Wilson was a nobody in 1908. Hell, he was barely anybody in 1912. He didn't enter politics until 1910 when he ran for Governor of New Jersey.
Wilson was
not a nobody in 1908, though he had not held electoral office. He had received lots of publicity as president of Princeton (not the sort of post a Democrat usually held) especially for the Quadrangle Plan which was portrayed as a "democratic" assault on the "aristocratic," "snobbish" eating clubs. Conservative businessmen like George Harvey, the very wealthy owner of the *North American Review* and *Harper's Weekly* boosted him, and (at Harvey's suggestion) Joseph Pulitzer included him on his *New York World* list of sixteen Democrats who would be preferable to Bryan (the list was called "sixteen to one" in a dig at Bryan's past advocacy of free silver). As I noted at
https://www.alternatehistory.com/fo...nate-wilson-in-1908-and-bryan-in-1912.299615/ "The combination of political conservative and educational reformer, Harvey thought, would be attractive to the public."
As I also note in that post,
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with respect to Wilson not holding any public office, one has to remember that not very many Democrats outside the South *did* hold major public offices at that time. As a Southerner who lived in New Jersey, Harvey argued, Wilson had a chance of carrying New Jersey and New York, states that he thought essential to a Democratic victory. (Had not Bryan proven the futility of looking for a southern-western alliance instead? Ironically, Wilson himself was to vindicate a modified "Bryanite" strategy in 1916 as Truman was to do in 1948--in both elections, the Democrats, with support from western farmers and with enough backing from trade unionists to win one or two key midwestern states Bryan had lost, prevailed despite losing New York and New Jersey. But Harvey was, psychologically, still living in the world of Samuel Tilden and Grover Cleveland--the only two Democrats to win the popular vote between 1856 and 1912--who relied on a South-Northeast alliance.)
There was of course one thing wrong with this reasoning. The Democrats were not in the least in the mood to nominate a conservative in 1908. They had tried that with Parker in 1904 and had been defeated even worse than when they had twice nominated Bryan.
So what is necessary to give Wilson any real prospect of winning the nomination in 1908? IMO it is this: instead of nominating Parker, the Democrats have to try "radicalism" yet a third time in 1904 (presumably this time with Hearst instead of Bryan) and go down to crushing defeat. Instead of blaming it on Hearst's dubious moral reputation or on TR's personal popularity or on the prosperity the country was enjoying, they will conclude that radicalism is the source of all the party's ills, and that only with a conservative do they have any chance in 1908...
Anyway, I think we can fairly assume that Wilson will lose to Taft in 1908--Taft being the choice of the popular TR, and the nation enjoying peace and prosperity. Moreover, the Democrats will be badly divided; Taft might not be particularly attracitve to progressive Democrats, but some might stay home, Hearst might try a third party candidacy, and even if he doesn't, Debs is available as a protest vote for the most radical Democrats.
So what happens in 1912? I think this is Bryan's best chance to win not only the nomination but the presidency (assuming that we still get the Taft-TR split). He can point out that after all in 1896 and 1900 he did better than either of his successor candidates (Hearst and Wilson) and that the Wilson campaign in particular showed the folly of the Democrats trying to attract conservatives.