Calico Jack: The Worst Pirate

**Sanitized Transcript:**

What do you think of when you think of pirates? Do you conjure up images of fearless sea dwellers cruising the high seas? Perhaps you think of the more violent realities – two ships locked side by side, their crews crossing swords, their captains dueling to the end. Maybe you even imagine the rugged pirate who’s been marooned on an island, biding his time before he unleashes a bold escape plan.

How long before you think of Blackbeard? Captain Kidd? Black Bart Roberts? Those men were exceptional pirates who used cunning and charm to rob the Caribbean during the height of piracy. History has made them exemplars of the Golden Age of Piracy.

Beyond the top-rate pirates, somewhere down the line, you’ll find the Englishman born under the name John Rackham, immortalized by his pirate moniker, Calico Jack.

**The Pirate Republic**

The Golden Age of Piracy was well underway when Mr. Rackham first appeared in another man’s spyglass. This was the “Classical” age of pirates, where rogues sailed the seven seas and robbed the rich coffers of Spanish, French, and English ships and colonies. It lasted around 80 years, from roughly 1650 to 1730. Every great epoch needs a cultural center, and for the pirates, that was Nassau.

Decades before loyalist settlers escaped the American Revolution by fleeing to the Bahamas, Nassau became an overnight pirate haven, with rogues of all kinds fleeing unfriendly ports to congregate on one massive, pirate-friendly island. Even though it only became a pirate port around 1715 – just a few short years before the end of the Age – Nassau would represent the pirate way of life better than any other ship, cove, or port.

Pirates were a curious lot. They spent their days relieving hard-working merchants of their wares and wasted their nights trying to drink all the rum in the western hemisphere. You’d be forgiven for thinking that these brigands were just Caribbean Vikings with bigger ships and curved swords, but in between all the violence and swashbuckling, pirates could be surprisingly progressive. Many of the pirates that set anchor off Nassau were once soldiers or merchants for one Crown or another, and the system chewed them up and spit them out. They were decommissioned, unprotected, or otherwise abandoned by their government, so they turned to a way of life that promised independence and self-sufficiency.

Nassau and the crews that operated there became something of a strange democracy, where men who were committed to the pirate’s anti-establishment code always had a place to stay and a voice to share. In the early 18th century, the voices that carried loudest often came from men whose names survived the ensuing centuries: Charles Vane, Samuel Bellamy, Benjamin Hornigold, Edward England. John Rackham was not one of these men. He was a lesser-known pirate at best, working as the quartermaster for Charles Vane’s crew.

Rackham talked a big game, as many pirates may have at the time, but he begins our story as only a lieutenant on a far more prominent pirate’s ship. Despite his lowly status, relative to the other infamous pirates of his time, Rackham and his peers were enjoying the absolute heights of the Golden Age of Piracy. Nassau was pure paradise – a centrally located hideout that made it easy for Vane’s accomplished crew to escape out to sea, rob a few ships, then return to their base.

The island itself was heavily fortified, thanks to both natural features and manmade defenses, making it nearly impossible for individual pirate hunters or navy ships to chase down pirates that went to ground there. Once on the island, a thriving pirate community offered all the food, rum, and companionship a pirate could ever ask for. It was a never-ending party, thrown by pirates and enjoyed by pirates. There were no laws, no rules, and opportunities for plunder all around. What could possibly go wrong?

**Between a Rack and a Hard Place**

For the first 15 years of the 18th century, nearly all of Europe was enraptured in the War of the Spanish Succession. Most of the great powers of Western and Central Europe had some sort of claim to the Spanish throne after the death of Charles II in 1700, and the continent spent a decade and a half sorting out the ensuing conflicts. By the time it was over, pirates had complete command of the Caribbean and were engaging in all sorts of shameless pirate behavior with impunity.

