23 Photos of Theodore Roosevelt's Legendary Life

Journey through Theodore Roosevelt’s incredible life with an image collection inspired by the History Vs. podcast.

From his epic African safari to his harrowing expedition in the Amazon—and not to mention the U.S. presidency—Theodore Roosevelt was never one to back down from a challenge. Journey through his daring, legendary life with this selection of images that depicts some of the exciting events covered in Mental Floss's History Vs. podcast. Subscribe here!

1. Theodore Roosevelt's Birthplace

This New York City brownstone at 28 East 20th Street is where Theodore Roosevelt was born on October 27, 1858. At the time, it was a much more residential neighborhood than today, with ample garden space and a large mansion property that housed cows, peacocks, and even exotic birds. It’s now the Theodore Roosevelt Birthplace National Historic Site.

2. The Sitting Room at TR's Childhood Home

This is the sitting room in the Theodore Roosevelt Birthplace National Historic Site. The building was partially torn down in the early 1900s, so we don’t know if this is exactly how the room looked when the Roosevelts lived there. The Women’s Roosevelt Memorial Association purchased the property after Roosevelt’s death in 1919 and reconstructed it as his sisters, Bamie and Corinne, remembered it.

3. Theodore and Elliott Roosevelt Watch Lincoln's Funeral Procession

On April 25, 1865, Abraham Lincoln’s funeral procession rambled through the streets of New York City. You can just make out the tiny heads of 6-year-old Theodore and his brother, Elliott, watching from the second-story window of their grandfather’s mansion.

4. Theodore Roosevelt as a Harvard Freshman

This portrait shows Theodore during his freshman year at Harvard University in 1876. Though he spent his childhood holed up in his room examining various dead animals, at college he joined clubs, made friends, and started filling every spare moment with activities like wrestling, rowing, and boxing.

5. Theodore Roosevelt as a Young New York State Assemblyman

Theodore Roosevelt was just 23 years old when he was elected to the New York State Assembly in 1881. This photo shows him as a New York State Assemblyman in 1884.

6. Theodore Roosevelt's Diary

On Valentine’s Day in 1884, Theodore Roosevelt's mother Mittie and his first wife Alice Hathaway Lee died. Later that day, TR drew a large X in his diary and wrote, “The light has gone out of my life.”

7. Theodore Roosevelt's Maltese Cross Cabin

Roosevelt purchased this cabin on North Dakota’s Maltese Cross cattle ranch in 1883 during a bison-hunting trip. He intended to relocate to the Dakotas permanently after the deaths of his wife and mother and a difficult final term as a New York State Assemblyman, but he soon discovered its riverside location made it much too public. In 1884, he bought the rights to a second, more secluded plot of land just 35 miles south, on which he built his Elkhorn Ranch cabin (which is no longer standing). He sold off the rights to both of his ranches in the 1890s. The Maltese Cross Cabin can be seen today at Theodore Roosevelt National Park in Medora, North Dakota.

8. Theodore Roosevelt Poses in His Hunting Suit

Theodore Roosevelt wearing his deerskin hunting suit in 1885. He had it made for his time in the Dakotas despite the fact that no one wore these types of suits there.

9. Theodore Roosevelt Poses with Bandits

In the spring of 1886, Theodore Roosevelt, along with ranch hands Bill Sewall and Wilmot Dow, pursued three thieves who had stolen his boat from Elkhorn Ranch. After the thieves had been apprehended, TR staged a photo of himself watching over the bandits.

10. TR as Police Commissioner of NYC

Theodore Roosevelt during his time as New York City Police Commissioner. Roosevelt was president of the board, which consisted of three other members, and served from 1895 to 1897.

11. TR with the Rough Riders

Theodore Roosevelt stands with the Rough Riders, a.k.a. the 1st Cavalry Volunteers, on San Juan Hill during the Spanish-American War.

12. Alice Roosevelt in 1902

Alice, Roosevelt’s only child from his first marriage, was photographed with her dog Leo in 1902. Spirited, dauntless Alice was the original White House wild child—and a major source of stress for her father. Once, during a 1905 diplomatic trip to the Far East, Alice issued a dare to her companions to jump into a steamship’s swimming tank ... then did it herself, fully clothed in a white silk outfit.

13. Roosevelt Family Portrait

Theodore Roosevelt and his family pose for a photo on July 12, 1903. Archie sits on his father’s knee, Quentin on his mother Edith’s, and the four other Roosevelt children are (L-R) Ethel, Ted, Alice, and Kermit.

14. TR Speaking to Suffragettes

Theodore Roosevelt addresses a crowd of 500 suffragettes from the porch of his Sagamore Hill home around 1905.

15. Alice's Wedding Day

Theodore Roosevelt (right) with his daughter Alice and her husband, Nicholas Longworth, on their wedding day in 1906.

16. Theodore Roosevelt with Russian and Japanese Dignitaries

Roosevelt stands between Russian and Japanese dignitaries in Portsmouth, New Hampshire, in 1905. On September 5, they signed the Treaty of Portsmouth, ending the Russo-Japanese War and earning Roosevelt the 1906 Nobel Peace Prize; he was the first American to win a Nobel Prize of any kind.

17. Theodore Roosevelt in Panama

In November 1906, Roosevelt operated a 95-ton railroad shovel in Panama, where the U.S. was in the process of building what would become the Panama Canal. The trip made him the first sitting president to set foot on foreign soil.

18. Theodore Roosevelt Poses with an Elephant He Killed in Africa

In 1909, weeks after his presidential term ended, Roosevelt and his son Kermit embarked on an African safari, during which they killed 512 animals. When faced with criticism for the excessive slaughter, Roosevelt insisted it was done in the name of science—and he did donate most of the specimens to the National Museum of Natural History and the American Museum of Natural History.

19. An X-Ray of the Bullet in Theodore Roosevelt's Chest

Roosevelt was shot just before a campaign speech in Milwaukee, Wisconsin, on October 14, 1912. He insisted on delivering the 90-minute address before allowing himself to be taken to the hospital. This X-ray photo of his chest shows where the bullet ended up.

20. Theodore Roosevelt's Bullet-Ridden Manuscript

The bullet had ripped right through the papers in Roosevelt’s pocket, and his spare eyeglasses case, before lodging itself in his chest.

21. Theodore Roosevelt on the Roosevelt-Rondon Scientific Expedition

Roosevelt is shown during his expedition to South America, where he explored the River of Doubt, a previously uncharted tributary of the Amazon River. At age 55, knowing that his adventuring days were limited, he called the trip “his last chance to be a boy.”

22. Theodore Roosevelt at His Libel Trial

Theodore Roosevelt posing with members of the press in Syracuse during his 1915 trial for libel.

23. Theodore Roosevelt's Gravesite

Theodore Roosevelt was buried at Youngs Memorial Cemetery in Oyster Bay, New York, a little over a mile from his home, Sagamore Hill. He died in his sleep on January 6, 1919, at age 60, after suffering a pulmonary embolism.