Benjamin Colbert was born March 24, 1873, to James Allen Colbert and Athenius Madeline Folsom Colbert at Colbert Station, Indian Territory. He was a descendant of Chickasaw leaders, a friend of U.S. President Theodore Roosevelt and served during Chickasaw Nation Governor Douglas H. Johnston’s administration. Colbert served his country in three wars, two in uniform and one repairing airplanes.

He attended Chickasaw and Choctaw schools and later went to college at Baylor University in Waco, Texas, for a year. While a student at Baylor, he was a member of the boxing team and a sprinter on the track team.

Colbert met President Roosevelt in San Antonio, Texas, May 23, 1898. After an interview with the future president, he enlisted in the First United States Volunteer Cavalry. He became a member of the Rough Riders and soon set sail for Cuba, landing in Daiquirí. He maintained a diary throughout his military service which is now housed at the Oklahoma History Center in Oklahoma City, Oklahoma.

Colbert fought in every battle during the Spanish and American War: Las Guasimas, San Juan Hill (distinguished services) and Santiago. He was also assigned as secretary to Col. Roosevelt.

After the war, Colbert served as secretary to Governor Douglas H. Johnston of the Chickasaw Nation. He was later appointed a member of Governor Johnston’s cabinet and national agent for the Chickasaws. He also fulfilled the role of clerk pro tempore of the Chickasaw Senate in 1899.

In 1902, President Roosevelt selected Colbert as the United States Marshal of the Southern District Indian Territory, making him the youngest marshal ever appointed. After his term as marshal, he returned to Tishomingo, Oklahoma, and later rejoined the military during World War I. He enlisted in machine gun officers training school, where he taught as an instructor.

He was also in a secretary role for State Rep. Ulysses S. Stone from 1928-1938 and lived in Maryland. He later returned to Oklahoma and was employed by Spartan Aeronautics repairing planes used during World War II.