Roosevelt would be a leading Progressive. 1912, 1916, 1920. Any time a Democrat wins is an opportunity for TR.
 
Roosevelt would be a leading Progressive. 1912, 1916, 1920. Any time a Democrat wins is an opportunity for TR.

He would need to run for Governor again in order to be relevant by 1912.

To my knowledge, TR and Henry Cabot Lodge had planned on building up Roosevelt's political support from 1901-1904 in preparation for a run to succeed McKinley. McKinley didn't seem to have anything against TR, although the Old Guard did, and in fact he did nothing to prevent him from becoming VP in 1900. So it's possible that Roosevelt would be nominated in 1904, though that's far from guaranteed. Fairbanks is likely to be on the 1904 ticket, either as President or as VP.
 

manav95

Banned
He would need to run for Governor again in order to be relevant by 1912.

To my knowledge, TR and Henry Cabot Lodge had planned on building up Roosevelt's political support from 1901-1904 in preparation for a run to succeed McKinley. McKinley didn't seem to have anything against TR, although the Old Guard did, and in fact he did nothing to prevent him from becoming VP in 1900. So it's possible that Roosevelt would be nominated in 1904, though that's far from guaranteed. Fairbanks is likely to be on the 1904 ticket, either as President or as VP.

The 1904 Republican Convention becomes so deadlocked it only ends when Roosevelt challenges Fairbanks to an honorable duel with fists, because they're gentlemen. Fairbanks accepts and the boxing duel lasts 5 minutes. Theodore Roosevelt wins because he actually knows how to box and proceeds to win the nomination unanimoisun in this sheer display of mabliness. Fairbanks accepts the VP position, as he knows the party has to be united to crush the Democrats again. The Democrats nominate Senator Ben Tillman of South Carolina with Professor Woodrow Wilson to match the natolnalisn of Teddy. They fail and get an epic smackdown outside the Deep South, even losing Tennessee, Texas, and Virginia to the Republicans.
 
He would need to run for Governor again in order to be relevant by 1912.

Would this be a particularly difficult task though? Correct me if I'm wrong, but I think he enjoyed strong support from his state's Republican party and earned a very solid reputation for his performance a the job, and given he period the Republicans aren't exactly weak in he state. With both a strong local and national reputation, I would wager he can defeat a William Hearst type figure.
 
He’d be Trump a century sooner. And I don’t mean to drag this into current politics, but he would be best served by being a thorn in an elected Democrat’s side, rally the people as a populist, and getting nominated despite the GOP’s wishes. I only invoke Trump because I am aware of no better analogue historically for TR’s best route to the White House without some asshole capping McKinley.
 
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