Calico Jack, and the Pirate Women Who Defied the Gallows

“Calico” Jack Rackham: Pirate, Lover, and the Gallows

In Port Royal’s history, John Rackham – better known as “Calico Jack” – is less remembered for the loot he stole than for the company he kept. Rackham earned his nickname from his flashy preference for calico-patterned bright clothing. a dandyish flair that set him apart from his swarthier peers. Born around 1682 in England, Rackham was active by 1718 as quartermaster on Charles Vane’s crew. In fact, it was Calico Jack Rackham who led the mutiny that ousted Vane from command, after Vane fled from the French warship. With the crew’s backing, Rackham assumed captaincy of the pirate sloop – an opportunistic rise to power by overthrowing his own captain.

As a captain, Calico Jack proved a somewhat mediocre pirate in terms of plunder seized; he did not capture any massive prizes nor terrorize the seas on the scale of Blackbeard or Morgan. His fame today instead rests on two factors: the design of his flag and the two infamous female pirates in his crew. Rackham’s Jolly Roger flag – a skull with crossed swords – has become one of the iconic pirate symbols often attributed to him, representing his swashbuckling persona. More significantly, Rackham recruited (albeit unknowingly at first) Anne Bonny and Mary Read, two women who concealed their gender and fought alongside his men. Their presence made Rackham’s crew unique and scandalous in the eyes of the public, and their ferocity in battle would ensure that Calico Jack’s tale endured in legend.

Rackham’s most notable exploits took place in 1720 in the waters around Jamaica and the Bahamas. For a time, he actually accepted a royal pardon and gave up piracy, residing in the British-controlled island of New Providence. It was there he met Anne Bonny, and failing to win the governor’s permission to court her (she was another man’s wife), Jack threw in his lot with Anne and returned to piracy. In August 1720, Rackham, Bonny, and a small crew (including Mary Read, who joined disguised as a man) stole a sloop and embarked on a brief piratical spree. They captured a handful of small merchant vessels around Jamaica’s coast, with Anne and Mary reportedly fighting as fiercely as any man during these raids. Their luck ran out one moonless night in October 1720.

Calico Jack’s sloop was anchored off Point Negril, Jamaica, and the crew was deep in drunken celebration of recent loot. Near midnight on October 22, 1720, a shadowy vessel glided up alongside them – a royal schooner sent by Governor Nicholas Lawes and commanded by Captain Jonathan Barnet. In the dark, Barnet’s forces caught Rackham’s pirates unprepared. Anne Bonny and Mary Read, likely the most clear-headed on deck, raised the alarm and prepared to fight, cursing at their slumbering crewmates to wake up. Rackham and a few others stumbled up to make a stand, but most of the pirates were too inebriated to resist.

As Barnet’s men opened fire, Calico Jack Rackham soon signaled surrender rather than be blasted to pieces. However, Anne and Mary refused to surrender so tamely. They fought on fiercely, shooting and slashing at the attackers even as their comrades cowered below decks. According to legend, Mary Read was so disgusted at the men’s cowardice that she leaned over the hatch and yelled, “If there’s a man among ye, come up and fight like the man ye pretend to be!” – punctuating her challenge with a pistol shot down into the hold, killing one of the shirkers. Such was the ferocity of the two women that it took Barnet’s full force to finally subdue them and capture the crew alive.

Brought to Jamaica for trial, Rackham and his men were swiftly convicted of piracy. Jack Rackham was hanged in Port Royal on November 18, 1720. still only in his thirties. As a final token of admonition to would-be pirates, the authorities gibbeted his body in an iron cage and suspended it on a small islet at the harbor’s entrance. That spot has since been known as Rackham’s Cay, where the skeletal remains of “Calico Jack” swung as a grim warning to his brethren. A poignant footnote: before his execution, Rackham was allowed one last meeting with Anne Bonny. Rather than words of love, Anne reportedly gave him a scathing farewell: “Had you fought like a man, you need not have been hanged like a dog.” It was a brutal final reproach from a woman who had shared his crimes but not his surrender.

Anne Bonny and Mary Read, being women, drew intense public curiosity at their trial. Both pleaded their bellies – claiming to be pregnant – which under British law won them a temporary stay of execution. Indeed, it was confirmed both were expecting, likely by lovers among the crew. Mary Read, alas, fell ill while imprisoned in Spanish Town and died of fever in April 1721 before childbirth. She was in her mid-20s at the time.

Anne Bonny’s fate is more mysterious. There is no record of her execution ever taking place. Most evidence suggests her influential father quietly secured her release from prison. One account has Anne returning to her father in Carolina and living out a long life under a new name, reportedly dying peacefully in her 80s. Other folklore claims she moved to England or even to Louisiana, but in any case, Anne Bonny disappears from official records after 1721. Thus, the “pirate queen” who had briefly terrorized the Caribbean simply faded into genteel obscurity – a rare pirate who might have escaped the hangman and lived to old age.

What is certain is that Anne Bonny and Mary Read became legendary. In an age when women were expected to stay ashore, these two donned trousers, took up cutlass and pistol, and fought shoulder-to-shoulder with male pirates. Contemporary descriptions called them “fierce hellcats” whose rage in battle was unmatched. Their story has inspired countless books and tales, forever linking their names to Calico Jack Rackham’s legacy. It was due to their infamy that Rackham’s exploits were remembered at all – as one historian quipped, “Jack’s reputation survived primarily because of the two notorious women in his crew.” Together, the trio of Rackham, Bonny, and Read form an unforgettable chapter of Port Royal’s pirate history, encapsulating the rebellious spirit and intrigue that continue to fascinate us about that era.