AHC: Barack the Harold: Obama as Mayor of Chicago

Exactly what it says on the tin. The challenge here, if you choose to accept it, is to make the incumbent President of the United States, Barack Obama, the Mayor of Chicago in some alternate timeline. The only caveat is that the divergence has to come after Obama's victory in the 2004 Senate race. Good luck.
 
Exactly what it says on the tin. The challenge here, if you choose to accept it, is to make the incumbent President of the United States, Barack Obama, the Mayor of Chicago in some alternate timeline. The only caveat is that the divergence has to come after Obama's victory in the 2004 Senate race. Good luck.

Obama loses to HRC in 2008 primaries then runs for mayor in 2011 because he's tired of the Senate.
 
Obama loses to HRC in 2008 primaries then runs for mayor in 2011 because he's tired of the Senate.

Ah yes, that seems to be the obvious point of divergence, but you're forgetting one big problem, Jesse Jackson Jr. Jackson had been waiting for a very, very long time to run for Mayor, and everybody knew it. The only reason he didn't run when his chance finally came, is that he was tainted by scandal, a scandal that wouldn't exist here. If Obama is still in the Senate, the Governor isn't going to be trying to sell the seat, because the seat selling scandal doesn't happen, Jackson by definition isn't implicated in it, and therefore, he's still a viable candidate in the race for Mayor when Daley retires. So the question is, how do we avoid a higher profile version of 1989? That is, either you have to say why Obama wins despite the Jackson candidacy, or you have to prevent him from entering. Jesse Jackson Jr. is the main obstacle to Mayor Barack Obama in my opinion.
 
Presuming we can find a solution to the Jesse Jackson Jr. problem, I wonder if a more interesting option might be 2007. Let's say Daley decides to retire then, let's say his Olympic Plans never really get off the ground, this leaves the Democratic Primary in 2007 wide open. Obama would have had a choice to make in 2007. Again, assuming we can deal with Jackson, and he can avoid the Sawyer-Evers trap, a run for Mayor then might look tempting for Obama. But running for Mayor means that he probably can't run for President in 2008. So the question is, would he have run for the Mayor of Chicago, an election he has a good chance of winning, or stay run for President, and conceivably, lose to the prohibitive front-runner, Hillary Clinton?
 
Obama wanted to be Mayor of Chicago someday. Check.
By 2004, Obama is more important to Illinois than Jesse Jackson Jr. Check.

Just have him lose the primaries in 2008. Although he might go for Governor in 2010.
 
State Senator Obama goes harder after Chicago corruption, either becoming a hero (with a political future) or a martyr.
 
After a second term as President Barack Obama retires, dedicating his life to getting Chicago the Summer Olympics. Finally he gets the city approved for the 2024 Olympic Bid, with Mayor Emanuel retiring Obama decides to run for Mayor and sees the city through the Olympics before finally leaving politics to hit the lecture circuit.

Improbable, but the only alternative to a 2007 POD
 
Obama would have larger support then Jesse Jackson and would probably win the the younger African-American vote compared to the older African Americans who sympathize with the Jesse Jacklson name sake. Rahm Emmanuel would probably still be a congressmen and would make a run but I think overall Obama would win.

Something along the lines of...

Barack Obama 45%
Rahm Emmanuel 31%
Jesse Jackson Jr. 20%
Other 13%
 
Well, the problem with Obama vs. Jackson is the 1989 problem. Regardless of Obama's national standing, of his popularity within the stat at large, Obama vs. Jackson means that the African American vote in the city is divided. So, the question is, can Obama do well enough elsewhere to make up for that divide? Or is the division doomed to allow for the election of someone like Gary Chico?
 
Well, the problem with Obama vs. Jackson is the 1989 problem. Regardless of Obama's national standing, of his popularity within the stat at large, Obama vs. Jackson means that the African American vote in the city is divided. So, the question is, can Obama do well enough elsewhere to make up for that divide? Or is the division doomed to allow for the election of someone like Gary Chico?
Yes. Obama will get the white liberal vote and the majority of the black vote. He will probably win by 60% or more.
 
Yes. Obama will get the white liberal vote and the majority of the black vote. He will probably win by 60% or more.

What makes you so confident of that? After all, Jackson had been preparing for this for a much longer time than Obama would have been. And we all know how important preparation is in politics.
 
What makes you so confident of that? After all, Jackson had been preparing for this for a much longer time than Obama would have been. And we all know how important preparation is in politics.
I'd recommend skimming Young Mr. Obama, which details Obama's rise in Chicago. He had white liberals behind him 100%. Blacks were more suspicious, but by 2004, he was "the one," definitely more attractive than Jesse Jackson Jr.

It's pretty unlikely that Jackson even runs if Obama declares that he's going to run.

After a second term as President Barack Obama retires, dedicating his life to getting Chicago the Summer Olympics. Finally he gets the city approved for the 2024 Olympic Bid, with Mayor Emanuel retiring Obama decides to run for Mayor and sees the city through the Olympics before finally leaving politics to hit the lecture circuit.

Improbable, but the only alternative to a 2007 POD

In 2019 he'll only be 58. It could happen.
 
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Depending on how exactly you mean the wording of the OP, if you accept a 2004 POD that makes Obama Senator but ot president, the key is Obama' keynote in Boston. Either a no performance or poor performance could do in the 2008 run.

This article detailing the Speech gives some good PODs.

For a no performance, it's simple. Jennifer Granholm or another speaker gets it for one of a variety of reasons. (Telling The Atlantic Monthly, "Sometimes Kerry just doesn't have that oomph." for example.)

A less likely possibility is having the state budget fight go on a few more days.

For a poor performance there are several possibilities:
Obama's a breakfast or lunch can disagree with him. According the above article, breakfast was an omlette and lunch was a turkey sandwich, and either could cause food poisoning fairly easily.

Obama had trouble adjusting his speaking style.

Adding to the tension in Boston was Obama's rough start at rehearsals. ... Obama, who prefers speaking extemporaneously, had no experience working with a teleprompter or addressing a group this loud and lively. ... Obama struggled early on to master the mechanics of this new speaking environment. First, he had to train himself to read the words off the teleprompter screens without having it look or sound as if he were reading. He also had to adjust his speaking style.

If he doesn't get all that down, he'd do poorly.

Also, he was giving so many interviews that he was starting to lose his voice.

Gibbs recalls that by midafternoon, Obama's voice was getting hoarse from overuse. In the middle of one taping, Gibbs had to search the FleetCenter for hot tea and lemons to help soothe Obama's throat. "I can remember having this panic attack," he says: "Oh, my God, what if he's written this tremendous speech and everything's great, except I've scheduled too many TV interviews and he loses his voice?"

Finally, if you watched The Speech, you may remember he had some trouble hitting his stride at the start. If he didn't it wouldn't have been nearly as effective.

So, for a really awful performance, throw those three together, and Obama bombs the Keynote. Add in the tensions with Kerry's "stealing" his best line, and you can put off 2008.

Of the remaining possible 2008 DP candidates, Kerry and Gore remain damaged goods, Clinton has too much baggage from her husband's term, Edwards has the scandal, Richardson had potential scandals, Gravel was going Green, and Kucinich is unliklely to win the natuional race. That leaves Biden, Dodd, Vilsack, Bayh, and probably Mark Warner, and my insinct goes to Bayh.

Meanwhile, Obama sees the writing on the wall in the 2010 and better opportunity back home, doesn't run for re-election, but instead runs for mayor in 2011. Then, after getting some executive experience, he runs for the presidency in either 2016 or 2020.
 
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