When King George the First realized something had to be done to end the piracy, he issued the Proclamation for Suppressing of Pirates on September 5, 1717. All pirates had one year to turn themselves in to a colonial governor and receive complete clemency for all past actions. No tricks. No traps. Pirates could end their pirating and take up a normal life with a normal trade. For an age often marked by near-absolute monarchical power, it was a pretty sweet deal for a bunch of commoners.

The “King’s Pardon,” as it would come to be known in Nassau, deeply divided the Pirate Republic. Some felt that the English Crown prioritizing the end of piracy surely meant that the party was over. A few may have even wanted to take those democratic pirate principles and try to build a real country. But the most vocal group were the “pure” pirates, who declared they’d never bow to the crown. Rackham and the rest of Vane’s crew were squarely in the latter camp.

So when George sent former privateer Woodes Rogers to clean up Nassau and end the party once and for all, Vane and Rackham felt obliged to welcome the would-be governor with a pirate’s greeting. In July of 1718, Vane arranged for a small group of ships to set anchor off the island and fire at Rogers’ incoming frigate; he also set a ship on fire and sailed it directly at Rogers in the hope of destroying his retinue in a slightly more theatrical way. Rogers ultimately survived the attack, while Rackham and his crew escaped out to sea amid the chaos.

Vane and Rackham spent the next four months terrorizing Nassau, Jamaica, and other nearby islands. While Rogers slowly convinced pirates to accept the King’s Pardon, Quartermaster John Rackham was coordinating more attacks than ever. And so it was that Rackham came to his first real spot of trouble.

In November of 1718 – four months after Vane tried to blow up Rogers’s ship, and two months after the deadline for the King’s Pardon – John Rackham and his friends set their sights on a magnificent new prize. This was a French warship, almost certainly filled to the brim with rum, raw materials, sugar, tobacco, and who knows what else. Rackham and his friends badly wanted to take it for themselves.

Captain Vane gave the order to engage, but he quickly realized the pirates were outgunned, and their ship’s superior speed would not be enough to best the warship. Vane wanted to retreat and live to fight another day – an idea that his crew was appalled by. It was a no-win situation for the veteran captain: he could face immediate death by fighting a hopeless battle against a massive warship, or face a potential mutiny by upsetting his increasingly violent crew. Vane was in command, at least for the moment, so he ordered an unpopular retreat.

But after the pirates had safely escaped the French ship, the crew of 70 were predictably mad at the lack of a score. Ever the democracy, Vane’s pirates took a vote, and the vast majority of them were ready for a change in leadership. Charles Vane and his supporters were given a small schooner they had captured days before, and they were sent away. In his place, the crew elected a new man, one who appeared more capable of delivering the mayhem and piracy they were searching for: Calico Jack Rackham.

**A Memorable Wardrobe; A Forgettable Pirate**

Many pirates that sailed through the Caribbean developed some sort of nickname, and newly minted pirate captain John Rackham was no exception. Rackham had a habit of wearing eye-catching clothing made from colorful Indian calico cloth; thus, Calico Jack was born on the high seas. Unfortunately, it didn’t take long for Rackham to realize he made a much better quartermaster than he did a captain.

It was easy to advocate for bold plans and violent delights as a crew member, but Calico Jack soon found that designing and executing glorious pirate plans was a lot harder than it looked. Like a modern-day politician who regrets the promises he made on the way to his election, Calico Jack suddenly had to provide all the plundering that his peers had demanded from Vane. What’s more, he had to do it while Governor Woodes Rogers had begun executing pirates and cleaning up the region.

Rackham started small, targeting low-risk merchants or undefended coastlines. He found modest success and even executed a crafty plan that made it into the pages of Captain Charles Johnson’s *A General History of Pyrates*. According to Johnson, Calico Jack and crew had parked their sloop off the coast of Cuba, and a few men had gone ashore to resupply the ship with fresh food, rum, and ammunition.

At low tide, as the sun was setting, a Spanish gunship responsible for patrolling the Cuban coastline had sailed into view and spotted the pirates. This was a powerful ship that already had a captured English sloop in tow. The Spanish couldn’t mount a proper attack at low tide, so they decided to wait until morning, then attack the pirates at first light. Calico Jack and his crew spotted the Spanish warship and devised a plan. Rather than try to escape from the port at low tide, Rackham ordered the ship abandoned, as everyone fled to shore.

