Theodore Roosevelt pretty much defined the Progressive Era of US History.
He was proud to call himself a “progressive”. It’s ridiculous to argue otherwise. The name of TR’s party in the 1912 election was the 1912 PROGRESSIVE PARTY.
According to Wikipedia, “Its platform called for women’s suffrage, recall of judicial decisions, easier amendment of the U.S. Constitution, social welfare legislation for women and children, workers’ compensation, limited injunctions in strikes, farm relief, revision of banking to assure an elastic currency, required health insurance in industry, new inheritance taxes and income taxes, improvement of inland waterways, and limitation of naval armaments.”
TR favored big government, Federal bureaucratic intrusion, imperial expansion, and big labor, while opposing private enterprise.
As a result, high school and college instructors probably loved him. Evidently he is still viewed favorably by modern conservatives of the “national greatness” variety.
http://en.wikipedia.org/wiki/Progressive_Era
http://en.wikipedia.org/wiki/Progressive_Party_%28United_States%2C_1912%29
Maybe that's another first for him. Lately, retired politicians take off to New York where they get refashioned by the intelligentsia into a much more liberal pattern.
That certainly happened with Teddy, though I can't think of any earlier politicians who went that route.