It's not that sad. Teddy Roosevelt was a progressive (though he was very imperialistic). Eisenhower was a moderate. There was actually a movement within the Democratic Party to boot Truman and nominate Ike in 1948, before he declared himself a supported of either party.
Teddy Roosevelt's progressiveness has been overstated. Aside from his massive imperialist actions (various Central and South American countries, the Philippines and advocating entry into WW1), he used soldiers as scabs and reduced the power of unions. Also a supporter of eugenics.
By today's standards, he wouldn't be considered progressive, but he died nearly 100 years ago. You have to consider the social, cultural, and political realities of the time when thinking about political history. He was very racist and imperialistic, but most Americans were at that moment in history. The Wilson administration is considered to be one of the high points of the American progressive movement, and Wilson was sympathetic with the KKK. Roosevelt had a mixed record on labor issues. He may have used scabs, but he did intervene in favor of strikers in at least one instance. And, maybe I'm wrong, but I don't recall him using military force to break strikes, unlike many of his predecessors and successors. That doesn't sound like much, but it's a huge step forward.
You also can't ignore his contributions to conservationism and food and drug safety laws. The National Park system and FDA are almost sacrosanct today, but getting them created was a huge (and very progressive) accomplishment. He was also the first president to try (and fail) to implement progressive health care reform. Incidentally, he was the first president to be accused of being a socialist while trying to implement healthcare reform.
That being said, I actually do think that TR is overrated. His imperialistic interpretation of the Monroe Doctrine was above and beyond what was reasonable, even for that era. Personally, I would have voted for Eugene V. Debs every time he ran (which includes all of the years that Roosevelt was a candidate for VP or President). However, you cannot throw out the progressive label just because he did a handful of things that were not progressive or even anti-progressive. FDR is arguably the most liberal/progressive president that we ever had, in spite of Japanese internment.
The Progressive Party nominated Teddy in 1912 for a reason.
Wait... weren't we talking about Romney's VP choice? Brian, or something like that?
