The historical figure who famously led the charge at the Battle of San Juan Hill was Theodore Roosevelt. During the Spanish-American War in 1898, Roosevelt commanded the Rough Riders, a volunteer cavalry regiment. His leadership during this iconic battle showcased his bravery and decisiveness, ultimately contributing to an American victory in Cuba. Roosevelt's actions elevated his public image and laid the groundwork for his future political career, leading him to the presidency. His charge at San Juan Hill remains a symbol of American military valor.