John “Calico Jack” Rackham – Caribbean Pirate
John “Calico Jack” Rackham (1682-1720), a name synonymous with the Golden Age of Piracy, remains an intriguing figure in the annals of maritime history. Known primarily as “Calico Jack” due to his penchant for flamboyant clothing made from colorful calico fabric, Rackham carved out a notorious career as an English pirate captain. His area of operations centered on the waters surrounding the Bahamas and Cuba during the peak of pirate activity between 1650 and 1730. Born in England on December 26, 1682, the details of his early life remain shrouded in mystery, with the historical record only picking up his trail as he made his way to the New World in the early 18th century.
The earliest documented evidence of John “Calico Jack” Rackham places him aboard the sloop Ranger in 1718, serving as quartermaster under the command of Captain Charles Vane. The Ranger‘s crew operated primarily out of New Providence Island in the Bahamas, a haven for pirates so notorious that it earned the moniker "Pirates’ Republic." This island served as a base for countless buccaneers, offering a safe harbor and a strategic location from which to launch raids on passing merchant vessels. The atmosphere of lawlessness and opportunity fostered a thriving pirate community, making New Providence a pivotal location in the history of Caribbean piracy.
The Ranger‘s exploits led them north, where they targeted and plundered several ships off the coast of New York City. This series of successful raids brought them considerable wealth and notoriety, but their luck was soon to be tested. During one such excursion, the Ranger encountered a formidable French man-of-war, a heavily armed and well-manned warship significantly larger than their own vessel. The French ship, at least twice the size of the Ranger, immediately gave chase, presenting the pirates with a difficult decision: fight or flee.
Captain Vane, assessing the overwhelming advantage of the French vessel, ordered a retreat. However, this decision was met with strong opposition from John “Calico Jack” Rackham. Rackham, ever the bold and audacious pirate, argued vehemently in favor of engaging the larger ship, reasoning that it would likely be laden with valuable treasure and that victory would result in the acquisition of a superior vessel. He rallied support for his position, believing that the potential rewards outweighed the risks.
Despite Rackham’s persuasive arguments, Vane remained steadfast in his decision to retreat. He asserted his authority as captain, emphasizing that his command was final. A vote was taken among the crew, revealing a significant divide: only 15 men supported Vane’s decision, while the remaining 75 sided with Calico Jack’s call to arms. However, Vane invoked his prerogative as captain, overruling the overwhelming majority and ordering the Ranger to flee the approaching French man-of-war. This act of perceived cowardice would have significant consequences for Vane’s leadership.
The incident fueled discontent and resentment among the crew, who felt that Vane had squandered an opportunity for significant gain and had acted against the best interests of the pirate enterprise. The seeds of mutiny had been sown, and it was only a matter of time before the simmering tensions boiled over. The affair was far from over, and Calico Jack would soon seize the opportunity to challenge Vane’s authority and take command of the Ranger.
On November 24, 1718, Calico Jack openly challenged Captain Vane’s leadership. He publicly branded Vane as a coward, citing his refusal to engage the French man-of-war as evidence of his unsuitability to command. Rackham then called for a vote among the crew to determine whether they agreed with his assessment and wished to remove Vane from his position. The vote was overwhelmingly in Rackham’s favor, signaling a decisive rejection of Vane’s leadership. The pirates, emboldened by Rackham’s courage and their own dissatisfaction, voted overwhelmingly to remove Vane from the captaincy, paving the way for Rackham to assume command.
With Vane deposed, John “Calico Jack” Rackham was elected as the new captain of the Ranger. The crew, now under Rackham’s leadership, wasted no time in dispensing with their former captain and his loyalists. Vane and his 15 supporters were cast adrift in a smaller boat, provided with a meager supply of ammunition and goods, effectively marooning them and leaving them to fend for themselves. This act solidified Rackham’s authority and signaled a new era for the Ranger and its crew.
Under Rackham’s command, the Ranger embarked on a campaign of piracy throughout the West Indies and the waters near Bermuda. They focused on plundering smaller vessels operating close to the shore, amassing wealth and supplies through these opportunistic raids. In December of the same year, Rackham and his crew captured a Jamaican merchant ship named the Kingston. This vessel was laden with a rich cargo, making it a highly prized acquisition for the pirates. The crew decided to make the Kingston their new flagship, reflecting its superior size and potential for future plunder.
