Theodore Roosevelt Appoints a Commander of the Rough Riders

The Rough Riders are one of the most famous fighting units in American history, and his leadership of them made Theodore Roosevelt’s career. In April of 1897 TR was appointed Assistant Secretary of the Navy as a reward for his tireless campaigning for the newly elected President, William McKinley. When the U.S.S. Maine blew up in Havana harbor, the Spanish were blamed and an outcry for war arose. From that moment, Roosevelt believed that trying to prevent the war would be impossible. He sprang into action, moving ammunition, readying ships for action, and moving to have Congress allow for enlisting unlimited sailors. TR also made it known to the President and others that if war came, he wanted to leave his post behind a desk in Washington and head for the front.

Congress declared war on April 25, 1898, and that same day Roosevelt was officially offered (and accepted) second in command of the Rough Riders; he would soon take over full command of the unit. He immediately set about assembling and training the regiment, which was made up of an effective assemblage of Western cowboys and frontiersmen, and Eastern athletes and sons of prominent citizens. This composition reflected TR’s own interests. The unit was mustered into service between May 1 and May 21, 1898 in various locations in Texas, New Mexico and what was then termed “Indian Territory” (Arizona and Oklahoma). At the time of muster in, the unit consisted of 47 officers and 994 enlisted men. It was trained quickly in San Antonio, Texas, and on May 27 it was ordered to Port Tampa, Florida, to prepare for the invasion of Cuba. It left for the front in Cuba on June 13. One of these Rough Riders was Woodbury Kane, whom TR describes as “a close friend of mine at Harvard” in his autobiographical “The Rough Riders: An Autobiography.” Roosevelt organized his Rough Riders into 12 troops, from A through M.  Kane was the leader of K Troop.  

The Battle of San Juan Hill took place on July 1, 1898, and it proved to be a decisive battle in the Spanish-American War. The San Juan heights was a north-south running elevation about two kilometers east of Santiago de Cuba, the Americans’ main objective. This fight for the heights was the bloodiest battle of the war, and it was also the site of the greatest victory for the Rough Riders. General Lawton considered it strategically necessary to cover his flank by taking the nearby town of El Caney preparatory to assaulting Santiago. The Spanish had turned the town into a virtual fort, houses along each small street serving as well defended barricades to any opposing force. They were well entrenched inside six heavy timber blockhouses and held a fortified stone church at the highest point of the town, called El Viso. The Rough Riders and other U.S. troops attacked the town, and the battle there continued through the morning until successful. Then, astride his pony Texas, Colonel Roosevelt hurried his regiment across the knee-deep ford of the San Juan River and into position below San Juan Hill.  What followed was the charge up San Juan and Kettle Hills that made the regiment and its commander Theodore Roosevelt famous, and led to his becoming President of the United States just three years later.

Woodbury Kane entered Harvard University in the autumn of 1878, where he began his friendship with Theodore Roosevelt. When the Spanish–American War broke out in late April 1898, Kane enlisted in the First United States Volunteer Cavalry, or the Rough Riders. He was in fact one of Roosevelt’s first appointments. The New York Times, on May 7, 1898, wrote, “Mr. Roosevelt has had applications from almost every clubman… not only in New York, but in Boston and other large cities…. The most notable accessions to the ranks of this regiment from the New York clubs are Woodbury Kane, William Tiffany, Craig Wadsworth, and Reginald Ronalds, who started for Washington on Wednesday. These men, all members of the Knickerbocker Club, are intimate friends of Mr. Roosevelt, and all have volunteered as troopers. Woodbury Kane is a younger brother of Col. Kane, and is a noted polo player and cross-country rider. He has hunted not only in America, but with the more famous packs of England. He is a bachelor of about thirty-eight and a graduate or Harvard."

On July 1, 1898, in the assault on San Juan Hill by the Rough Riders, Kane famously led K Troop in the charge. He is the most visible person in Frederic Remington’s famous depiction of the event. Kane was wounded in the forearm and arm. For his wounds, he was awarded a citation for gallantry and was promoted to captain in the volunteer service. TR, in his book, described Kane as “…leading in the charges and always being nearest to the enemy…”

On August 2, Spain accepted the U.S. proposals for peace. The Rough Riders left Cuba soon after, and they arrived back in the U.S. at Montauk Point on Long Island on August 14.

This is Kane’s appointment on joining the Rough Riders.  Document signed, August 14, 1898, “on board transport Miami,” appointing Kane “Sergeant in Troop K of the 1st Regiment of US Cavalry Volunteers in the service of the United States, to rank as such from the eleventh of May, 1898.”  The document is dated the day the Rough Riders returned to the United States, because, as Kane has noted on the document, “the Regt from May till Aug was without these blanks being in the field.”

Kane was one of the most important men in Roosevelt’s Rough Riders and one of TR’s oldest friends, making this a remarkable appointment.