Challenge: President Upton Sinclair in 1921.

Timeline-191 did this, but you know all the criticism and its somewhat implausible.

The challenge here is to have Upton Sinclair be plausibly elected to the Presidency in 1920, with a PoD after 1900 if possible. As a Socialist if you can.
 
The Progressives don't collapse after losing in 1912. President Wilson goes to war with Germany in 1915 after the Lusitania is sunk. The Progressives try to draft Theodore Roosevelt to run again in 1916, and he reluctantly agrees after being refused by the Republicans. An electoral deadlock occurs, so the election goes to the House, which reelects Wilson. The post-war recession happens again, and communism becomes more popular than it was IOTL due to America being in the war longer. Roosevelt has died, so the Progressives nominate Robert LaFollette...who loses. However, after four years under a conservative Republican administration(possibly Warren Harding), the progressive factions of both the Democrats and Republicans, as well as many populist groups throughout the nation, turn to the Progressives in 1924, and young and charismatic Upton Sinclair is nominated, after two terms in the House of Representatives. He wins.


I know it's not exactly what you asked for, and I don't how plausible it is, but it's what I came up with.
 
I am totally convinced that there is no way any Progressive, or especially socialist, gets elected after WW1. It is impossible. The Progressives pissed of the US public with their anti-free speech laws and drastic economic measures and there is good reason the Republicans won in a historic landslide in 1920. If you look at voting records of non-Progressive Republicans, they voted universally against the Sedition Act of 1918 and clearly drew a line in the sand in opposition of the Executive overreaches during the war.

So, in order to fulfill this "challenge" we need something very big and weird to happen, such as German victory in WW1 and quickly. Have Wilson not make the Fed Reserve and essentially back-stab the Progressives. Have the next President be a reactionary, anti-immigrant Republican. Have him get elected due to Teddy running again and splitting votes with Wilson. I would have to read up on names again to see who was out there like that in 1916.

Then, in the wake of a terrible pandemic and a swing towards hard Progressivism, have Upton SInclair become the new standard bearer of a US version of a social democrat. For this to occur, Sinclair would have had to sold out his beliefs for about ten years and enter politics, perhaps being one of the first senators "directly elected."

Sinclair then can win in 1920 or 1924. We would need even more fantastical PODs to make Sinclair President during the Great Depression.
 
Robert La Follette was one of the biggest voices against Wilson/Palmer's tactics and he was essentially the Progressive standard bearer after TR's death. Big difference between western/eastern Progressives...

Sinclair actually bolted from the Socialists because of their coming out against the war effort.
 
The Progressives don't collapse after losing in 1912. President Wilson goes to war with Germany in 1915 after the Lusitania is sunk. The Progressives try to draft Theodore Roosevelt to run again in 1916, and he reluctantly agrees after being refused by the Republicans. An electoral deadlock occurs, so the election goes to the House, which reelects Wilson. The post-war recession happens again, and communism becomes more popular than it was IOTL due to America being in the war longer. Roosevelt has died, so the Progressives nominate Robert LaFollette...who loses. However, after four years under a conservative Republican administration(possibly Warren Harding), the progressive factions of both the Democrats and Republicans, as well as many populist groups throughout the nation, turn to the Progressives in 1924, and young and charismatic Upton Sinclair is nominated, after two terms in the House of Representatives. He wins.


I know it's not exactly what you asked for, and I don't how plausible it is, but it's what I came up with.

I think that it would take a lot to convince the American people to go back to progressivism after the war. I do think it could be done though (I should get back to writing my own TL). I'm not sure if it would be possible to get someone as radical as Upton Sinclair, however.
 
You would need a more Bourbon Wilson in the 1910s. Or a complete collapse of the GOP in twenty years leading to a mass Socialist Party...led by a guy that was apparently pro-WWI. I don't see it.
 
Have Upton Sinclair Sr. not be an alcoholic and be successful in his liquor business, and mend relationships between Upton Sinclair and his mother Priscilla Harden Sinclair. That means he doesn't get disassociated from his more wealthier relatives and it means that the Sinclair family isn't ruined, nipping his socialist tendencies in the bud. When Sinclair actually goes into law school, have Sinclair actually stick to law, instead of writing pulp fiction. He gets recruited by some Wall Street business and becomes famous for that, as well as becoming a archconservative as well. Sometime in the late 1900s or the early 1910s Sinclair decides to run for Congress as a Republican and wins, serving as a congressman or a senator. In 1920, Sinclair is selected as the compromise candidate when the Republicans are deadlocked between Wood and Johnson, and easily defeat the Democratic candidate.

Edit: Now that I think about it, I might have killed a whole bunch of butterflies. Oh well.
 
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