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A pirate looks through a telescope on a ship

The real Captain Jack: The life of infamous pirate Calcio Jack Rackham


John ‘Calico Jack’ Rackham was one of many infamous pirate captains who plundered the treasures of the Caribbean during the ‘Golden Age of Piracy’.

His was a short but colourful career spanning just two years, but in that time, Calico Jack earned his place in history as the flamboyant pirate captain who set sail with the two most famous female pirates of all time.

From quartermaster to captain

Apart from being English, being born around 1680 and having a nickname he earned thanks to his penchant for wearing fine Indian cotton clothing, nothing is known of Jack Rackham before he turned up as a quartermaster on Ranger, the pirate ship of Charles Vane. Vane was cut from a different cloth to Rackham and one of the most feared pirates of the time. He was a violent thug who thought nothing of torturing and beating crew members of the ships he captured. However, even his fearsome reputation wasn’t enough to save his captaincy when he failed to plunder a ship in 1718.

Vane spotted a French Man-o-War off the coast of The Bahamas. With just two small ships - a brigantine and a sloop - under his command, he concluded the risk of defeat and capture was too great and chose not to attack. Rackham was furious and raised his objections, but Vane wouldn’t be swayed. All but a handful of his crew saw Vane’s withdrawal as an act of cowardice and a missed opportunity to get their hands on some loot. They sided with Rackham, who suddenly looked like a much more attractive prospect than their captain.

Pirate ships operated along democratic lines back then, with crews asked to vote on everything from who should lead them to what targets they attacked. Rackham organised a vote, won the captaincy and relieved Vane of his duties. Rackham’s former captain was given the smaller of the pirates’ two ships.

The following year, Vane was in prison after being shipwrecked and captured. He was hanged on 29th March 1721.

Captain Jack

Rackham wasted no time in his new role. He began attacking smaller ships off the coasts of The Bahamas and Jamaica. His biggest prize was the Kingston, a Jamaican merchant ship that Rackham and his crew managed to steal in 1719. Unfortunately, they stole the ship in full view of its owners in Port Royal, who sent bounty hunters after the pirates.

The bounty hunters found the Kingston anchored alongside Rackham’s ship at the Isla de Pinos off the coast of Cuba. The captain and his crew were onshore at the time; when they returned, they found both the Kingston and Rackham’s ship gone.

Rackham captured another ship and sailed it into Cuba for repairs. While the ship was in the dock, a Spanish warship arrived with an English sloop in tow. Recognising Rackham’s ship, the Spanish attempted to capture it, but low tides meant they had to wait in harbour. While the Spanish ship was at anchor, Rackham’s crew rowed to the captured sloop, overcame its crew and sailed it away while the Spanish warship fired on his old ship, unaware that the pirates had abandoned it.

From Cuba, Rackham sailed to the island of New Providence. He had decided to take advantage of a pirate amnesty and a pardon being offered on behalf of King George I by Woodes Rogers, the governor of The Bahamas. Rackham appeared before Rogers and asked for a pardon, telling the governor that he had been forced into becoming a pirate by Charles Vane. Rogers - who was no fan of the brutal Vane - accepted Rackham’s explanation and granted him a pardon.

Jack attempted to settle down and make an honest living in the town of Nassau, but it quickly became apparent that he wasn’t very good at this lifestyle. Once his cash ran out, he went straight back to piracy. This time, however, he set sail with two crew members who defied the gender stereotypes of their time - Mary Read and Anne Bonny.

The governor, the informant, his wife and her lover

Anne Bonny arrived in Nassau between 1714 and 1718 with her husband. James Bonny was a sailor and former pirate who worked as an informant for Woodes Rogers. Anne frequented the taverns where pirates drank. It wasn’t long before she fell for the charms of the amiable Calico Jack and the two were soon madly in love.

Rackham approached James Bonny and offered to pay him money if he would divorce Anne. An enraged Bonny refused and threatened to beat Rackham for sleeping with his wife. There was nothing for it but for the two to run away to sea, with Anne disguised as a male member of Rackham’s crew because females were frowned upon on board pirate ships in the 18th century.

The formidable Miss Read

Born in England in 1685, Mary was brought up as a boy so her mother could keep receiving maintenance payments from the grandmother of her dead son. That son had died while Mary’s mother was pregnant with her, and to avoid destitution, Mary was passed off as her dead brother and the pair lived off the deceit throughout Mary’s childhood.

After leaving home, Read found employment as a male servant before joining the Royal Navy, again disguised as a man. When the ship she was serving on was raided by pirates, Read was more than happy to join them. She later received the king’s pardon as Rackham had done, but was soon bored of life on land and thirsting to be back onboard a pirate ship. She joined Rackham’s crew when he gave up on life in Nassau.

Back on the high seas

Rackham and his crew stole a sloop and set sail, mainly attacking other pirate ships where Mary Read in particular proved a fearsome and courageous fighter. Anne Bonny was soon pregnant with Rackham’s child. He dropped her off in Cuba as a pirate ship was no place for a pregnant woman or a newborn baby.

Woodes Rogers, meanwhile, sent pirate hunter Jonathan Barnett and former pirate Jean Bonadvis in pursuit of Rackham, who was terrorising small fishing vessels off the coast of Jamaica.

As Bonadvis was sailing to the western tip of Jamaica, he heard a ship fire its cannon. Barnett went to investigate the sloop and enquired who commanded it. ‘John Rackham from Cuba,’ Rackham replied, to which Barnett flew his colours and fired on Rackham’s ship before his men stormed it.

Most of the men on board were having a rum party at the time of the attack and were so drunk that they were incapable of fighting. Instead, they hid below decks and left a recently returned Bonny, Read and a handful of the crew to fend off the hunters. It is said that at one stage an incensed Read fired into the cabin at her cowardly crewmates. After a brief scuffle, the pirates surrendered and were put ashore, where they were arrested and sent to Spanish Town in Jamaica.

The death of Calcio Jack and the end of an era

Rackham was taken from Spanish Town to Port Royal, put on trial and sentenced to death. He was hanged on 18th November 1780. His body was placed in a gibbet cage in a small islet at the entrance to Port Royal. To this day it is still known as Rackham’s Cay. His mouldering bones stayed gibbeted for several years - a warning to others of the fate that awaited those who chose a life of piracy.

Both Anne Bonny and Mary Read would have shared Rackham’s fate were it not for the fact that both claimed to be pregnant. As it was against the law to kill an unborn baby, Read and Bonny were put in prison instead. Read contracted a fever and died in gaol. No record of Bonny’s release or death exists.

By the time of the death of Calico Jack Rackham in 1720, the Golden Age of Piracy was coming to an end. New Providence was no longer a safe haven for pirates and neither were the seas of the Caribbean. By 1726, Blackbeard, Captain Kidd, Black Bart Roberts, Stede Bonnet and Calico Jack were all dead.

The hanging of William Fly in 1726 drew a curtain on the lawless reign of the pirates. The Caribbean would now be a place of law, order and free trade kept in line by the mighty Royal Navy. The days of the pirates of the Caribbean were over for good.