Taft initially served under President Roosevelt as his secretary of war. A jolly, affable sidekick, Taft perfectly complemented the president's brash and intimidating demeanor. Their common political passions and close friendship eventually led to Roosevelt's glowing endorsement of Taft as his successor. When Taft's slow, deliberate style of leadership proved ill-suited to the intense pressures of the high office, Roosevelt attempted to unseat his political progeny by running against him for a non-consecutive third term.

Roosevelt took a radical approach in his campaign, challenging the authority of Taft's beloved Supreme Court. Taft reacted by branding him a "freak" and a "dangerous demagogue." Roosevelt lost the Republican nomination, but swiftly shifted his allegiance to the Progressive Party to stay in the race. In the end, both would be defeated by a less embattled candidate, Woodrow Wilson of the Democratic party. Taft went on to become chief justice of the United States, the job he had always coveted.