Calico Jack Rackham is remembered more for his favorite clothing and his female crewmembers than for his mediocre accomplishments as a pirate. His nickname- Calico Jack is for the cheap and brightly colored cotton clothes he was fond of.
One of the first references to him finds him as quartermaster for Charles Vane's operation out of New Providence, Bahamas in 1718. Late that year, Vane fired on a French vessel that he then discovered was a warship. Although he felt discretion and retreat was the better part of valor, his crew disagreed, and the next day he was sent off after Calico Jack was elected captain.
He spent several months cruising the Caribbean, having as much success in attacking smaller vessels that his little sloop would allow. One story claims it was because his ship the Kingston was retaken by its owner in Jamaica that he decided to stop being a pirate. In late spring of 1719, Rackham returned to New Providence and received a pardon from Woodes Rogers.
Perhaps he merely chose a poor place to swear off piracy, but when he began an affair with Buy Flag (more info) Anne Bonny, the pardon was soon forgotten. They had a baby that was eventually left in the care of some pirate families in Cuba, and Jack Rackham returned to his former ways, stealing the sloop Curlew and taking Bonny along, dressed as a man. Bonny's husband James may have gone with them, since he was a poor sailor seeking the wealth of a pirate's life. Some claim he was too intent on punishing his wife for her affair.
The odd bunch spent over a year attacking small vessels around the West Indies and took on a sailor that would later prove to be a woman named Mary Read . Calico Jack at first confronted the 'man' who was spending too much time around Anne, but later relented upon discovering her identity and realizing the benefit of friendship for the pair.
Calico Jack Rackham's run came to an end around October 1720, after Woodes Rogers found out about his return to piracy. A government sloop led by Captain Barnet caught up with him at the west end of Jamaica while the crew was drunk and/or asleep and unable to fight. The women tried to sail the ship away, but it was soon overtaken. Read, Bonny, and one man were said to be the only fighters, shooting into the hold to try and rouse the others from their hiding spot. Their shots wounded one and killed another.
The entire crew was soon arrested and taken to Jamaica to be tried for piracy. The proceedings caused quite a stir because of the women pirates, but the women themselves escaped the noose because of pregnancy. The rest of them were hung on November 27, 1720. Calico Jack's body was gibbeted and hung as a deterrent on Deadman's Cay near Port Royal.