Theodore Roosevelt Recalls Rough Rider Service with Old Colleague

"You are one of those men whose friendship I value, and I prize the memory of our service together at Santiago."

Just days before leaving office, President Theodore Roosevelt wrote this letter to an old friend from his military service in the Spanish-American War, Major General John F. Weston, who would retire from the U.S. Army later that year. Roosevelt recalled serving together with Weston in Santiago, Cuba, where Weston served as commissary general and Roosevelt led his famed Rough Riders.

THEODORE ROOSEVELT, Typed Letter Signed, to John F. Weston, February 25, 1909, Washington, D.C. On White House stationery. 1 p., 7" x 8.75". Expected folds; with signature and emendation by Roosevelt.

Complete Transcript
The White House / Washington
February 25, 1909.
My dear General:
I have your letter of the 20th and it was good to hear from you. You are one of those men whose friendship I value, and I prize the memory of our service together at Santiago.
With all good wishes, believe me,
Faithfully yours,
Theodore Roosevelt
Major General J. F. Weston, U.S.A.,
Department of California,
San Francisco, California.

Historical Background
In April 1898, Roosevelt resigned from his position as Assistant Secretary of the Navy. With Colonel Leonard Wood, Lt. Colonel Roosevelt formed the 1st U.S. Volunteer Cavalry regiment (dubbed the Rough Riders), composed of a diverse variety of men from across the nation and from many backgrounds and professions. Soon after landing in Cuba, Wood was put in command of the brigade and Roosevelt was promoted to command of the regiment.

On July 1, at the battle of San Juan Hill, the Rough Riders fought alongside the African American soldiers of the 24th Infantry and the 9th and 10th Cavalry. Effective use of Gatling machine guns reduced the strength of the defenders who had a superior position, the Americans took Kettle Hill and San Juan Hill. The Americans suffered approximately 2,000 casualties, including 200 killed. Despite the casualties, it was a decisive victory. American forces gained a strategic position from which to attack the main Spanish garrison in the city of Santiago de Cuba, which surrendered two weeks later.

Theodore Roosevelt (1858-1919) was born in New York City, graduated from Harvard University in 1880, and attended Columbia Law School. In 1880, he married Alice Hathaway Lee (1861-1884), with whom he had one daughter. Two days after their daughter's birth, Alice Roosevelt died, plunging Roosevelt into grief. He served in the New York State Assembly from 1882 to 1884, as president of the New York City Police Commissioners in 1895 and 1896, then as Assistant Secretary of the Navy from 1897 to 1898. After service in Cuba during the Spanish-American War, he won election as Governor of New York and served from 1899 to 1900. He ran as Vice President to William McKinley in 1900 and became President in September 1901, when McKinley was assassinated. Reelected in 1904, Roosevelt was President until 1909. A prolific author and naturalist, Roosevelt was instrumental in the Progressive movement of the early twentieth century, helped preserve the nation's natural resources, and extended American power throughout the world with a focus on a modern navy. In 1912, he again sought the Republican nomination for President, but when the convention chose incumbent William Howard Taft, Roosevelt formed the Progressive Party and outpolled Taft in the general election. The Republican division allowed Democrat Woodrow Wilson to win the presidency.

John F. Weston (1845-1917) was born in Kentucky and joined the Union Army's 4th Kentucky Volunteer Cavalry at age 16 in November 1861, although much of his family sided with the Confederacy. Promoted to captain in 1863 and to major in 1864, Weston led a small force to capture Confederate supply boats in Alabama in April 1865. More than three decades later, Weston received the Medal of Honor for these actions. He left the army in August 1865, and began the study of law, but rejoined the regular army in 1867 as a second lieutenant in the 7th U.S. Cavalry. He again gained promotions, rising to the rank of colonel and assistant commissary general on the eve of the Spanish American War in 1898. When the war began, he was commissioned as a brigadier general of volunteers in September 1898, and he served as commissary general at Santiago, Cuba. He returned to the regular army in 1899 and was promoted to brigadier general in 1900. Five years later, he was promoted to the rank of major general and sent to the Philippines, where he was the highest-ranking U.S. Army officer. From January to June 1909, Weston commanded the Department of California before retiring from the U.S. Army in November 1909.

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