The Rough Riders

On April 25, 1898, Theodore Roosevelt resigned as Acting Secretary of the U.S. Navy and, together with Army Colonel Leonard Wood, formed the 1st U.S. Volunteer Cavalry Regiment. The newspapers had a name for them almost immediately: The Rough Riders.

Like many other volunteer units, the regiment was a temporary organization formed for the duration of the Spanish-American War. The men trained for several weeks in San Antonio, Texas. Roosevelt arrived on May 16, after securing modern Krag smokeless carbines capable of firing multiple rounds — a decisive advantage in the field.

The regiment used a mix of standard-issue gear and equipment of their own design, purchased with gift money. What truly set the Rough Riders apart, however, was the remarkable diversity within their ranks.

The Rough Riders were part of the cavalry division commanded by former Confederate General Joseph Wheeler, one of three divisions in V Corps under Lieutenant General William Rufus Shafter. Wood, Roosevelt, and their men departed Tampa on June 13, landed at Daiquiri, Cuba, on June 23, and marched to Siboney.

Wheeler dispatched elements of the 1st and 10th Regular Cavalry along the lower road northwest, while sending the 1st USV Rough Riders along a parallel ridge road running up from the beach. To outmaneuver an infantry rival, Wheeler held back the 9th Cavalry at Siboney — preserving the option to call his northward push a limited reconnaissance if things went wrong.

Roosevelt was promoted to Colonel and assumed command of the regiment when Wood moved up to lead the brigade. The Rough Riders then engaged in a brief skirmish at the Battle of Las Guasimas before pushing through Spanish resistance and, together with the Regulars, forcing the Spanish to abandon their entrenched positions.

Under Colonel Roosevelt's leadership, the Rough Riders became famous for their dual charges up Kettle Hill and San Juan Hill on July 1, 1898. Roosevelt had the only horse, riding back and forth between rifle pits at the forefront of the advance up Kettle Hill — an advance he urged forward with no orders from superiors. A barbed wire entanglement near the summit forced him to dismount and complete the climb on foot.

The victories came at a steep price: 200 soldiers were killed and 1,000 wounded. In August, Colonel Roosevelt and fellow officers demanded that the troops be returned home. Roosevelt would forever recall the Battle of San Juan Hill as “the great day of my life” and “my crowded hour.”

After returning to civilian life, Roosevelt preferred to be addressed as “Colonel Roosevelt” or simply “The Colonel.” The nickname “Teddy” remained far more popular with the public — though Roosevelt openly despised it. Those who worked closely with him called him “Colonel” or “Theodore.”

The 1st U.S. Volunteer Cavalry Regiment was a temporary organization born of a single war, but the spirit it embodied — courage, diversity, selfless service, and bold leadership — proved enduring. That spirit lives on today in the 1st U.S. Volunteer Cavalry Regiment – Rough Riders, Inc., proudly carrying the name and the legacy forward in Tampa, Florida.