When Anthony T. Buckner (1845-1923) died, the Daily Progress, Charlottesville's white newspaper, published his obituary on the front page, a rare distinction for a Black man.

He had been born into slavery in Spotsylvania County, Virginia. By the time he commissioned this portrait of himself and his granddaughter, Eileen Buckner (1909-1985), he had become one of the most respected merchants in the city.

His son, George W. Buckner, who was Eileen's father, wrote the New Negro manifesto that was published in the Charlottesville Messenger in 1921.