As with so many pirates, the facts concerning 'Calico'1 Jack Rackham's early years are largely unknown. We do not really know when or where he was born, and although he was a fairly active pirate on his own, his enduring fame is due more to his association with the two most famous female pirates of all time, Anne Bonny and Mary Reed, than to any exploits of his own.
Rackham's first documented history dates from 1718 when he was serving as a quarter master with the pirate Charles Vane. Calico Jack was by all accounts a popular and loyal crew member and is likely to have been onboard Vane's ship when they captured a brigantine full of slaves. This ship became Vane's flagship and was the scene of Vane's encounter with the infamous pirate Blackbeard in the September of 1718 near to Ocracoke Island. The encounter between the two ships has become the stuff of legend: a week-long party ensued, news of which eventually reached the ears of Alexander Spotswood, the Governor of Virginia. Spotswood assembled a small force of Royal Naval ships and crew which he dispatched to capture the pirates. This force arrived at Ocracoke on 21 November, 1718, but they were too late. Vane and his crew were spotted two days later 1800km to the south in Windward Passage between the islands of Cuba and Hispaniola2.
Captain Jack Rackham
The sighting of a French ship in the Windward Passage by Vane's crew ultimately proved to be the cause of Rackham's elevation to captain. Vane approached the ship, expecting it to be a normal merchant ship, and prepared the attack. The ship turned a broadside on Vane's small brigantine, thus revealing itself to be a full French Man O'War. Vane decided that living to fight again would be a better idea than engaging, and he ordered a retreat. As Vane was the captain in charge during a combat action, the well-disciplined crew obeyed his orders until they were far away and safe. Then the arguments broke out. Most of the crew believed they could have captured the Man O'War, and as one of the world's early democracies they voted Vane out. Rackham was elected the new captain of the William, and Vane and his few loyal crew members were given a small sloop and cast off.
In July of 1718 the new Governor of the Bahamas, Woodes Rogers, had issued a pardon to any pirate who wanted to receive one. He used this tactic to reduce piracy, as he was able to hire many newly-pardoned pirates as privateers set up to hunt their ex-colleagues. In May 1719 Rackham sailed to Nassau town on New Providence, an island in the Bahamas, to accept this pardon and to settle down. While there he met a woman named Anne Bonny who eventually would create Calico Jack's fame. Anne and Jack were attracted to each other and Anne soon fell pregnant, even though she was married to another, not very successful pirate named James Bonny. Rackham took Anne off to Cuba to be cared for by friends while she had her baby; however, the baby was born prematurely and died shortly afterwards. This devastated Bonny, so Rackham returned her to be with her friends. Meanwhile James Bonny was furious about this betrayal by Anne and went to see Governor Rogers to demand that she be punished. Rogers owed Anne a favour, as she had warned him of an earlier attempt on his life, so instead of punishing her then and there he asked James Bonny to accept Rackham's offer to buy Anne from him. This would have solved everything, except Anne was furious; she refused to be bought and sold like an animal. This caused a problem. She couldn't continue to see Rackham, or else she'd be punished (probably publicly flogged) and she refused to be purchased; so instead she created a third option and ran away to sea with Rackham, disguised as a man!
Calico Jack and Anne Bonny spent the next few months hunting fishing vessels and small merchant ships in the Caribbean. During this time Rackham captured a ship aboard which was another woman, namely Mary Read. She also joined Rackham's crew, and the three set about plundering and pillaging in true pirate fashion. On 20 August, 1720 Rackham stole a small vessel from Nassau harbour and sailed to Negril Bay in Jamaica. He was pursued by Captain Jonathon Barret, a privateer who was hunting pirates across the Caribbean. There is some debate about what happened next. Either there was a short battle which Barret quickly won, or he managed to surprise Rackham. What isn't in doubt is that when Barret's crew stepped onto Rackham's vessel, Rackham and his crew surrendered with little resistance. Mary Read and Anne Bonny, though, fought until they were physically restrained. Rackham was sent to St Jago de la Vega in Jamaica, tried and convicted of piracy on 16 November, 1720. Calico Jack and 11 of his crew mates were hung until dead over the course of two days, 19 and 20 November3. Anne Bonny and Mary Read escaped the death penalty by declaring that they were pregnant.
Calico Jack Rackham was never a hugely successful pirate. Most of his robberies were on a fairly small scale, and he'd have probably drifted into obscurity after his death if it weren't for his association with the two women pirates. Yet he must have been disappointed with the last words he had from the love of his life, Anne Bonny. She stated that 'she was sorry to see him there in gaol, but if he had fought like a man, he need not be hanged like a dog'.