President Theodore Roosevelt Reminisces About His Rough Rider Days in Santiago, Cuba

The most famous of all the units fighting in the Spanish-American War, or perhaps any American war, was the “Rough Riders”, the name given to the First U.S. Volunteer Cavalry under the leadership of Theodore Roosevelt. Roosevelt resigned his position as Assistant Secretary of the Navy in May 1898 to join the volunteer cavalry. The original plan for this unit called for filling it with men from the Indian Territory, New Mexico, Arizona, and Oklahoma. However, once Roosevelt joined the group, it quickly became the place for a mix of troops ranging from wealthy Eastern adventurers to Western cowboys to Texas Rangers and Indians. The Rough Riders went to Tampa at the end of May and sailed for Cuba on June 13. There they joined the Fifth Corps, another highly trained, well supplied, and enthusiastic group consisting of excellent soldiers from the regular army and volunteers.

The Rough Riders saw battle at Las Guásimas, three miles north of Siboney on the way to Santiago. Though outnumbered, the American contingent was nonetheless able to force a retreat of the Spanish troops to the city of Santiago. On June 30, Roosevelt was promoted to full colonel and given formal command of the Rough Riders. The next day, American forces began an assault on the city of Santiago. The Rough Riders charged up Kettle Hill that was slightly to the north of San Juan Hill, though history recalls this as a charge up San Juan Hill. Roosevelt was the only one who was mounted; the others were on foot during battle. Spanish forces eventually surrendered on July 17. The Rough Riders made headlines for their role in the Battle of San Juan Hill. The Spanish-American War did not last long, but it was long enough for the Rough Riders to take San Juan Hill and pass into folklore. Roosevelt returned to the United States as the most famous man in the nation. Three years later he was President.

John F. Weston was a Union Army officer in the Civil War and a recipient of the United States military’s highest decoration, the Medal of Honor, for his actions during a raid on Confederate shipping. He was a brigadier general in the Spanish American war, serving as commissary general for General William Shafter, commander of the U.S. Army forces fighting at Santiago, Cuba. Thus did he meet Theodore Roosevelt.

Typed letter signed, as President, on White House letterhead, Washington, February 25, 1909, just a week before he left office, to General Weston, reminiscing about his Rough Rider days. “I have your letter of the 30th and it was good to hear from you. You are one of the men whose friendship I value, and I prize the memory of our service together.” He adds in holograph at the end, “at Santiago.”