This is a preview for a character to be featured in the Blood & Plunder: Raise the Black kickstarter on October 6. you can check out Raise the Black here!

One of the legendary colorful pirates of the early eighteenth century Caribbean, John “Calico Jack” Rackham has in spite of this only a small provable record of piracies, identical to that of his most famous companion pirates, Anne Bonny and Mary Read. In fact, were it not for his association with these women pirates, he would probably be a mere footnote in pirate history. 

As with many pirates of this era, much of what is reported about him has come from Charles Johnson’s chronicle of pirates, much of which is true and much of which is not—“alleged” is often the best term. From Johnson we learn that Rackham was Charles Vane’s quartermaster during an encounter with a French ship on November 23, 1718, soon after a raucous rendezvous with Blackbeard’s crew. The Frenchman turned out to be a man-of-war rather than a merchantman and did what men-of-war do: it opened fire and gave chase, with Vane wisely choosing the better part of valor. Rackham, however, preferred to fight, but pirate captains having full authority in time of battle, Vane’s order stood. The next day Vane was voted out of his office by the crew and Rackham into it. 

However, Johnson also writes confusingly that the parting came about not after Vane’s refusal to fight, but after an altercation ashore when Rackham commanded the captured merchantman Kingston of London. The pirate crews were in drunken celebration, and Vane asked Rackham for some of his crew’s stock. But Rackham sending too little, the two captains fell out, with Rackham threatening to shoot Vane through the head.

In the version with Rackham in command of the brigantine, he and his crew soon captured several small vessels, then a Madeira-Man (a ship trading to Madeira) off Jamaica, then another small ship and a pink (the English version of a flibot or urqueta—a small flute), after which the pirates careened at a small island and celebrated Christmas. Rackham soon lost the two prizes when they were captured by a pirate hunting sloop sent out by Governor Woodes Rogers. For two months afterward they took no prizes but for a merchantman laden with indentured servants, a ship soon recaptured by an English man-of-war.

For a while Rackham and his crew laid low in a Cuban backwater, then found themselves trapped at anchor by a Spanish guarda-costa. Putting his men in their boats and canoes, Rackham led them away at night, surprised the crew of the guarda-costa’s prize, and made their escape in the vessel. At some point—Johnson’s two Rackham timelines are inconsistent—Rackham heard that war had been declared against Spain, so he and his crew set sail for New Providence and accepted the King’s amnesty. 

However, the contrary timeline has Rackham in the Kingston trapped by two pirate hunting sloops on an island. The sloops recaptured the Kingston but Rackham and his crew escaped ashore and soon set sail aboard a boat, sailed to the Isle of Pines, destroyed some Spanish boats, and set sail in another for New Providence to accept the King’s amnesty.

In any case, here Rackham met Anne Bonny and, after spending his plunder on her, took to sea aboard a privateer commanded by Captain Burgess. The cruise was successful enough that Rackham was able to spend more plunder in his pursuit of Bonny. But his paramour was married, no longer to the seaman she met in Ireland but to James Bonny, a pardoned pirate. Governor Woodes Rogers, hearing that she was cohabiting with Rackham and not her husband, threatened to have her whipped.

Needing to flee, she helped Rackham steal the 12-ton sloop William owned by John Haman, said to be the swiftest around. Dressed as a man, she fled aboard it with Rackham and several others, and reportedly soon afterward was pregnant. The infant was born on the coast of Cuba “where Rackam kept a little kind of a Family,” and was apparently abandoned there, probably to island associates. But again, the timeline is inconsistent, and the story about the child born at Cuba may not be true.

We know little about Rackham’s possible piracies prior to his taking command of Vane’s brigantine, probably the Lark of 12 guns. He may well have sailed with Vane since he first became a pirate, in which case, according to Johnson, Rackham would have been with Vane when he sailed under Henry Jennings and stole the Spanish silver fished up from the sunken treasure ships on the coast of Florida. According to Johnson, Rackham was with Vane when he sent a fireship against Woodes Rogers’s pirate hunting flotilla at New Providence and escaped to sea, and therefore would have been with him during several subsequent piracies until the encounter with the French man-of-war.

At this point we come to the only proven record of his piratical adventures, identical to those of Anne Bonny and Mary Read. It runs only from August into October 1720, all aboard Rackham’s small William with a crew of fewer than a dozen, and is his most famous cruise of all, for here he had Anne Bonny with him at sea, and here Mary Read, a female pirate in disguise, revealed herself as a woman to them. 

But the list of prizes is short: he stole the tiny 12-ton, reportedly swift sloop William from John Ham at New Providence, made it his own, for which he was listed as wanted by Governor Woodes Rogers of New Providence. Turning pirate, he plundered seven small fishing boats at New Providence, a pair of merchant sloops off Hispaniola and another off the Jamaica coast near Port Maria Bay, a canoe off the Jamaica coast, and the Mary & Sarah at Dry Harbor, Jamaica. All of the prizes were small and taken without a fight.

Read, Bonny, Rackham, and the rest of the crew were captured in late October 1720 by merchant captain and commissioned pirate hunter Colonel Jonathan Barnet after his consort, Captain Bonnevis, spotted them at anchor and reported the pirates to Barnet who immediately set sail after them. He chased Rackham and his crew into a moonless night, under which circumstances Rackham was still unable to shake his pursuer—a bad seaman, perhaps, or drunk, or simply not up to Barnet’s sea fighting standard. Rackham reportedly had a very fast vessel, yet Barnet overtook him.

A fight in which only token resistance was offered soon took place. Barnet ordered Rackham to strike to the King’s colors, to which Rackham replied, “We will strike no strikes!” and fired a swivel gun and small arm. Barnet returned fire with a broadside and a volley of small arms. The pirates begged quarter immediately after the pirate hunter’s guns illuminated the dark water below. Rackham’s tiny sloop was too small to have been mounted with great guns (cannon). Its armament was merely one, and probably no more than two, swivel guns, plus small arms—no match for Barnet’s stout armed sloop.

The captured pirates were taken to Port Royal, Jamaica where they were tried on November 16, 1720, found guilty and sentenced to death. Most were hanged at Gallow’s Point, some at Kingston, their bodies then hung in chains at Plumb Point, Bush Key, and Gun Key off Port Royal as warnings to other seamen not to turn pirate. The two women pirates, however, claimed to be pregnant, and their sentences respited pending further investigation.

Reportedly, Mary Read upbraided Rackham and most of the other male crewmembers during the brief fight with Barnet: she “called to those under Deck, to come up and fight like Men, and finding they did not stir, fired her Arms down the Hold amongst them, killing one, and wounding others.” However, there is no record of dead or wounded among Rackham’s crew. Likewise, Anne Bonny’s reputed words to Rackham just before he was hanged: that she “was sorry to fee him there but if he had fought like a Man, he need not have been hang’d like a Dog.”

Legends like these have remained with John Rackham. Yet even his nickname, Calico Jack, derived from his reputed practice of wearing “jackets and drawers made of calico,” may be fictional. As for the famous pirate flag of skull and crossed swords attributed to him and used in many pirate films, it is a twentieth century invention, probably based on the flag used by Captain Blood in the 1935 film of the same name starring Errol Flynn. The only known flag flown by Rackham as a pirate captain was a white flag, probably intended as French. Under Vane he sailed under an unknown “black flag.”

Like many pirates of this era, Rackham’s legend probably far outshines his reality. Hollywood has seized upon and enlarged his piratical escapades—for which he has Anne Bonny and Mary Read to thank.