Among Theodore Roosevelt's many lifetime accomplishments, few capture the imagination as easily as his military service as a "Rough Rider" during the Spanish-American War. America had become interested in Cuba's liberation in the 1890s as publications portrayed the evil of Spanish Rule. No one favored Cuban independence more than Roosevelt. As Assistant Secretary of the Navy, he beat the war drum and prepared the Navy for war with Spain. The battleship USS Maine was dispatched to Havana, Cuba. After a few quiet months, anchored in Havana Harbor, the Maine suddenly exploded, killing 262 American sailors. Spain denied blowing up the Maine, but a US Navy investigation concluded that the explosion was caused by a mine. The cause of the explosion remains a mystery, but American journalists and Assistant Secretary Roosevelt, at the time, felt certain that it was a Spanish act of war. Shortly thereafter, war was declared.
Roosevelt served gallantly during this brief conflict, which lasted from May to July, 1898. An eager Roosevelt resigned his post of Assistant Secretary of the Navy and petitioned Secretary of War Alger to allow him to form a volunteer regiment. Although he had three years of experience as a captain with the National Guard, Roosevelt deferred leadership of the regiment to Leonard Wood, a war hero with whom he was friendly. Wood, as Colonel, and Roosevelt, as Lt. Colonel, began recruiting and organizing the First U.S. Volunteer Cavalry. They sorted through twenty-three thousand applications to form the regiment! Roosevelt's fame and personality turned him into the de-facto leader of this rag-tag group of polo players, hunters,cowboys, Native Americans, and athletic college buddies. The regiment of "Roosevelt's Rough Riders" was born.
The Rough Riders participated in two important battles in Cuba. The first action they saw occurred at the Battle of Las Guasimas on June 24, where the Spanish were driven away. The Rough Riders lost seven men with thirty-four wounded. Roosevelt narrowly avoided bullets buzzing by him into the trees, showering splinters around his face. He led troops in a flanking position and the Spanish fled. American forces then assembled for an assault on the city of Santiago through the San Juan Hills. Colonel Wood was promoted in the field, and in response, Roosevelt happily wrote,"I got my regiment."
The Battle of San Juan Heights was fought on July 1, which Roosevelt called "the great day of my life." He led a series of charges up Kettle Hill towards San Juan Heights on his horse, Texas, while the Rough Riders followed on foot. He rode up and down the hill encouraging his men with the orders to "March!" He killed one Spaniard with a revolver salvaged from the Maine. Other regiments continued alongside him, and the American flag was raised over San Juan Heights.
Hostilities ceased shortly after Santiago fell to siege, and the Treaty of Paris gave the United States its first possessions: Guam, Puerto Rico, and the Philippines.
The war had lasting impacts. The "splendid little war" lasted ten weeks. It destroyed the Spanish Empire and ushered in a new era of American Empire. Roosevelt's political career ignited as he returned a war hero and national celebrity. He charged on horseback to victory at Kettle Hill and, collectively, San Juan Heights, and continued riding that horse all the way to the White House just three years later. Roosevelt was posthumously awarded the Medal of Honor, one hundred years later, for what was described as "…acts of bravery on 1 July, 1898, near Santiago de Cuba, Republic of Cuba, while leading a daring charge up San Juan Hill."