Help me pick a TR Related Timeline to Write

I've been doing allot of reading on populist and progressive eras of American history. And like many books on this period they all bring up Theodore Roosevelt in one way or another. I have been itching to start writing again and I really want to start fresh with a turn of the century timeline. I have two potential timeline ideas I want to run by you.

Idea One: There is no Spanish-American War (most likely PoD avoid the explosion on the USS Maine). Some immediate impacts of this would be that TR is not thrust onto the national scene. At this time he was well known in Washington DC and within the Republican Party but not as much by the wider public. This means that there is less incentive to put him on the Republican ticket in 1900. Avoiding the Spanish-American War would also keep Speaker Thomas Reed from resigning. Does this keep him in politics (and good health) enough for him to get another crack at the Republican Party nomination in 1904? With the US avoiding this war than the country and many politicians remain more war hungry when a potential war breaks out in Europe. This also leads to the question of Spanish possessions in the Caribbean and Pacific. How long does Spain hold onto Cuba and the Philippines? Can they hold on to Puerto Rico?

Idea Two (Working title "Killing a Bull Moose"): TR is killed at his speech in Milwaukee, Wisconsin on October 14th, 1912. I know the idea of Teddy being killed is verboten, but that's the idea. Does this lead to Taft winning the 1912 election, or does a dead TR still get votes? If Taft does win how does his second term go and how does he respond to war in Europe?
 
TR winning in 1912 would be fun to see his effect on American entry into WW1 and how large America's navy would become.
 
Reforms the Rough Riders and fights with the Imperial Japanese?

From 'The Wind and the Lion'-goes in with the Marines?

Federally funds the Wright Brothers?
 
Or have him run in 1908, which he wins easily

And then 1912, which should also be easy

1916, is easy if WW1 is going on

If you win WW1, 1920 is easy too.

Just keep going baby!
 
Idea Two (Working title "Killing a Bull Moose"): TR is killed at his speech in Milwaukee, Wisconsin on October 14th, 1912. I know the idea of Teddy being killed is verboten, but that's the idea. Does this lead to Taft winning the 1912 election, or does a dead TR still get votes? If Taft does win how does his second term go and how does he respond to war in Europe?

Taft certainly does not win.

TR'a votes were essentially disgruntled Republicans who viewed Taft as unelectable, but preferred someone other than a Democrat if at all possible. So most of them would have switched to Hiram Johnson or whoever replaced TR on the Bull Moose ticket, while the rest would have held their noses and voted for Wilson, as they were to do in 1916.
 
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Both seem ok, #1 is more interesting I think. I've been reading Rise of Theodore Roosevelt lately (after the later two), and I've compiled some ideas for TR pod's. Driftless already mentioned my Dude Senator from Dakota idea, if you want some alternate ideas, it could be:

1.) Alice Lee and Martha Bulloch Roosevelt don't die in 1884. This would have a profound impact on Theodore, not least of which he never remarries to Edith. It could be an interesting character piece rather then a political one.

2.) Theodore wins the 1886 NYC mayoral race. He lost to Abram Hewitt because labor radical Henry George was rumored to be winning on the last few hours before the polls close. The race was an interesting three way:

Hewitt 41%: (90,552 votes)
George 31%: (68,110 votes)
Roosevelt 27%: (60,435 votes)

So if you can have a better Roosevelt campaign, or a worse George/Hewitt one, that means he becomes the 28 year old Mayor of America's biggest city. Definitely a game changer.

3.) Roosevelt never makes his pledge to serve only one term (well the one after McKinley's ran out), and maybe we'd see him try to hang on beyond the 1908 election.
 
Or have him run in 1908, which he wins easily

And then 1912, which should also be easy

1916, is easy if WW1 is going on

If you win WW1, 1920 is easy too.

Just keep going baby!

If he wins in 1908 he won't run in 1912.

His renunciation of a 1908 run shows that he basically believed in the two-term limit. Even if he might stretch it to apply only to elected terms and/or consecutive ones, he won't repudiate it outright - and his support would tumble quite a bit if he did.
 
Go East , Young Man !

Suppose when his wife and mother both die in February 1884, instead of heartbrokenly going west to the Dakotas, he goes east to England and gets involves in politics there?
 
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