Calico Jack Rackham was a flamboyant pirate and no ordinary jack would have suited his purpose. He devised a jack which consisted of a skull with crossed cutlasses on a black background. But in the end he he was boarded without a shot. Anne Bonny, his lover and one of his crew was sickened by this act of cowardice that when Rackham was to be hanged, She could only comfort him by saying, "If you would have fought like a man you needn't die like a dog."

Calico Jack's flag was resurrected by Hollywood for the movies "Cutthroat Island" and "Pirates of the Caribbean: Curse of the Black Pearl".