Theodore Roosevelt vetoed 82 bills (42 regular vetoes and 40 pocket vetoes), with one veto being overridden by Congress.

Prior to Roosevelt, only one president had issued over 200 executive orders, Grover Cleveland (253). The first 25 presidents issued a total of 1,262 executive orders combined. Roosevelt issued 1,081.

After serving two terms as a Republican president, Roosevelt had groomed William Howard Taft to succeed him in the 1908 presidential election. But soon after, Roosevelt said, "I am really sorry for Taft ... I am sure he means well, but he means well feebly, and he does not know how! He is utterly unfit for leadership and this is a time when we need leadership." In the election of 1912, Roosevelt ran as the Progressive Party ("Bull Moose") nominee, finishing second with 27.4% of the vote to Democrat Woodrow Wilson's 41.8%. This was the last presidential election in which one of the top-two finishers did not come from either the Democratic or Republican parties, signifying the primacy of these two parties in modern American politics.

On October 14, 1912, while campaigning in Milwaukee, Wisconsin, Roosevelt was shot by a saloonkeeper named John Flammang Schrank. The bullet lodged in his chest after penetrating his steel eyeglass case and passing through a 50-page single-folded copy of the speech that he was carrying in his jacket. He declined medical attention and delivered his scheduled speech with blood seeping from the wound. His opening comments to the gathered crowd were, "Ladies and gentlemen, I don't know whether you fully understand that I have just been shot, but it takes more than that to kill a Bull Moose." Afterwards, an x-ray showed that the bullet had lodged in Roosevelt's chest muscle, but did not penetrate the pleura. Doctors concluded that it might be dangerous to remove it, and Roosevelt carried the bullet with him for the rest of his life.

From left to right, Mount Rushmore features: 1) George Washington, 2) Thomas Jefferson, 3) Theodore Roosevelt, and 4) Abraham Lincoln. The four presidents were chosen to represent the nation's birth, growth, development, and preservation, respectively.

When he lost his fortune in the Dakota Territory in 1886 and needed to make a living to support his family, he did so by writing and continued to publish for the remainder of his life. Roosevelt wrote on a wide range of topics and genres, including history (The Naval War of 1812), autobiography, biography (Oliver Cromwell), commentary and editorials (whole series for the Kansas City Star and The Outlook), memoirs (of his experiences in Cuba leading the Rough Riders), nature (Summer Birds of the Adirondacks), and guide books (New York: Historic Towns). Altogether, he published about 47 books.