Before he had his stroke (and after), Woodrow Wilson wanted to pursue a third term for the Presidency. Coming off of WWI and a decently successful eight years, would the party line up behind him if he doesn't have a stroke and runs again? I think that they would (they did it with Bryan however many times), and could he win? While the OTL election of 1920 wasn't close, with Wilson himself running the Republicans would probably not choose to run Harding against him. We might have one of our smartest Presidents running against one of our dumbest. But, without Harding's charisma and with a solid 8 years, I think the Dems can probably squeak out a win, especially if Marshall was dropped for someone else (maybe Cox?).
Assuming that Wilson somehow wins, a death in the office seems likely. I'd imagine that he would still have a stroke, probably early on, and the added weight of a campaign and the job might could push him to die in '22 or '23, after years of being essentially incapable. With Wilson dead, lets say that James Cox becomes President. What changes? How do the 1920s progress without being Republican dominated? Prohibition is probably likely, but is the Great Depression locked (probably)? What about into the 1930s? If Cox becomes President in 1923, he can run in '24 and in '28. If the Depression starts in any of those years, the Republicans gets to be the party to try and fix things, and have control of the White House for another 20 years probably.
Assuming that Wilson somehow wins, a death in the office seems likely. I'd imagine that he would still have a stroke, probably early on, and the added weight of a campaign and the job might could push him to die in '22 or '23, after years of being essentially incapable. With Wilson dead, lets say that James Cox becomes President. What changes? How do the 1920s progress without being Republican dominated? Prohibition is probably likely, but is the Great Depression locked (probably)? What about into the 1930s? If Cox becomes President in 1923, he can run in '24 and in '28. If the Depression starts in any of those years, the Republicans gets to be the party to try and fix things, and have control of the White House for another 20 years probably.