Theodore Roosevelt left the presidency at age fifty on March 4, 1909. Whatever regret or ambivalence he may have felt about his 1904 pledge not to run for re-election in 1908, he was at least pleased with his hand-picked successor, William Howard Taft. Taft had been secretary of war for the last five years of Roosevelt’s time in office. He seemed to share most of TR’s progressive economic values. But even before Election Day, Taft seemed to drift toward the more conservative, big business elements of the Republican Party. Theodore was worried.