John Gotti was a famous mobster from the Gambino crime family. Charged with murder, loansharking, racketeering, obstruction of justice, illegal gambling, tax evasion and more, he was, and is, the most infamous member of the Mafia. Andy Warhol had been known for his portraits at the time and caught the attention of Time magazine in 1986, which was dedicating a cover to Gotti in their “Mafia on Trial” September issue. It was during this time that Gotti had been arrested and was standing trial for racketeering, for which he was acquitted. Six years later, he was charged for murder and sentenced to life in prison without parole. Warhol was known for creating portraits of the beautiful and glamorous, but when Time magazine commissioned him to make this cover, he had a new type of subject to add to his portfolio. Although Gotti did not fit into Warhol’s usual movie star-musician-artist circle, he did possess some of the attributes that Warhol loved about celebrity life. Gotti was known as “Dapper Don” because of his personality in front of news cameras and his expensive clothing. He was glamorous in his own right, and a celebrity in his crime driven world, the public knew John Gotti’s name.