Pirate Captain Jack Rackham: The Life and Times of Calico Jack, Who Sailed the West Indies

A woodcut of Rackham from Charles Johnson's 1725 edition of A General History of the Pyrates

Jack Rackham was a gentleman pirate with flamboyant fashion sense and a way with female pirates who were dressed like men– notably, Anne Bonny and Mary Read.

Ahoy There. I´m Captain Jack Rackham, and I´m Twice the Dandy You Are

Though perhaps best known for his association with female pirates Anne Bonny and Mary Read, Jack Rackham´s exploits merit more than a passing consideration. He stood out for the flamboyant finery he wore — the name “Calico Jack” came from his tendency to dress in calico coats and britches– and he was also known for his innovative Jolly Roger design that he flew. More significantly for pirate afficionados, he did manage to plunder his fair share of shipping prizes.

Rackham´s early pirate career usually begins with a mention of pirate-captain Charles Vane, aboard whose ship the Treasure Rackham sailed as quartermaster in 1718 in the Caribbean. It was in that year that Vane, fresh from a week-long pirate party in Carolina with Blackbeard and other pirate notables, encountered a French warship and, after a brief exchange of fire, withdrew as cautious pirates concerned about keeping their skin have a habit of doing. This action was enough for the crew to decide that Vane was, to them, a gutless captain in need of a suitable replacement. The replacement came in the form of quartermaster Jack Rackham, who was elected to the post on the following day by the mutineers.

Vane, probably with foaming mouth, and his remaining followers were lowered down into a small sloop and sent on their merry way.

The seas were now open to Calico Jack. Before you could say “Shiver me timbers,” Rackham was off to Jamaica and the surrounding area for a little “don´t mind if I do” plundering spree. Unlike the more ambitious Henry Morgan or Captain Kidd, Rackham´s preference was to attack local merchants and fishing ships, thereby foregoing the richer but more well-defended targets.

Please, Sir. I´ve Sworn off Murdering and Pillaging. Could I Have a Royal Pardon Now?

The year 1719 found Rackham sailing to the Bahamas, where he decided to hang up his pirate cutlass and settle down. He asked for a pardon and received it. Here he happened to meet Anne Bonny at a local tavern where no respectable woman had any business being, especially if she was married, which Bonny was at the time.

Wait a Minute. On Second Thought, Maybe I Was Right the First Time, and a Pirating Life is Really the Only Life for Me

Bonny became pregnant by Rackham and gave birth to a girl. Finding themselves inconvenienced by a lack of money, Rackham again conceived of the notion of taking to the sea and carrying out acts of piracy. This time he took Bonny, disguised as a man, with him. Using the stolen sloop William, Rackham returned to what he knew best–raiding small merchant ships — in his old stomping ground in the West Indies.

It was during this pirating stint that a privateering sloop commanded by Captain Jonathan Barret came upon the William anchored near Nigril Bay in early October, 1720. When Barret´s crew boarded the William, it was essentially Anne Bonny and Mary Read against the world. The remainder of the crew was down below in a drunken, non-fighting condition.

Arrrr. I Need a Sugardaddy and I Need One Quick

Jack Rackham, along with eleven other crewmen, was hanged on November 16, 1720, in St. Jago de la Vega, Jamaica. As for the fate of the two women pirates, Read died while in prison and Bonny, thanks to her rich sugardaddy father, was quietly able to secure her release.