John Rackham, better known as Calico Jack (1682 – 1720), is one of the best-known pirates of the Golden Age of Piracy, not because he was particularly successful or much good at being a pirate – compared to other famous pirates, his career was middling and his accomplishments mediocre – but because of his associations with other, more successful pirates, his venality and backstabbing which stood out even in a profession built on venality and backstabbing, because his first mate designed the Jolly Roger flag, and because his crew included two famous female pirates, Anne Bonney and Mary Read.
Nicknamed Calico Jack because of the colorful calico clothes he favored, Rackham was quartermaster aboard the pirate sloop Ranger in 1718, when she encountered a French man of war twice her size, and the pirate captain, choosing discretion over valor, fled. Rackham and the crew decried what they viewed as cowardice, and soon thereafter voted the captain out of the command, and replaced him with Calico Jack.
As captain, Rackham specialized in plundering small vessels engaged in coastal trade but fell upon larger ships when the opportunity presented itself. In 1719, he accepted a royal pardon, renounced piracy, and accepted a commission from the governor of the Bahamas to hunt pirates. However, a love triangle involving Anne Bonney, the future pirate, grew complicated and ended with the Rackham and Bonney stealing a sloop to slip out of the Bahamas, thus voiding Rackham’s recent pardon.
In October of 1720, a pirate hunter chanced upon Rackham’s ship at anchor, while Calico Jack and most of his men were too drunk to offer effective resistance. The only fight was made by the women, Anne Bonney and Mary Read, who offered fierce resistance before they were finally subdued. Captured, Calico Jack was tried and convicted of piracy and sentenced to death by hanging.
His lover, spared the noose after “pleading her belly” – she was pregnant – had little sympathy for him, and when he grew maudlin while bidding her goodbye before his execution, she reportedly sneered: “if you had fought like a man, you would not hang now like a dog!” He was hanged on November 18th, 1720, and his corpse was displayed from a gibbet at the entrance to Port Royal, Jamaica, in an inlet known thereafter as Rackham’s Cay.