At twenty-five years old, Michael Stewart was a young Black aspiring artist, deejay, and model, looking to make a name for himself in the vibrant downtown art scene of early 1980’s New York City.

Jean-Michel Basquiat’s The Italian Version of Popeye Has No Pork in His Diet, 1982—which has been out of public view for almost two decades—is headed to auction next month and is estimated ...