Teddy Roosevelt: Progressive.
Ronald Pestritto had an interesting column in yesterday's Wall Street Journal (available here) on Theodore Roosevelt. Here is a bit:
The fact that conservative politicians such as John McCain and writers like William Kristol and Karl Rove are attracted to our 26th president is strange because, if we want to understand where in the American political tradition the idea of unlimited, redistributive government came from, we need look no further than to Roosevelt and others who shared his outlook.

Progressives of both parties, including Roosevelt, were the original big-government liberals. They understood full well that the greatest obstacle to their schemes of social justice and equality of material condition was the U.S. Constitution as it was originally written and understood: as creating a national government of limited, enumerated powers that was dedicated to securing the individual natural rights of its citizens, especially liberty of contract and private property.

It was the Republican TR, who insisted in his 1910 speech on the "New Nationalism" that there was a "general right of the community to regulate" the earning of income and use of private property "to whatever degree the public welfare may require it." He was at one here with Democrat Woodrow Wilson, who had in 1885 condemned Americans' respect for their Constitution as "blind worship," and suggested that his countrymen dedicate themselves to the Declaration of Independence by leaving out its "preface" — i.e., the part of it that establishes the protection of equal natural rights as the permanent task of government. . . .

In his New Nationalism speech he noted how, in aiming to use state power to bring about economic equality, the government should permit a man to earn and keep his property "only so long as the gaining represents benefit to the community." The government itself of course would determine what represented a benefit to the community, and whether society would be better off if an individual's wealth was transferred to somebody else.

We can see the triumph of this outlook in progressive income taxation, which TR trumpeted in his speech (along with progressive estate taxes). We may also see this theory in action when a government seizes private property through eminent domain, transferring it to others in order to generate higher tax revenues — a practice blessed by the Supreme Court in its notorious Kelo v. New London decision of 2005. . . .
The column breaks no new ground. It is just a nice reminder of why TR is one of my least favorite of all the "respected" Presidents and should provide no role model for today's political class.

Update: Max Boot defends TR as a conservative here, mainly due to his foreign policy record that "should provide inspiration for today’s generation of conservatives" but also this bit:

Given that all but the most extreme libertarians have come to terms with the New Deal and considerable post-New Deal expansion of government (e.g., Medicare and Medicaid), it hardly makes sense to denounce TR as some kind of lefty for anticipating the kind of reforms that would make our capitalist system more stable and durable.
Boot provides a lengthy defense of TR as a conservative in World Affairs, in which he concludes:
TR’s philosophy is not for everyone. He represented one strain of conservatism among many—a reformist strain of which Benjamin Disraeli was the other leading exponent. But it was conservatism nonetheless. Attempts to read him out of the conservative canon have no more persuasive power than attempts to exclude John McCain. Indeed, the energetic brand of conservatism that both men embody fits the temper of our times better than the anti-government rhetoric that defined the conservative movement of a decade ago. Some of the most influential tomes on Republican reform, by the likes of Newt Gingrich, David Frum, and Ross Douthat and Reihan Salam, argue that the Grand Old Party needs to fashion itself more in TR’s image and less in Barry Goldwater’s and Robert Taft’s. The creed of these modern-day conservatives intentionally echoes Roosevelt’s: “It is not my intention to do away with government,” he said in his first inaugural address. “It is, rather, to make it work.”