1908 Election WI: Roosevelt vs Conservative Republican vs Cleveland

This was an idea that popped into my head.

What if Roosevelt attempted to run for a second full term in 1908 instead of telling Taft to run, and the Republican officials, wanting to oust Roosevelt from power, rally behind a Conservative candidate (any ideas?) forcing Roosevelt to make an independent run under his Progressive banner four years earlier than this time? Also, to make matters more interesting for 1908, Cleveland both doesn’t have a heart attack and decides to try again and give Conservative Democrats a victory, meaning William Jennings Bryan both isn’t the candidate and won’t give his support to Cleveland.

How do you see this turning out with two conservative candidates and the Progressive Roosevelt?
 
Joseph Cannon or Philander Knox is probably your best bet for Conservative-Establishment Republicans. As for the result... the Dems would be shooting themselves in the foot by putting up another Bourbon Democrat candidate in '08; probably still manage to take the South but will lose out in the cities to either Cannon's political machines or Knox's capitalist supported media campaign. The contest between Roosevelt and Cannon/Knox probably depends a lot on just how much money Roosevelt can get: lacking the party infrastructure to support the mass campaign, he'd need alternative patronage.
 
If TR wants a third (or "second elective") term in 1908, he will get the GOP nomination in a flash. First of all, there are all the southern delegates, who represented very few actual voters and were entirely dependent on the president for patronage. (Taft in 1912 showed how they could be useful--and they would be as pro-TR in 1908 as they were pro-Taft in 1912.) Second, TR as president was hardly as "radical" as he would be in 1912; the conservatives may have had their disagreements with him (as did "radicals" like La Follette) but could work with him. And most important, Republicans of every stripe knew how popular he was, which is why so many begged him to reconsider his pledge not to run in 1908. There were enough straight-ticket voters that having a winner on the top of the ticket was essential for many Republican--progressive and conservative alike--to win their own races.

As for the Democrats, there are a number of reasons they won't nominate Cleveland, the most obvious being that he died in June 1908! Even apart from this, Parker in 1904 had shown the folly of the idea that the Democrats could beat TR by nominating a conservative. And even if Cleveland were alive, healthy and willing to run--and he wasn't the latter two even in 1904!--Cleveland would be the worst possible choice, not only because he was hated by the Bryan wing of the party much more than Parker was [1], but because by nominating him the Democrats would be throwing away the no-third-term issue against TR. (Or they would have to make lame "it's different when the terms aren't consecutive" arguments as TR himself would do in 1912.) Why in the world incur all these problems for the sake of a man who was associated in public opinion with the depression of the 1890's?

[1] Parker for all his conservatism had voted for Bryan in both 1896 and 1900.
 
The Bourbon Democrats at this point were a fairly discredited lot. They ran against TR in 1904 and got trounced.

I greatly admire Grover Cleveland but even if we waive away his fatal heart attack he's still man very much out of place in 1908 not just within his own party but with the political landscape at large. He wouldn't stand much of a chance even against a divided GOP that wouldn't be all that divided given TR's personal popularity.
 
It would all be a bit reminiscent of 1892.

That year, Populist James B Weaver took enough Republican votes to give Cleveland a landslide win, with a smaller popular vote than he got in losing to the Republicans four years earlier. In this alt-1908, he might get an even smaller percentage than in '92, yet get an even bigger electoral college win, so that his poorest popular vote gives him his biggest victory.
 
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