Calico Jack Rackham was a famous English pirate who patrolled the Caribbean Sea from 1718-1720. He got his name from the calico clothes he wore (patterns of brown, white, and black).

Calico Jack became a pirate captain in 1718 while he was aboard a ship operated by Charles Vane. When the ship encountered a French battleship, Vane decided to sail away rather than attack the ship. The crew was outraged, mutinied and left Vane marooned on a distant island. They then made Calico Jack their new captain. Calico Jack proceeded to attack the French battleship, board it, and take everything. That same day, he plundered several other vessels sailing in the Caribbean. In the coming months, he would plunder many vessels off the coast of Jamaica.
Calico Jack is perhaps most famous for his relationship with the female pirate Anne Bonny. The pair met while Calico Jack was drinking at a tavern in the Bahamas. At the time, Jack had accepted an offer from the governor of the Bahamas to cease pirating activities for an unconditional pardon. Jack immediately became smitten with Bonny, even though she was married to another pirate. Bonny's real husband was outraged and demanded that Bonny be publicly flogged. Instead, Calico Jack and Bonny took the sea and resumed pirating activities.

Rackham met his end in 1720 after he and his crew stole an anchored merchant vessel in the Bahamas. The governor, Woodes Rogers, immediately sent two recovery ships with 45 men to capture the pirates. The first of the ships eventually caught up with Calico Jack and engaged the pirate sloop in a sea battle. The pirates proved victorious and subdued most of the crew, except for one man. They spared the man's life when he agreed to help them pirate. The new pirate and Anne Bonny soon became inseparable, which drew the wrath and jealousy of Calico Jack. When Jack finally confronted him, the man admitted to being a woman in disguise! Her name was Mary Read.

Soon, the second recovery ships caught up with Calico Jack and his crew. In the ensuing fight, the pirate ship was severely damaged and Calico Jack and his crew were forced to surrender. On November 20, 1720, Calico Jack and his crew were hanged on an island called Deadman's Cay near Port Royal, Jamaica. Their bodies were chained up and hung at various spots on the island to discourage other would-be pirates. Anne Bonny, who supposedly attended Jack's execution, was reported to have said she was sorry to see him there, but if he had fought like a man, he need not have been hanged like a dog.