As the Spanish ship fired on the pirate sloop at daybreak, the pirates snuck aboard the captured English sloop, incapacitated the guards, and sailed away before the frigate could realize what had happened. It was a clever move, and one that likely marked the high point of Rackham’s tenure as a pirate captain.

But Captain Jack had just as many setbacks as he did successes. In December of 1718, for example, he targeted a large merchant ship called the Kingston for repossession but drew up a poor plan that almost got he and his crew killed. Rackham liked the Kingston because it was carrying a hugely valuable cargo, but didn’t wait to seize the ship at a tactically isolated area; instead, the crew jumped aboard within sight of Jamaica’s Port Royal, where they could easily be identified and tracked by the ship’s merchants.

They hired bounty hunters, who caught up with the ship several weeks later, at Isla de los Pinos, off the western end of Cuba. Historians are unsure what happened next – some report that Calico Jack and his crew had all gone to land and passed out, leaving their conquest undefended with the loot still aboard. Other versions suggest that Jack opted to hide in the woods rather than fight the hunters. Either way, Rackham was in no position to do anything about it, and he quickly lost his best capture before he had the chance to make any money off the score.

Calico Jack wasn’t disciplined enough to consistently pull off successful pirate heists, and he wasn’t foolhardy enough to launch blind attacks and let the treasure fall where they may. So a few months after overthrowing his captain and living large at sea, Rackham and his crew decided to give up, return to Nassau, and try to convince Governor Rogers to extend them a pardon, months after the King’s deadline.

Upon landing at Nassau, Rackham and his crew were bound and taken before Rogers, where Calico Jack informed him that deposed captain Charles Vane was the real enemy here. You see, none of them actually wanted to be pirates! But Vane had pressed them into service, forcing them to rob and ransack every village in the West Indies. Once Rackham had led a successful mutiny against Vane, those good-hearted pirates sailed straight back to Nassau, hoping to return to normal lives under the English Crown.

It was, quite accidentally, a brilliant plan. Governor Rogers had never forgiven Vane for the fireship stunt upon his arrival and had continued to hold a grudge against him. So in 1719, Rogers officially pardoned Calico Jack and his crew, and they all settled down to live a clean, decent life, free of piracy.

**An Unexpected Turn**

For all we know, John Rackham genuinely did mean to give up his life on the lam when he returned to Nassau and accepted Woodes Rogers’ pardon. However, Rackham hadn’t accounted for the one variable that can make a man do just about anything. It wasn’t long back on land before our former pirate captain ran into a captivating woman in a Bohemian pub. Anne Bonny was an Irish lass who immediately captured Rackham’s attention. The two had instant chemistry and were quickly smitten with each other.

As Rackham settled back into civilian life, he wanted to take Anne as his wife, to have and to hold, as they lived out their days in the sun and the sand. There was just one problem. Anne was already married. Her husband was also a former pirate named John, who had happily taken the pardon and accepted a new job, working directly for Governor Rogers as an informant on pirate activity. In short, he was helping Rogers bring the remaining pirates to justice.

Rackham and Anne Bonny tried everything they could think of to start a new life together. They pleaded directly to John Bonny, with Anne declaring her love for another man. When he said no, they took their case to Rogers, asking that he consider annulling the marriage. In a proposal that’s both sweet and unconventional, Rackham even suggested “Divorce Via Purchase” as an option, offering to buy Anne from John Bonny. Nothing worked.

With no other options available to them, Calico Jack and his lover Anne Bonny decided a pirate’s life was their last recourse. So in August of 1720, Jack, Anne, and a few other friendly ex-pirates stole a ship from Nassau Harbor and returned to the sea. Anne Bonny may very well be the reason we remember Calico Jack at all. Many sailors at the time believed that having a woman aboard a ship was bad luck – even well-respected pirates wouldn’t allow them on their ships.

