Reggie Gammon's Naval Trainee was painted when Gammon himself was a naval trainee at Camp Shoemaker, California, in 1944. A small group of these thoughtful portraits survive, and they are notable records documenting men who served in the still-segregated US armed forces of the 1940s.

Gammon paints a sensitive, introspective likeness of his unnamed sitter, who looks away from us, lost in thought. Gammon grew up in Philadelphia and previously worked with Dox Thrash at Sun Shipbuilding in Chester, PA, before enlisting in the Navy. At Sun, one of the largest employers during WW II, dry dock #4 was created after protests from African Americans denied jobs at Philadelphia's Navy Yard. The segregated dry dock built 54 ships for the war effort and trained its workers to become skilled shipbuilders.