"...described the wedding almost in terms reserved for European dynasts; a caricature in the Sun even had Quentin decked out in the ceremonial uniform of the German Kaiser.
This was, perhaps, not far off the mark, for the nuptials joined together two of the most powerful families in the United States in a way that was perhaps unexpected. The Whitneys were about as much of genuine New York aristocracy as one could find; Flora's mother was, herself, an heir to the Vanderbilt fortune, and though the Whitneys were thought to lean Democratic, Flora's uncle William had married Helen Hay, daughter of the former President John Hay and bete noire of the young Roosevelt, and her aunt Pauline had married a British Tory peer and industrialist. It was thus a family with many fingers in many pies, their political allegiances much more fluid and pragmatic than that of the rock-ribbed Democratic clan of Oyster Bay, and also a family that could credibly look at a marriage to a Roosevelt and think it perhaps beneath Flora's station.
Theodore was under no illusions that Harry Payne Whitney approved of his daughter's choice in a beau, because Whitney had told him as much, to his face, at the Knickerbocker Club when Quentin had come to him shortly after the end of the war to ask his daughter's hand. Whitney was not heartless, though; an avid sportsman like Theodore with a particular interest in thoroughbred racing, he had been relieved that his son, Cornelius Vanderbilt Whitney, had not gone off to war and was currently spending a year as a desk clerk in the Army before attending Harvard, and he was moved by Theodore's loss of his two eldest sons and the wounds suffered by the two younger. Whitney clarified after this for Theodore, whom he respected personally even if he found his boundless energy and bullheaded nature quite tiring, that while he did not particularly approve of the match and wanted his daughter to take a yearslong grand tour of Europe before her engagement, he had told Quentin that he would not intervene to block a marriage, and that was good enough for the Roosevelts. The engagement had gone on, and so one of the grandest weddings in the history of New York was planned.
The political implications of the match were well understood, and not just because former President Hearst was on the invite list (former President Hughes, a close friend of the Whitney family despite political disagreements, was pointedly not). Theodore had, after all, not long ago been New York's hard-charging, disruptive Mayor, and one not particularly popular with many of the masters of the universe who nonetheless attended as a courtesy to the Whitneys; Helen Hay Whitney herself complimented the handsome groom and his gallantry in the war, but huffed "it is a shame he's the son of that horrible man!" Theodore, as was his wont, cared not a wit - his family had picked itself up from middle-class respectability [1] through his media empire to the upper echelons of American power, and now they were sealing their place within it as the Whitney and Vanderbilt fortunes were now as much part of the Roosevelt name as what he had made for himself with newspapers. The comparisons to a dynastic wedding in Europe was thus not unfounded, because newspapers reported it as much at the time - with the wedding, it suddenly became considered almost inevitable that Quentin would have a career in New York, and perhaps national, politics, an enormous amount of pressure to foist upon an affable young man of only twenty-one years of age.
The grand wedding at Oyster Bay had other effects, too; Roosevelt, a man for whom there was nothing quite like a good grudge, elected to further inflame his enemies within the New York Democratic Party by making Hearst an attendee whom he honored with a seat near the front, while declining to invite important figures like Al Smith, Bill Sulzer, or even Charlie Murphy, all three of whom Whitney did not care for but had felt pressured to invite to avoid a dust-up that would diminish his influence in Albany or at Gracie Mansion. The snub was understood as such and the factional rift amongst New York Democrats that had more to do with personality and generation than ideology deepened; Roosevelt did not know it yet, but he had earned powerful enemies for the remaining years of his life, and his influence was about to enter a very long period of decline as that of Smith in particular grew.
The reemergence of a glad-handing Hearst from two years of political semi-exile also served to open up a new wrinkle in the ex-President's personal life, one which quickly came to be a political liability just a month later as he attempted to launch his long-expected political comeback at the New York State Democratic Convention in Schenectady. For reasons that are still unclear, Hearst informed Roosevelt that well-liked former First Lady Millicent Hearst was unable to attend, creating a dubious excuse, and then privately made arrangements for his mistress Marion Davies - an actress in the employ of Roosevelt's Cosmopolitan Studios, a small outfit still at that time - to attend "as a guest of the Roosevelt family." Hearst's dalliances since leaving the Presidency with young Broadway starlets was something of an open secret in New York high society, but his intense personal privacy and a good deal of fear of the famously vindictive former President had kept such things quiet. Bringing Davies to the Roosevelt-Whitney wedding, on the other hand, put things almost entirely out in the open: Hearst and Millie were barely on speaking terms any more, and he was starting to live openly with his mistress. The Hearst-Davies relationship is a strange though oddly affectionate concluding chapter to the 27th President's life, especially once they absconded to California to live in a state of quiet opulence once he inherited the rest of his father's mining empire the following year, and it began in large part in late June 1918, when Davies had her "debut," if that was the term for it.
The wedding itself, of course, was just as much a spectacle as the press had hoped. Roosevelt arranged for a Navy boat to give a salute in view of Sagamore Hill (arranged by "cousin Franklin," startling the neighbors; doves and peacocks wandered galore, and there were bears and lions on site as well. Oriental performers brought from Chusan were the main entertainment of the evening, and Quentin and Flora left the grounds for their honeymoon in Europe under a sword salute of Quentin's fellow veterans, all of whom were men whom he had served with personally. Memories of that black Christmas two years earlier had entirely faded; the young couple, madly and deeply in love and with all the promise of the future ahead of them both romantically and professionally, stirred something in Theodore's heart he had almost forgotten was there. There were battles to come, in the tumultuous years after the war, a great many that he yearned to fight - but for one night, the Lion of Sagamore Hill could rest and look proudly upon the addition to his pride..." [2]
- American Royalty: The Roosevelt Dynasty's Enduring Legacy
[1] This may admittedly be underselling the earlier generations of Roosevelts a bit
[2] Lot going on in this chapter as we of course build towards the conclusion of the 1910s NY Dem contest between the Hearst-Roosevelt old guard and Smith's rising faction, as well as something of a generational transition as we finally get to one of the more wild features of Hearst's OTL life and Roosevelt nearing the end of the road (he won't die at the same time as OTL, but Teddy was a man who I think was destined to burn hot, bright, and fast). It's been interesting going back and re-reading content from the 1880s and 1890s and seeing how prominent the setup of the flipped-around Roosevelt and Hearst were even then, and it'll be weird when we eventually say goodbye to one and then both of them.