Successful female pirates were rare, even during the Golden Age of Piracy, which explains why some sources report that Anne may have hidden her gender from everyone but her lover and co-captain. During Calico Jack’s second tour of pirate duty, some records indicate that it was Anne who was both the brains and the brawn of the operation. Years of living through a bad marriage had given her an edge, which she unleashed by seizing dozens of ships and dealing with any captives who might threaten to undermine the operation.

There are plenty of legends surrounding Anne Bonny, including the time she tricked a French crew into surrendering by standing over a bloodied mannequin with a raised axe. Rackham, by contrast, was mostly enjoying the lifestyle that piracy afforded him. He enjoyed his new life with Anne, unencumbered by the burdens of proper civilization, and would often invite sailors from captured ships to drink with him. Some even stayed on as new crew members.

One such sailor who joined Calico Jack’s entourage was yet another woman in disguise: Mary Read. Anne and Mary became fast friends, each seeing through the other’s disguise. Both were elated to find some female companionship on the open ocean and began confiding in each other. In a bit that might as well be pulled straight from a comedy, Calico Jack began to grow jealous of the “lad” who Anne was suddenly spending so much time with. Eventually, Anne had to clue her man in on Mary’s secret!

And for the rest of their days on the sea, the trio carried out raids and thefts, with no one else realizing that two of the Caribbean’s fiercest remaining pirates were women.

**The End of the Adventure**

Unfortunately for Anne, Mary, and Calico Jack, their adventure at sea wouldn’t last more than a few months. Leaving a relatively calm life to become a pirate would be dangerous for anyone; leaving your pirate-snitch husband, absconding with a former pirate, and aggressively robbing every merchant ship from Mexico to the Florida Keys – well, that’s practically inviting trouble.

It took all of one month for Governor Woodes Rogers to announce a bounty for Calico Jack, Anne Bonny, and their crew, and another month after that before bounty hunters were hot on their trail. The walls were closing around John Rackham, and there would be no clever lie to save him this time around. It was only a matter of time before the pirate hunters caught up to them, which is precisely what happened in the final weeks of 1720.

Hunters led by Captain Jonathan Barnet boarded the ship, meaning to bring everyone aboard back to Jamaica to be tried for piracy. Mary and Anne mounted a fierce defense of the pirates, but eventually, they were outnumbered. Once again, accounts differ here – some say Calico Jack was too intoxicated below deck to offer a proper defense, while other reports say he simply recognized he was beaten and quietly laid down his arms.

Whatever the truth, while the women of the ship were prepared to fight until their last breath, John Rackham offered no resistance. He let himself be captured and imprisoned without much resistance, as his remaining crew watched in horror and disgust. Justice came swiftly for Calico Jack and his crew. Anne Bonny and Mary Read were spared from the gallows, as both were pregnant when captured. But the remaining crew – including Rackham – were sentenced to hang, less than a month later, in Port Royal, Jamaica.

Before he died, Anne allegedly visited her lover Rackham in prison. He was overjoyed to see her one last time; she merely scoffed, telling him that “if you had fought like a man, you need not have hanged like a dog.” He was hanged just a few days later, on November 18, 1720, at age 37.

As was the case with many pirates of their day, Rackham’s corpse was displayed as a warning to other pirates. The Jamaicans chose to hang Calico Jack’s body on a small islet outside of Port Royal – a tiny piece of land known now as Rackham’s Cay. It’s probably fitting that John Rackham’s most lasting impact on the world around him was a monument to his own failure.

Calico Jack was not the brightest pirate to ever steer a ship, nor was he the boldest. In truth, he was an imperfect pirate who accomplished very little and earned his fame primarily by the company he kept. He was outlived by Charles Vane, his former mentor, who eventually found himself marooned on an island in the aftermath of a hurricane. He was also outlived by his partner, Anne Bonny, who likely escaped from her Jamaican prison and lived a full life.

The prison has no record of Bonny’s