Fleetwood was a free man born in Baltimore, Maryland. He traveled to Liberia as a young man and attended Ashmun Institute in Oxford, Pennsylvania. During his life he was an editor, a musician and a government official. He organized a battalion of the District of Columbia National Guard and a Colored High School Cadet Corps. He is the author of a pamphlet entitled, The Negro as a Soldier, in which he wrote,
…it is possible only to indicate in skeleton the worth of the Negro as a solider. If this brief sketch should awaken even a few to interest in his achievements, and one be found willing and fitted to write the history that is their due, that writer shall achieve immortality.