Next up was a new job, which Ted found, of all places, in Michigan, at the offices of the multi-level marketing juggernaut Amway. Then as now, Amway was extremely controversial. It promised its distributors an easy path to success, but the only sure way for them to make money was to recruit other distributors. To its enemies, Amway was nothing but a glorified pyramid scheme. For Ted, though, it harkened back to a simpler, purer time in American history, to an age of rugged pioneers and hardy yeoman farmers who survived on nothing else but their own hard work and ingenuity. In a world overrun by corporate tyrants and petty government elites, Ted reckoned, Amway was a swashbuckling hero, turning establishment slaves into rough-riding entrepreneurs and breathing new life into the American Dream.

Amway’s billionaire CEO, Dick DeVos, had been one of Ted’s biggest campaign donors. When Ted lost his seat, DeVos gave him a plum position in the office of Amway’s chief counsel, where the young ex-politician worked wonders. In 2006, the FTC launched an investigation into Amway’s business practices. Instantly, Ted counter-sued and used the media to spread his outrage, loading his words with colorful hyperbole: The federal government, he charged in one appearance on The O’Reilly Factor, was “The Tyrannical Hulk,” while Al Gore was “Godzilla on steroids.” Soon, every talk radio host from Maine to Modesto was parroting Ted’s points. With the help of Ted’s silver tongue, Amway triumphed in court and prevailed on appeal, stoking outrage among liberals. The Supreme Court finally took up the case in 2008, by which point support for Amway and its business model had been woven into the fabric of American conservatism. Not even the Garland Court’s thin, liberal majority could squirm free of Ted’s cunning, legal arguments, and, in one of its most contentious opinions so far this century, the Court ruled five-to-four that multi-level marketing was technically—that is, totally—legal.

Amway v. FTC unleashed an avalanche. Before the ruling, multi-level marketing firms made up only a tiny section of the economy, their product lines mostly confined to nutritional supplements and hair-loss pills. After the ruling, MLMs sprung up like weeds around every conceivable industry. These days, just about anything—books, insurance, sushi, chemotherapy—can be bought from an MLM, and according to the Department of Labor, as many as twelve million Americans work at least part-time as MLM distributors.

Not long after the Court’s decision, Ted left Amway for greener pastures. He could have easily gotten back into politics; Ted’s patron, Dick DeVos, was now the Governor of Michigan, and the stances that had made him a wingnut five years prior had gone mainstream (for one thing, the In-Q-Tel scandal proved that the CIA really had been paying tech firms to pump out new surveillance equipment). But Ted had lost interest in public service. Instead, in 2011, he founded FreedomGear, which quickly blew past its competitors to become one of America’s largest MLMs. Ted’s industry know-how certainly helped, but perhaps even more crucial to FreedomGear’s rise was the religious angle: during his time at Amway, Ted had noticed that the most successful MLMs are those that pluck at their distributors’ spiritual heartstrings. So, instead of makeup kits or summer dresses, FreedomGear deals in trinkets, knick-knacks, doodads, and tchotchkes, all with a light sprinkling of Jesus. Best-selling items include a corkscrew that plays “O Come, All Ye Faithful,” and a mug on which is printed the so-called Eleventh Commandment: “THOU SHALT NOT TALK TO ME BEFORE I’VE HAD MY COFFEE.”

Since its founding, FreedomGear has been under near-constant scrutiny. In 2013, an investigation by the Christian Science Monitor revealed that 60% of FreedomGear distributors end up thousands of dollars in debt, and almost none of them succeed in turning a profit. Since 2017, the Feds have sued FreedomGear for everything but its business plan, including tax fraud, wage theft, and lead paint in its children’s toys. Through every scandal, Ted has sought cover in his spirituality. In 2019, when OSHA arrived to shut down a FreedomGear warehouse in Fort Worth, Ted stood in the doorway like a bearded George Wallace and cried out to the skies for a miracle. Last year, when three FreedomGear vice presidents stepped down on charges of embezzlement, Ted tarred the SEC as “King Herod’s agents,” and beseeched the FreedomGear faithful for prayers and donations.

At times, Ted’s piety muddles the line between businessman and preacher. Before, Ted’s Christian faith was but a small part of his brand, like background music to his free-market soliloquies. Now, it’s his entire persona. In his posts on the company Plaxo page, Ted pulls liberally from the Bible (“in the Book of Isaiah, God tells us that he declares new things before they happen. So, here’s a sneak peek at our new line of Ash Wednesday neckties!”). At FreedomGear summits, Ted comes off less like Scott McNealy and more like Joel Osteen (during his keynote address last year, one attendee had to be hauled out on a stretcher after she collapsed to the floor and started speaking in tongues). In the closing chapter of his memoir, Ted reflects on his transformation from hard-nosed lawyer to Evangelical guru: “my faith has enriched my life so deeply, I can’t even fathom who I was before I discovered it. Once, I was obsessed with worldly ambition. I would go to war with other men over the tiniest specks of power. But once you’ve let the light of Christ into your heart, politics feels like patty cake.”

