Theodore Roosevelt
War in Cuba

With the beginning of the Spanish–American War in 1898, Roosevelt resigned as Assistant Secretary of the Navy. Along with Army Colonel Leonard Wood, he formed the First U.S. Volunteer Cavalry Regiment. His wife and many friends begged Roosevelt to remain in Washington, but Roosevelt was determined to see battle. When the newspapers reported the formation of the new regiment, Roosevelt and Wood were flooded with applications. Referred to by the press as the "Rough Riders", it was one of many temporary units active only during the war.

The regiment trained for several weeks in San Antonio, Texas; in his autobiography, Roosevelt wrote that his experience with the New York National Guard enabled him to immediately begin teaching basic soldiering skills. Diversity characterized the regiment, which included Ivy Leaguers, athletes, frontiersmen, Native Americans, hunters, miners, former soldiers, tradesmen, and sheriffs. The Rough Riders were part of the cavalry division commanded by former Confederate general Joseph Wheeler. Roosevelt and his men landed in Daiquirí, Cuba, on June 23, 1898, and marched to Siboney. Wheeler sent the Rough Riders on a parallel road northwest running along a ridge up from the beach. Roosevelt took command of the regiment; he had his first experience in combat when the Rough Riders met Spanish troops in a skirmish known as the Battle of Las Guasimas. They fought their way through Spanish resistance and, together with the Regulars, forced the Spaniards to abandon their positions.

On July 1, in a combined assault with the Regulars, under Roosevelt's leadership, the Rough Riders became famous for charges up Kettle Hill and San Juan Hill. Roosevelt was the only soldier on horseback, as he rode back and forth between rifle pits at the forefront of the advance up Kettle Hill, an advance that he urged despite the absence of orders. He was forced to walk up the last part of Kettle Hill because his horse had been entangled in barbed wire. The assaults would become known as the Battle of San Juan Heights. The victories came at a cost of 200 killed and 1,000 wounded.

In August, Roosevelt and other officers demanded the soldiers be returned home. Roosevelt recalled San Juan Heights as "the great day of my life". After returning to civilian life, Roosevelt preferred to be known as "Colonel Roosevelt" or "The Colonel"; "Teddy" remained much more popular with the public, though Roosevelt openly despised that moniker.
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