This Day in History: Battle of San Juan Heights

On this day in 1898, Theodore Roosevelt and his Rough Riders famously charge up San Juan Hill. Roosevelt’s bravery captures the public imagination, launching him into national prominence.

“The charge itself was great fun,” he declared afterwards. “Oh, but we had a bully fight.”

But how much of his legendary reputation was earned on the battlefield—and how much was created by an adoring media eager to make him one of the Spanish-American War’s most famous heroes?

That conflict—later dubbed “a splendid little war”—was fought just as Cubans, Puerto Ricans, and Filipinos sought to free themselves from Spanish rule. Their plight earned the sympathy of many Americans, so when USS Maine exploded in Havana Harbor on February 15, 1898, some believed Spain had sabotaged the ship.

War was declared in April. Roosevelt was thrilled!

He resigned his Navy position and got permission to raise a volunteer regiment. That cavalry regiment was a “rag-tag group,” the National Park Service explains, “of polo players, hunters, cowboys, Native Americans, and athletic college buddies.”

Roosevelt valued his Rough Riders for their “thirst for adventure,” noting that they “were to a man born adventurers, in the old sense of the word.”

U.S. troops arrived in Cuba late in June 1898. By July 1, they were just outside Santiago, preparing to take nearby Kettle and San Juan Hills.

Believe it or not, Roosevelt wasn’t originally assigned to San Juan Hill. Instead, he and his men were to take Kettle Hill while others took San Juan. But Kettle Hill was taken first, so the Rough Riders joined the ongoing fight at San Juan Hill.

Roosevelt had started the day on a horse named Texas, but that horse got tangled up in barbed wire, leaving Roosevelt to finish the day on foot. None of that stopped a reporter from emphasizing the sight of Roosevelt riding hard.

“[H]e was, without doubt,” Richard Harding Davis wrote, “the most conspicuous figure in the charge. . . . Roosevelt, mounted high on horseback, and charging the rifle-pits at a gallop and quite alone, made you feel that you would like to cheer.”

Roosevelt would eventually receive a Medal of Honor, and that citation is just as enthusiastic. “[Col. Roosevelt] led a desperate and gallant charge up San Juan Hill,” it describes, “encouraging his troops to continue the assault through withering enemy fire . . . . [He] 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.”

But was Roosevelt really the driving force behind the American victory that day?

Historians such as Jerry Tuccille, author of The Roughest Riders: The Untold Story of the Black Soldiers in the Spanish-American War, assert that Roosevelt’s actions got too much attention because his allegedly “hand-picked reporters” embellished his role and downplayed others’ contributions. “The media loved him because he was a colorful character and an adventurer,” Tuccille concludes. “He was great copy.”

Defense Department historian Frank Schubert agrees: “Regulars and volunteers, blacks and whites, fought side by side . . . .They forged a victory that did not belong primarily to TR, nor did it belong mainly to the Buffalo soldiers. It belonged to all of them.”

Either way, the publicity transformed Roosevelt into a national hero. He became the public face of the victory at San Juan, and he used that fame to further his political career. He did not receive the Medal of Honor during his lifetime (to his great disappointment), but Congress finally awarded it posthumously in 2001.

Roosevelt called the Battle of San Juan Heights “the great day of my life.” Perhaps he was right.

Constitution4Kids.com

Primary Sources:

• The Encyclopedia of the Spanish-American and Philippine-American Wars: A Political, Social, and Military History (Spencer C. Tucker ed. 2009)

• H. W. Brands, T.R.: The Last Romantic (1997)

• Iván Román, The Buffalo Soldiers at San Juan Hill: What Really Happened? (History Channel)

• The Rough Riders Storm San Juan Hill, 1898 (Eyewitness to History)

• Theodore Roosevelt, The Rough Riders (1899) (available HERE)

• T. R. the Rough Rider: Hero of the Spanish American War (National Park Service: Theodore Roosevelt Birthplace)