Seven Times Teddy Roosevelt Should Have Died — But Somehow Didn’t

Published January 6, 2023
Updated April 3, 2024

Teddy Roosevelt In The Spanish-American War

Theodore Roosevelt And Rough Riders

Smith Collection/Gado/Getty ImagesColonel Theodore Roosevelt and Officers of the Rough Riders. 1898.

In 1886, Teddy Roosevelt decided to return to the “thick of the battle of New York.” He planned on making it as a politician. Instead, he’d see actual battle in Cuba during the Spanish-American War.

After spending more than a decade rising through the political ranks, Roosevelt decided to leave his post as Assistant Secretary of the Navy when the Spanish-American War broke out in 1898. He went to Cuba to lead a volunteer cavalry regiment called the Rough Riders.

There, the future president faced death on multiple occasions. During the Battle of Las Guasimas on June 24, bullets whizzed past Roosevelt’s head, hitting trees so close to him that splinters flew in his face, according to the National Park Service. Seven Rough Riders died; 34 were wounded.

Theodore Roosevelt On Horseback

Bettmann/Getty ImagesTeddy Roosevelt on horseback with the Rough Riders. Undated.

A week later, Roosevelt looked death in the eye once again. On July 1, which Roosevelt would later call “the greatest day” of his life, the future president led the Rough Riders up San Juan Hill. Riding his horse, Little Texas, and wielding a revolver recovered from the USS Maine, Roosevelt rode up and down the hill, barking out orders. The Americans won the battle, and Roosevelt emerged from the fray as a national hero.

“Lieutenant Colonel Roosevelt, in total disregard for his personal safety, and accompanied by only four or five men, led a desperate and gallant charge up San Juan Hill, encouraging his troops to continue the assault through withering enemy fire over open countryside,” Roosevelt’s Medal of Honor commendation, rewarded posthumously in 2001, read.

“Facing the enemy’s heavy fire, he displayed extraordinary bravery throughout the charge, and was the first to reach the enemy trenches, where he quickly killed one of the enemy with his pistol, allowing his men to continue the assault.”

Roosevelt’s newfound popularity propelled him into the governor’s mansion in New York and brought him into the upper echelons of politics as William McKinley’s vice president. And when McKinley was felled by an assassin’s bullet in 1901, 42-year-old Roosevelt took power.

Kaleena Fraga
A staff writer for All That's Interesting, Kaleena Fraga has also had her work featured in The Washington Post and Gastro Obscura, and she published a book on the Seattle food scene for the Eat Like A Local series. She graduated from Oberlin College, where she earned a dual degree in American History and French.
John Kuroski
John Kuroski is the editorial director of All That's Interesting. He graduated from New York University with a degree in history, earning a place in the Phi Alpha Theta honor society for history students. An editor at All That's Interesting since 2015, his areas of interest include modern history and true crime.
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Fraga, Kaleena. "Seven Times Teddy Roosevelt Should Have Died — But Somehow Didn’t.", January 6, 2023, Accessed June 22, 2024.