The introspective turn catches me off-guard. A question comes together in my mind: after 223 pages of self-serving bravado, has Ted finally owned up to a personal flaw? In the twenty-two years since we last spoke, did he somehow develop the capacity for self-awareness? I think back to my trip to Napa last month, where I showed up to confront a liar only to find that there were no lies. What if Ted’s story is the same? What if his skyward turn was a genuine journey of faith? What if his endless Jesus talk reflects a true, inner communion with the divine?

Just then, above me, I hear footsteps. I look up at the staircase and see my fifth star in the flesh, descending from on high like an angel. I steal one last glance at my watch: 4:37. Two-and-a-half hours late. I’ve read a whole book in the time it took Ted to show up for our appointment.

He steps off the stairs looking precisely as he does in his portrait, right down to the stubble on his chin. I expect an invitation upstairs; instead, I get a clammy handshake, a mumbled apology, and a nonchalant, easy grin. He plops down across from me, and I pull out my list of questions. I start rattling them off, but his answers float in and out of my mind like wispy cottonwood (after all, I just read his life story from cover to cover—why bother paying attention?)

I watch Ted’s face just closely enough to see that he, too, is utterly disconnected. His pupils are glassy and dull, he leans back into the plush-covered chair like he’s settling down for a nap, and even his whiskers seem saggy and bored. I’m starting to wonder if he even remembers who I am. Then, out of nowhere, he lights up like a halogen bulb. “You know,” Ted says, leaning forward in a sly, don’t-spill-my-secret kind of way, “you strike me as pretty ambitious. How much do you make in a month?”

My jaw falls open. All of my words desert me.

From a hidden pocket, Ted pulls a neat, folded brochure: How to Become a FreedomGear Ranger. “If you distribute for us,” he continues in a soft, fluid drawl, “You can double your income. Maybe triple it. We had this one woman in Idaho. When she started out, she had thirty-four dollars in the bank. Eight months later, she bought a Ferrari.”

The brochure dangles below my nose. An unseen force compels me to grab it, if only to get it out of my sight.

Ted nods his head in approval. “Give it some thought,” he says, rising from his seat with a wide, Texan grin. “When you’re ready…” he smiles, sticks out his thumb and pinkie, and raises them to his ear like a telephone receiver. “You know how to reach me.” Then, he winks, turns, makes his way over to the staircase and ascends to a higher plane, cowboy boots clopping crisply on every step.

The room falls silent. My jaw hangs open like a Christmas nutcracker. The awareness sets in: to Ted, I’m not a journalist, a writer, an interviewer, or anyone of particular importance. I doubt he even remembers my name. To Ted, I’m just another dollar sign, another hapless sucker waiting to be bilked.

I look up once more at the portrait on the wall. Ted’s scruffy mug glowers back, squinting down like Clint Eastwood in A Fistful of Dollars. The cowboy schtick is a paper-thin illusion (if Ted has ever roped a steer or tied a hog in his life, he left it out of his memoir). But his powers of deception are not to be underestimated. Ted’s boundless greed is plain as day, and yet, for one fleeting moment, I truly thought he’d seen the light—or at least enough of it that his love of the Almighty might trump his love of the Almighty dollar. I was completely and utterly fooled.

I rise from my seat and make my way over to the door. The brochure is still in my hand; I raise my arm to flick it into the trash. Mid-toss, however, I pause. After a moment’s reflection, I fold up the brochure and slide it into my back pocket. Now, if I’m ever struck by the sudden urge to piddle away my entire life savings on “GOD IS RAD” T-shirts or manna-flavored protein bars, I’ll know exactly who to call.

2003 Cruz Framed NTB (1).png
 
Last edited:

Indiana Beach Crow

Monthly Donor
Morbid curiosity seizes control of my hand. I watch, detached from my body, as Gavin pricks my thumb, squeezes a droplet of blood into a tiny, plastic tray, and feeds it into the machine. He does the same to his own thumb, then flips a switch. The machine whirs, then whines, then whizzes. After a minute, it dings, and a button lights up which reads Drink.​
Gavin Newsom actually found a way to turn Elizabeth Holmes's scam into something slightly useful.
 
Top