Colonel Theodore Roosevelt, Writing from Cuba, Reports on the Condition and Casualties of His Famed Rough Riders

A search of public sale records going back 40 years turns up just two letters of Roosevelt datelined from Cuba, this and another we handled back in 2009

The “Rough Riders” is a name given by the press to the First US Volunteer Cavalry, which was raised for the Spanish-American War. Secretary of War Russell Alger offered command of the regiment to Theodore Roosevelt, who resigned as Assistant Secretary of the Navy to take the field. The regiment was mustered-in in May 1898 and many of the volunteers had known Roosevelt from the Badlands of the Dakota Territory as well as his time as New York City Police Commissioner. There were more applicants than positions available and Roosevelt had to turn away large numbers of them. TR’s unit formed part of the 2nd Cavalry Brigade.

The regiment departed Tampa, Florida on June 14, 1898, landing near Daiquirí, Cuba on June 22. Although officially a cavalry unit, the regiment fought on foot. They immediately began marching toward their objective, Santiago. Two days later, the unit participated in the Battle of Las Guasimas. 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. All told, in Cuba, the Rough Riders suffered a casualty rate of about 76% lost in battle, wounded, or down with disease. A few days after the Rough Riders’ charge, the Spanish fleet fled Cuba. It was just a matter of weeks before the war had ended and the U.S. was victorious. The Rough Riders made headlines for their role in the battle back in the states, which became stuff of legend thanks to Roosevelt’s writing ability and reenactments filmed long after. The unit became famous, and its commander was on the road to the White House.

Typed letter signed, “First Regt. U.S. Vol. Cavalry / In camp near Santiago de Cuba”, July 27, 1898, to Emily [Mrs. Donald] McLean, President-General of the Daughters of the American Revolution in New York, who had supplied hammocks for the Rough Riders, giving her a report on the condition of the Rough Riders. “My dear Mrs. McLean, Those hammocks will be excellent for our men and I shall accept them with the utmost gratitude. Remember me warmly to your husband.

“We have had a pretty rough time of it here. Half of my men have been killed, wounded or prostrated by fever or dysentery and we have utterly lacked good food, shelter, clothing and medical supplies and assistance. If only now we are left to let go home to recuperate or sent on the expedition to Porto Rico, I shall be satisfied; but I wish they would not keep us here to catch the yellow fever, unless, of course, there is some real necessity for it. Faithfully yours, Theodore Roosevelt.”

On August 7, after 47 days in Cuba, the Rough Riders left Santiago harbor aboard the transport Miami headed for Montauk, Long Island. They arrived to a heroes’ welcome on August 14.

A search of public sale records going back 40 years turns up just two letters of Roosevelt datelined from Cuba, this and another we handled back in 2009.