Theodore Roosevelt: His Last Reunion of the Famed Rough Riders

The only autograph from TR’s final Rough Riders reunion we have seen reach the market

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 combat, and moving to have Congress allow for enlisting unlimited numbers of 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.  The new unit gathered in San Antonio for training, with TR actively involved.

After the war, the Rough Riders Association held reunions. In 1905, the Rough Riders held what would be the final such meeting in TR’s lifetime, and it coincided with the end of campaign season and the start of his second term  It was held in San Antonio, making for an emotional homecomin.  Approximately 50 veterans of the regiment showed up for a chance to re-live the glory days.

Between public appearances – including a review of the troops at Fort Sam Houston, a speech in Alamo Plaza and a visit to the old training grounds at Riverside Park – Roosevelt’s two-day trip included plenty of private time with his comrades. This included a lunch and private meeting the afternoon of the second day, and what must have been an emotional farewell later that night at the Menger Hotel.

Roosevelt’s popularity was fully reflected in the enthusiasm of newspaper coverage of his visit.  “With a warmth and feeling that cannot be described and which the most vivid imagination cannot exaggerate, San Antonio opened her arms to him and received him into the most sacred depths of the civic heart,” read one Daily Express article.

William Stiles was a resident of Williamson TX near San Antonio and made the trip to see Roosevelt at the hotel. He brought along his son, Walter, and introduced the boy to the President, who penned a moving and sympathetic note not only to father but to son. Walter was born in January of 1888.  Roosevelt himself had four sons, and his relationship with them is famous.  Moreover, the apple of his eye, Quentin, had been born two months before Walter, so he could understand having a 7-year-old son, full of life and energy and mischief.

“From the father of four boys of various ages, who bare all kinds of adventures and accidents, and are sometimes good and sometimes – well, not so good. Theodore Roosevelt.”

Document signed, for Roosevelt's farewell dinner, at the Menger Hotel, April 7, 1905, to Walter and William Stiles.  “From the father of four boys of various ages, who bare all kinds of adventures and accidents, and are sometimes good and sometimes – well, not so good. Theodore Roosevelt.”

The outside of the program has a gorgeous engraving of Roosevelt as Rough Rider and images of the American and Texas flags.  The inside contains the program, a musical set in two acts, as well as the menu of crepes, soft shell crabs, lamb, and wine, among other things.

This quotation is unpublished, and has been previously unknown. Nor have we ever seen anything from TR’s final Rough Riders reunion reach the market.