3 x 4 1/8 in. oval portrait on cardstock mount with Holloway's embossed imprint on recto along with calligraphic inscription beneath image reading: "Richard S. Winslow. Co. h., 54th Regt., Mass. Vols. 1863-4-5. Verso bears identical inscription in a different hand along with modern pencil inscriptions including one indicating the subject may have belonged to "GAR Post 83, South Short, MA."

An attractive post-war portrait of Winslow, who enlisted on 10 December 1863, as a private in the 54th Massachusetts Volunteers, the famed African American regiment. He served through the end of the war, seeing action at the Battle of Grimball's Landing and, most notably, the Second Battle of Fort Wagner, where commander Colonel Robert Gould Shaw lost his life. Winslow sustained an accidental wound to his foot at Sumter, SC, on 10 April 1865, but continued serving with the 54th until September of 1865.