Prior to leaving office in March of 1909, Roosevelt worked hard to get his friend and current Secretary of War William Howard Taft elected to carry on his policies. In order to give Taft a chance to set up his administration without the press constantly asking Roosevelt his opinions, T.R. took a long planned trip to Africa for a safari. His son Kermit accompanied T.R. on the trip. Roosevelt himself would promote the trip as one of scientific importance. He planned on sending the stuffed prey back to the Smithsonian museum for an exposition on mammal life in East Africa. He also planned to subsidize his trip by writing a series of articles for Scribner's magazine, at a tune of $50,000 for twelve articles. The articles would then be compiled in a book format for which Roosevelt would receive the royalties.

On the trip Roosevelt would kill hundreds of animals including eight elephants, thirteen rhinoceroses, nine lions, twenty zebra, seven hippopotamuses, seven giraffes, six buffalo, and many other mammals and birds. Roosevelt tells of the killing of one of the lions in this way as they rode up to a thicket.

We rode up to it and shouted loudly. The response was immediate, in the shape of loud gruntings, and crashings through the thick brush. We were off our horses in an instant, I throwing the reins over the head of mine; and without delay the good old fellow began placidly grazing, quite unmoved by the ominous sounds immediately in front. I sprang to one side; and for a second or two we waited, uncertain whether we should see the lions charging out ten yards distant, or running away. Fortunately, they adopted the latter course. Right in front of me, thirty yards off, there appeared, from behind the bushes which had first screened him from my eyes, the tawny, galloping form of a big, maneless lion. Crack! the Winchester spoke; and as the soft-nosed bullet ploughed forward through his flank the lion swerved so that I missed him with the second shot; but my third bullet went through the spine and forward into his chest. Down he came, sixty yards off, his hind quarters dragging, his head up, his ears back, his jaws open and lips drawn up in a prodigious snarl, as he endeavored to turn to face us. His back was broken; but of this we could not at the moment be sure, and if it had been merely grazed, he might have recovered, and then, even though dying, his charge might have done mischief. So Kermit, Sir Alfred, and I fired, almost together, into his chest. His head sank, and he died.

Such were the writings of Theodore Roosevelt in Scribner's magazine. With each article his popularity at home grew even more. The safari itself lasted nearly a full year, ending in March of 1910. The trip proved to be more expensive than T.R. had imagined, and thus during the trip he succussfully aqiuired a sum of $30,000 dollars from the U.S. philanthropist Andrew Carnegie. The trip culminated with a whirlwind tour of Europe in which every nation wanted to get a visit from the very popular former U.S. President. By Roosevelt's return to the United States, he was even more popular then when he made his historic return as a war hero after the Spanish American War.

As time wore on Roosevelt's thirst for power and the challenges of running the nation grew, and his opinions toward Taft's ability to lead the nation lessened. By 1912 Roosevelt was once again seeking the Republican nomination for the presidency. The Republican convention would take place in Chicago and the big money of the party was fully behind Taft. They big financiers had not forgotten Roosevelt's trust busting tendencies, and for them Taft was much more palatable. At the outset of the convention nearly 250 votes were in a state of flux. Should Roosevelt pick up 70 of those votes, the nomination would be his. Here the old guard Republicans stacked the cards against Roosevelt as a committee heavily stacked in Taft's favor would decide who the delegates would be. When Roosevelt failed to win the nomination his supporters bolted from the party, and began a new Progressive Party with Roosevelt as their candidate. The split of the Republican party would almost guarantee the election would fall to the Democrat Woodrow Wilson.

The Progressives moved very fast to raise money and to kick off the campaign. Roosevelt back on the stump was a might campaigner. On a train stop in Milwaukee on October 14, Roosevelt on his way to the auditorium, where he was to speak, was shot in the chest by an unknown gunman at close range. Fortunately for Roosevelt the bullet first went through the thick manuscript he was preparing to speak from before it struck his metal eyeglass case. The two obstructions reduced the velocity of the bullet enough that the shot wasn't fatal. Doctor's examined T.R. and ordered him to the hospital at once. T.R. refused to be denied his opportunity to speak to the crowd, and proceeded to give the speech with the bullet in his chest. He began the speech with the following words: "Friends, I shall ask you to be as quiet as possible. 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." The Progressive Party has often been referred to as the "Bull Moose Party". Despite this speech, when the election results were in Roosevelt finished second to Wilson and ahead of Taft. The final tally showed Wilson with 6.3 million votes to 4.1 million for Roosevelt and 3.5 million for Taft.

For a short period of time in the spring and summer of 1913 Roosevelt would return to his writing, working on his autobiography, and critiquing Wilson. Soon however his urge for adventure returned and he planned a trip to South America with Kermit to chart some of the uncharted waters of the Amazon River. Many problems arose on the trip. The river had many areas where the boats could not navigate the river, and had to be carried, thus causing the trip to be greatly extended. Food supplies and medicine ran very short. At one point when some of the boats got away, T.R. jumped into the water to rescue them and save the supplies and in the process reinjured the leg that had been damaged in the run away trolley car accident. Roosevelt developed a high fever, and with food being rationed there were moments when it was believed he would not survive the trip. Roosevelt, because of his own inability to help the boatman, volunteered to reduce his own rations even further so that the boatmen could have more. Five hundred miles of river and sixty days after the journey began they reached the end of their journey. Roosevelt once again subsidized his trip with articles to Scribner's magazine.

Upon his return to the states, Roosevelt once again took up the pen against Wilson. The war in Europe had begun and Wilson's nonintervention policy grated on Roosevelt's sense of honor and duty for the nation. He vehemently wrote about Wilson even to friends in Europe. When Wilson finally was forced to take the nation to war, T.R. petitioned the President to once again let him recruit a division of volunteers like the Rough Riders to take to war with himself as commander. Wilson would deny him that opportunity. Even so the old war hero would manage to play a part in the war by sending his four sons off to war. News reached home of Quentin being a war hero as he had managed to shoot down a German aircraft in a dogfight. Within a week, however, news reached the Roosevelt home that Quentin had been shot down. It wasn't until days later that news finally arrived that he had been killed. Both Ted and Archie would receive wounds during the war. Kermit being the only one escaping injury.

At the end of 1918 Roosevelt's health had declined, diagnosed as inflammatory rheumatism, not to mention the drain on his body from the infection in his leg after the Amazon trip. On January 5, 1919 before going to bed he told Edith that he felt strange as if his heart or breathing were about to stop. To help him gain a restful night of sleep a nurse injected a shot of morphine. At 4:15 in the morning his breathing stopped. Archie would pass the news on to his brothers across the ocean saying "The old lion is dead."