You know Theodore Roosevelt as a larger-than-life President, but did you know his greatest military honor was awarded posthumously, over a century after his heroic actions? Roosevelt’s charge up San Juan Hill is legendary, but the story behind his Medal of Honor is a fascinating tale of battlefield bravery, political friction, and a long-overdue recognition for a man who defined American courage at the turn of the 20th century.
🎖️ The Charge of the Rough Riders
During the Spanish-American War in 1898, Roosevelt, then a Lieutenant Colonel, famously led his volunteer cavalry regiment, the ‘Rough Riders,’ in a daring charge. While often called the charge up San Juan Hill, his unit’s primary assault was on the adjacent Kettle Hill. Under heavy Spanish fire, Roosevelt, on horseback, rallied his men and others, leading them in a successful but costly assault that was pivotal in the American victory at the Battle of Santiago. His leadership and raw courage that day were undeniable, and he was immediately recommended for the Medal of Honor.
📜 A Century-Long Wait for Recognition
So why the long wait? Despite the clear evidence of his heroism, Roosevelt’s initial nomination was stalled, partly due to his own harsh criticism of the War Department’s leadership and logistical failures. The political establishment was not keen on awarding the nation’s highest honor to such a vocal critic. For decades, his case was overlooked. It wasn’t until a concerted effort by his descendants and congressional supporters that his case was reopened. In 2001, President Bill Clinton posthumously awarded the Medal of Honor to Theodore Roosevelt, finally cementing his legacy not just as a president, but as a recognized national war hero.
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“Theodore Roosevelt: Medal of Honor.” *Congressional Medal of Honor Society*, www.cmohs.org/recipients/theodore-roosevelt. Accessed 30 July 2025.
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