Known as John Rackham, Jack Rackham, and Calico Jack, he was one of the most famous pirates to sail the seas. The name 'Calico Jack' derives from his bright, fine clothing that he often wore.
He originally served as a crew member for a pirate named Charles Vane, but Vane was eventually mutinied upon and Rackham became the new captain. He made quite a name for himself as a pirate in the waters, but he is most notably known for his two female lieutenants: Anne Bonny and Mary Read.
He fell in love with Anne Bonny before their pirate-partnership. He is said to have used a great deal of the plunder he took as gifts for her. But when their affair became public and the Governer threatened their happiness, Jack and Anne managed to assemble a crew and escape out to see. Afraid that the other men would not do well sailing with a woman on board, Anne disguised herself as a fan and fought with them in combat much of the time. Anne began spending a lot of her time with another crewman which obviously filled Jack with quite a bit of jealousy. However, upon pressing the matter he found that the sailor Anne had become so close with was actually another woman disguised as a man who had joined the crew, named Mary Read. Anne had apparently spotted her right from the off. It is said that the women were likely a lot more fierce and outgoing when compared to Calico Jack.
In October of 1720 however, it all came to an end when their ship was attacked in the dead of night. All the men, Jack included, were mostly drunk and asleep and were easily overtaken. It is said that Anne and Mary were the only two who put up a real fight.
Jack and his crew were tried and hanged. Mary and Anne were both spared from this fate claiming to be pregnant, and were thrown in prison. Mary would die in the prison, though the cause is still disputed between either a deadly fever or childbirth. Anne disappeared from record completely and is believed by many to have been ransomed out of jail by a relation.