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Calico Jack

(Pirate Captain)

John Rackham, commonly known as Calico Jack, is perhaps one of the most hyped of all pirates. The Story of Calico Jack has been retold many times but few people see the similarities of Calico Jack's story and the oft’ remade Hollywood movie "A Star is Born". So let me fill in the blanks for you.

Calico Jack Rackham

Calico Jack Rackham

Calico Jack was not as successful as Morgan or Roberts nor as ruthless as Nau or Black Beard. Rackham owed his nickname to the fancy shirts he wore. The shirts were colorful calico shirts and thus he was known in the Bahamas and later throughout the pirate world as Calico Jack. However his shirts would not have been enough to make him anything more than a foot note in pirate lore. Rackham had two things going for him that ensured he would be known as more than a well dressed pirate; Rackham had Anne Bonny and Mary Read.

There are two accounts of how Jack Rackham became “Captain Calico Jack Rackham”.

One account has him quartermaster on a British Man-O-War, the Neptune sailing under a Captain Hywell Vane. The other account has him as quartermaster under the pirate Captain Charles Vane sailing on the Treasure. In both accounts Captain Vane (take your pick) chickens out when it comes to taking on French man-o-war and Rackham incites a mutiny and, with the captain deposed leads a successful attack on the French ship.

Details of the pirate Vane and the Calico Jack’s life suggest that Jack Rackham probably was not the mutineer that put Charles Vane adrift. We know from most historical accounts that Charles Vane left Barbados in 1718 and headed to New York. From New York he set off plundering ships as he headed back to the Caribbean. Sometime after this, he his crew deposed him, his supporters being given a smaller sloop to go their own way.

It is at this point the most accounts mention his quartermaster being Calico Jack. Unfortunately this doesn’t make sense when you consider Calico Jack started off pirating with Anne Bonny at about this same time and Bonny was not a member of Vane's crew.

It is more likely that Rackham committed his mutinous act against Hywell Vane and then turned to piracy before 1717. In 1717, Jack Rackham sails from Jamaica to the Bahamas and accepts Wooded Rogers pardon. At this same time, Charles Vane refused Roger’s pardon and goes on the account. Had Rackham gone off with Vane he could not have been making time with Anne in the Bahamas because Vane had set off for Barbados, and New York!

Calico Jack and Anne Bonny

We know that Calico Jack met Anne Bonny in the Bahamas around 1717 or 1718 and tried to buy her from her husband James Bonny, a two bit smuggler. James Bonny took the matter up with Governor Woodes Rogers who saw this as a good reason to flog young Anne. The Governor threatening to flog Anne was good enough reason for Calico Jack and Anne find a friendlier climate. It is at this point that Calico Jack decides to as Woodes Rogers so delicately put it,“return like a dog to the vomit”, that is, turn pirate again.

Some sources claim Anne's sex was hidden from the crew but evidence suggests that she was well known in New Providence, especially by associates of Calico Jack, who evidently made up the rest of his crew on the Revenge. Shortly after taking to the sea, Jack came upon a ship and captured it. As was the custom of the day, the captured crew was asked who among them would sign articles and join the Revenge. Among those who agreed to sign up was an especially skilled swordsman who had impressed Calico Jack and Anne.

Against all odds, it turned out that this magnificent swordsman was also a woman, Mary Read. Mary Read divulged her secret to Anne and after Rackham became jealous of the time Anne was spending with her and threatened to kill both of them, the two women decided to let Jack in on the secret. Apparently Jack had a big mouth and before you know it the whole crew knew.

The Revenge and her flamboyant captain quickly became quite the terror of the Caribbean much to the chagrin of Woodes Rogers, who began recruiting former pirates to act as pirate hunters. Among the most ferocious of his crew were the two women. We know from the historical accounts that several ships were attacked by Rackham and the women fought openly as women and were the most violent of the crew. It wasn’t long before all the Caribbean was abuzz about stories of a pirate ship with two fearless female pirates aboard. The imaginations of the time ran wild. Almost as wild as imaginations today!

Some sources claim that as Anne and Mary became more popular with the crew and their notoriety spread, Calico Jack became despondent and took to rum. Eventually even the crew started looking toward Anne and Mary as the real captains. Are you seeing the “Star is Born” theme?

Capture and death

Whatever the case, Jack’s days were numbered and by 1720 his short career came to an end as the Pirate Hunter Barnet caught up with him. He and his crew were drunk at the time. They put up a bit of fight but when their main mast was shot away and there was no hope of escape it claimed they went below deck and did what any self respecting pirate would do. They finished off the rum, knowing it would be the last rum they would get.

Jack and his crew were tried at St. Jago de la Vega in Jamaica where they were promptly found guilty and sentenced to hang. Calico Jack was granted a last request to see Anne one more time before being hanged. She promptly rebuked him by saying "I'm sorry to see you here, but if you'd have fought like a man you needn't hang like a dog.” He was hanged on November 17, 1720 and then displayed in chains at the spot now known as Rackham’s Point in Jamaica.

Thus ended the career of a rising star that was surpassed in the history books by his greatest discoveries — Anne Bonny and Mary Read!

Too bad about Jack but that is that!
A really smart dresser with a really nice hat.
Had he kept to Code with no lassies aboard
He might not a hanged by the sea on the shore.

Profile picture for user Tobias Gibson

The only author and editor of all pages on the site. Most of what I write about is based on years of book reading on the topic. My first web page was published back in 1994.

Updated: 04 September 2022