After leaving Vane marooned, Calico Jack and the crew captured a merchant ship The Kingston, which had a rich cargo and would have kept him and the crew in funds for months. However he was only off the coast of Port Royal when he took the ship and the merchants who had cargo on it quickly hired a bunch of bounty hunters to sail after him. They pursued him all the way to Isla de los Pinos off Cuba and while Jack and his crew were ashore the bounty hunters recaptured the The Kingston and took it back to Port Royal.
Somehow Rackham and his men made it back to Nassau where he met with Governor Rogers and accepted the Royal Pardon to all pirates that was still on offer, claiming that Vane had forced him into piracy.
Whilst in Nassau Calico Jack met Anne Bonny who was married to John bonny a former pirate who had turned informer. Jack appealed to Governor Rogers to annul Anne's marriage, but he refused. They continued their relationship and when Anne became pregnant Jack sent her to Cuba to have the baby. While Anne was away Jack met up with Mary Read, who dressed as a man and had also been a pirate before accepting the pardon.
Shore life did not suit Jack and in August 1720, Jack, Bonny, Read, and a number of other pirates made off with a ship under cover over darkness. They resumed their piratical career but for some reason they never took any big prizes preferring to concentrate on small fishing vessels and poorly armed merchant ships.
Their renewed career was short. Four months later at the end of October his ship was caught by Captain Barnet a bounty hunter who patrolled the Caribbean. The popular story is that Jack and the male members of the crew fled below decks while Bonny and Read fought. The crew were captured and taken back to Jamaica for trial.
The trial was a forgone conclusion and the crew were sentenced to death, Bonny and Read were spared the noose because they were both pregnant. A popular story is that Bonny was allowed to see Jack one last time before he was hanged, but it was not a warm meeting as she is supposed to have said “I'm sorry to see you here, but if you had fought like a man, you need not have hanged like a dog."
Calico Jack life ended in the hangman's noose on November 18 1720. Like many pirates before him his body was left to rot in a gibbet in the harbour.
Given Calico Jack's lack of success as a pirate it is likely that he would not have been more than a footnote in history were it not for the two women pirates in his crew.