The 4th U.S. Colored Infantry was organized in Baltimore in July 1863, and Fleetwood, a publisher, became the regiment’s sergeant major. On September 29, 1864, at Chaffin’s Farm on the outskirts of Richmond, Va., the regiment charged a Confederate position with Fleetwood leading on the left flank. When two of the color bearers went down, he grabbed the American flag and carried it to the end of the battle. He received the Medal of Honor for his actions.