As the 1908 Presidential election approached, many Republicans and the American public as a whole clamored for their beloved Teddy to run for third term as President. Technically, Roosevelt had run only once before, in 1904–he had become President by law after William McKinley's death, and there was no legal restriction against his running for a third term. (At this time, the Twenty-second Amendment to the Constitution–which bars Presidents from serving more than two terms–had not yet been passed). Precedence, however, dictated against Roosevelt running again. No single president, even in the Colonial era, had ever served more than two terms in office, and Roosevelt believed that tradition should not be broken. Despite popular support, he made it clear that he would not run for a third term.

Yet Roosevelt also knew that if he did not run, the Republican Party might split between his loyal supporters and supporters of another candidate, and thus allow a non-Republican to win the election. To prevent this, he followed the advice of his political advisors and selected a successor, someone he could nominate at the upcoming Republican convention to please both his supporters and the traditional Republicans who valued Washington's precedence. He made sure that his long-time friend Senator Henry Cabot Lodge presided over the convention so that he could control the floor. The plan worked, and Roosevelt's faithful political ally William Howard Taft was nominated as the Republican presidential candidate. During Roosevelt's administrations, Taft had served as Governor of the Philippines and as Secretary of War. Taft won the rather uninteresting election of 1908 against the Democrats' third time nominee William Jennings Bryan, 321 electoral votes to 162.

With Taft secured in office as President, Roosevelt turned to more exciting matters, namely a safari through Africa to hunt big game. Not surprisingly, the African adventure thrilled Roosevelt. Along with his son Kermit, he departed New Jersey on March 1909 and spent eleven months on the hunt in Africa. During his trip he bagged 296 kills, including nine lions, eight elephants, thirteen rhinoceroses, fifteen zebras, and seven hippopotami. Kermit made 216 kills. The American public at home had a "bully" good time (one of Roosevelt's favorite expressions) keeping up with their ex-President. While in Africa, Roosevelt made regular submissions to Scribner's Magazine and later published the book African Game Trails about his adventures. After eleven months of hunting, the he and Kermit joined Edith and Ethel Roosevelt in Khartoum, Sudan, for sightseeing. Before returning home, Roosevelt also made a tour through Europe to deliver a series of lectures at prestigious universities. He also visited many of the continent's rulers, including the King of Italy, the German Kaiser Wilhelm II, and King Edward VII of England, who died during Roosevelt's visit. The Roosevelt family returned home in June 1910.

Although Theodore was grateful to return home after the exhausting trip, he was not pleased with President Taft, who had succeeded in alienating the Progressives from the Republican Party during Roosevelt's trip in Europe. Taft had been an excellent subordinate to Roosevelt, but was only an average President. He was a yes-man, greatly influenced by members of his family and the interests of big business. His administration looked especially weak compared to his predecessor's. When Roosevelt returned to the United States, he took it upon himself to reunite the Grand Old Party. He made speeches throughout America to appeal to Progressives and to conservative Republicans alike. Meanwhile, the friendship that had existed between Taft and Roosevelt slowly deteriorated until the two stopped talking to each other altogether. The final blow to the friendship came on October 27, 1911–Roosevelt's fifty-third birthday–when Taft filed a government antitrust lawsuit against U.S. Steel. Roosevelt had promised financier J.P. Morgan during the Panic of 1907 that the U.S. Steel Corporation would not be charged under the Sherman Act if Morgan could keep the country out of an economic depression. Taft's lawsuit encouraged scores of Roosevelt's supporters to call on him at Sagamore Hill and ask him to run once again for the presidency.

At first, Roosevelt declined their requests to run for a third term. He had stated previously that under no circumstances would he run again. Soon, however, these traditional sentiments began to wear off, and Roosevelt changed his tune. As more and more Progressives begged him to campaign again, Roosevelt acquiesced, and the fight between Roosevelt and Taft grew hot and intense. During the presidential campaign of 1912, both men railed against each other as only enemies could. Roosevelt called Taft disloyal and claimed him to be a fraud. Taft replied that Roosevelt was unethical and egotistical. The nation had never seen such a frenzy of insults and hatred as it did during this campaign, and Republicans were forced to choose sides in the battle. The extent of the rift in the Party was evident at the Republican convention in the Chicago. When President Taft received the party nomination, Roosevelt and his Progressive supporters left the convention hall and within hours formed the Progressive Party. Needless to say, the new Progressive Party nominated Roosevelt as their presidential candidate. When asked by a reporter if he was fit for the rigors of another Presidential campaign, Roosevelt replied that he was as fit as a bull moose. The phrase stuck, and Roosevelt's new party came to be known as the Bull Moose Party.

While the Republicans had been embroiled in their heated debate over Roosevelt and Taft, the Democrats had for the first time in years nominated someone other than William Jennings Bryan. Their new candidate was Woodrow Wilson, a former professor of jurisprudence and political economy at Princeton University and former president of the same institution. In 1910, he had been elected as Governor of New Jersey and had quickly won a reputation for his progressive policies. With his eloquent speeches and political dynamism, he was the obvious candidate for the 1912 Presidential election. Interestingly, a fourth candidate entered the race as well, a man named Eugene V. Debs, who ran on the Socialist Party ticket.

The four-candidate campaign was intense, especially for Roosevelt. On October 14, 1912, just one month shy of Election Day, Roosevelt was shot in the chest in an assassination attempt during a speech to a crowd in Milwaukee, Wisconsin. He narrowly escaped death, as the bullet hit a metal spectacle case in his breast pocket and was deflected away from his heart and lungs. The crowd seized the would-be assassin, a fanatic named John Crank, but Roosevelt instructed them not to harm him. Despite the bullet lodged in his chest, Teddy played to the crowd and continued to give the speech anyway. Afterwards, he claimed that the metal spectacle case had not been the only reason he lived; the surgeon who retrieved the bullet said that Roosevelt's extraordinary physical condition and muscular frame had stopped the bullet and prevented any serious damage. Theodore never found out why Crank had tried to assassinate him.

When the votes were tallied after Election Day, the results were not surprising: Democrat Woodrow Wilson had won, primarily because Taft and Roosevelt had shattered the Republican Party in their personal feud and political battle to receive the nomination. After the defeat, Roosevelt convinced the Progressives to rejoin the Republican Party.

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