However, their success was short-lived. The capture of the Kingston had not gone unnoticed, and the outraged merchants of Port Royal, Jamaica, responded swiftly. They hired bounty hunters to track down the pirates and retrieve their stolen goods. The bounty hunters eventually caught up with the Kingston as it lay anchored off the coast of Cuba in February 1719. The pirates, having gone ashore, were caught off guard and forced to flee into the woods, abandoning their newly acquired flagship and its valuable cargo. This marked a significant setback for Rackham and his crew, forcing them to regroup and seek new opportunities.
Following the loss of the Kingston, Calico Jack and his crew made their way to Nassau in the Bahamas. Unbeknownst to them, the political landscape of the Bahamas had undergone a significant change. British Governor Woodes Rogers had been dispatched to address the rampant piracy problem and restore order to the region. Rogers offered a general amnesty and royal pardon to any pirate willing to renounce their illegal activities in exchange for forgiveness.
Captain Jack and his crew, facing dwindling resources and uncertain prospects, decided to accept Rogers’ offer. They claimed that Captain Charles Vane had coerced them into piracy, a convenient excuse that allowed them to portray themselves as victims of circumstance. Rogers, harboring a deep animosity towards Vane, granted the pardon, effectively absolving Rackham and his crew of their past crimes. Rackham subsequently relocated to New Providence, hoping to start a new life.
While in New Providence, Rackham frequented the local taverns, where he met Anne Bonny. Despite being married to James Bonny, a sailor and government informant, Anne and Rackham began a passionate affair. When James Bonny discovered their relationship, Rackham offered to pay him for a divorce, a common practice at the time. However, James Bonny refused, setting the stage for further complications.
Driven by their love for each other and a shared desire for adventure, Rackham and Bonny, along with a new crew, stole a sloop and returned to piracy in August 1720, effectively voiding Rackham’s pardon. Rackham’s decision to have Bonny accompany him was considered highly unusual, as women were generally believed to bring bad luck aboard ships. They then sailed the Caribbean for several months, seizing other pirate ships and frequently inviting crew members from other ships to join their ranks. Bonny did not conceal her gender from her shipmates, but when engaging in pillaging, she disguised herself as a man and participated in armed conflict.
Before long, Anne became pregnant and gave birth to a son in Cuba. What became of the boy remains unknown. Bonny quickly returned to the pirate life.
At some point during their piratical escapades, another woman, Mary Read, joined Rackham’s crew. Read often disguised herself as a man, adding another layer of intrigue to the already unconventional pirate band.
In September 1720, Governor Rogers issued a proclamation declaring that Rackham and his crew had resumed their piratical activities. Soon after, a pirate hunter named Jonathan Barnet began searching for Calico Jack. Cruising along the coastline near Jamaica, Rackham and his crew had captured a number of small vessels, word of which soon reached Barnet.
Under a commission from Nicholas Lawes, the Governor of Jamaica, Barnet and his crew launched a surprise attack on Rackham’s anchored ship, the William. Most of Rackham’s pirates offered little resistance, as they were heavily intoxicated from celebrating their recent capture of a Spanish commercial ship. However, Read and Bonny fought fiercely, holding off Barnet’s troops for a short time. In the end, the women were overwhelmed, and Rackham and his crew were taken to Jamaica to stand before the court. The presence of female pirates in the crew caused a sensation.
Captain Jack and the male members of his crew were tried on November 16, 1720, and sentenced to hang. Anne was allowed to visit Rackham one last time before his execution, but rather than consoling him, she reportedly said: "Had you fought like a man, you need not have been hanged like a dog."
Anne and Mary were tried a week after Rackham and his men were executed. After being convicted, Read and Bonny both "pleaded their bellies", asking for mercy because they were pregnant. In accordance with English common law, both women received a temporary stay of execution until they gave birth. Mary Read died in prison from fever in 1721, but the fate of Anne Bonny remains unknown.
Though there are no records of Bonny’s release or execution, it is said that her father bought her freedom from Jamaican Governor Lawes and she returned to Charleston, where she gave birth to Rackham’s child.
Though Calico Jack was relatively a small-time pirate, his legacy received fame for two reasons, the first being the fact that he sailed with female pirates. The second is that his iconic flag, displaying a skull and crossbones, came to represent piracy itself, although there is no proof he ever flew a flag like it.