John Rackham (26 December 1682 – 18 November 1720), commonly known as Calico Jack, was an English pirate captain operating in the Bahamas and in Cuba during the early 18th century (Rackham is often spelled as Rackam or Rackum in historical documentation, and he is also often referred to as Jack Rackham). His nickname derived from the calico clothing he wore, while Jack is a nickname for "John."
Active towards the end (1718–20) of the "golden age of piracy" (1650–1730) Rackham is most remembered for two things: the design of his Jolly Roger flag, a skull with crossed swords, which contributed to the popularization of the design; and for having two female crew members, Mary Read and Rackham's lover Anne Bonny.
After deposing Charles Vane from his captaincy, Rackham cruised the Leeward Islands, Jamaica Channel, and Windward Passage. He accepted a pardon some time in 1719 and moved to New Providence, where he met Anne Bonny, who at the time was married to James Bonny. When Rackham returned to piracy in 1720 by stealing a British sloop, Bonny joined him. Their new crew included Mary Read. After a short run he was captured by pirate hunter Jonathan Barnet in 1720, before being hanged in November of the same year in Port Royal, Jamaica.
Little is known of Rackham's upbringing or early life, except for the fact that he was English and born around the year 1682. The first record of him is as quartermaster on Charles Vane's sloop Ranger in 1718, operating out of New Providence island in the Bahamas, which was at that time a notorious base for pirates known as the 'Pirates' republic'. After robbing several ships outside New York, Vane and his crew encountered a large French man-of-war. The ship, which was at least twice as large as Vane's sloop, went after them. Vane, claiming caution as his reason, commanded a retreat from battle. Jack Rackham quickly spoke up and contested the decision, suggesting they fight the man-o-war, because it would have plenty of riches. In addition, he argued, if they captured the ship, it would place a much larger ship at their disposal. Of the approximately ninety men on the ship, only fifteen supported Vane in his decision. Despite the overwhelming support for Rackham's cry to fight, Vane declared that the captain's decision is considered final and they fled the man-o-war.
On November 24, 1718 Rackham called a vote in which the men branded Vane a coward and removed him from the captaincy, making Calico Jack the next captain. Rackham gave Vane, and fifteen supporters, the other sloop in the fleet, along with a decent supply of ammunition and goods.
Once gaining the captaincy Rackham made a career of plundering small vessels close to shore. He and his crew captured the Kingston, a small Jamaican vessel, and made it their flagship. They made several conquests in the West Indies, taking a couple of large ships off of Bermuda.
In 1719, Rackham sailed into Nassau in the Bahamas to take advantage of a general amnesty for pirates to obtain a royal pardon and commission from Governor Woodes Rogers. Rogers had been sent to the Bahamas to address the problem of pirates in the Caribbean who had started to attack and steal from British ships.
In December, he captured the merchant ship Kingston. The Kingston had a rich cargo, and promised to be a big score for Rackham and his crew. Unfortunately for him, the Kingston had been taken within sight of Port Royal, where outraged merchants outfitted bounty hunters to go after him. They caught up with him in February 1719, while his ship and the Kingston were anchored at Isla de los Pinos off of Cuba. Rackham and most of his men were on shore at the time, and while they escaped capture by hiding in the woods, their ship - and their rich trophy - was taken away.
In his 1722 classic A General History of the Robberies and Murders of the most notorious Pyrates, Captain Charles Johnson tells the exciting story of how Rackham stole a sloop. Rackham and his men were at a town in Cuba, refitting their small sloop, when a Spanish warship charged with patrolling the Cuban coast entered the harbour, along with a small English sloop they had captured. The Spanish warship saw the pirates but could not get at them at low tide, so they parked in the harbour entrance to wait for morning. That night, Rackham and his men rowed over to the captured English sloop and overpowered the Spanish guards there. As dawn broke, the warship began blasting Rackham's old ship, now empty, as Rackham and his men silently sailed past in their new prize.
Rackham and his men made their way back to Nassau, where they appeared before Governor Rogers and asked to accept the royal pardon, claiming that Vane had forced them to become pirates. Rogers, who hated Vane, believed them and allowed them to accept the pardon and stay. Their time as honest men would not last long.
While in port, Rackham began an affair with Anne Bonny, wife of sailor James Bonny, who was employed by Governor Rogers. After finding out about the relationship, James Bonny brought Anne to Governor Rogers, who ordered her whipped on charges of adultery. Rackham offered to buy Anne in a "divorce by purchase," but she refused to be sold like an animal. The pair (with a new crew) escaped to sea together, voiding Rackham's pardon, by stealing a sloop belonging to John Ham. They sailed the Caribbean for two months, taking over other pirate ships. Often Rackham would invite the crew of ships he attacked to join his own. Anne became pregnant and went to Cuba to have her and Jack's child.
In September 1720, the Bahamas' Governor Woodes Rogers had issued a proclamation declaring Rackham and his crew as pirates—although it was not published until October of 1720. After publication of the warrant, pirate hunter Jonathan Barnet started in pursuit of Rackham, who was by then cruising near Jamaica, capturing numerous small fishing vessels and terrorizing fishermen along the northern Jamaican coastline.
Rackham had come across a small vessel crewed by eleven English pirates, with whom he got into drinking while they were on Rackham's ship, at anchor (and intoxicated) at Bry Harbour Bay in Jamaica, October 1720. His ship was attacked by Barnet's sloop and was captured after a fight presumably led by Mary Read and Anne Bonny. Rackham and his crew were brought to Spanish Town, Jamaica, in November 1720, where they were tried and convicted of piracy, and sentenced to be hanged.
Rackham was executed in Port Royal on November 18, 1720, his body then gibbeted on display on a very small islet at a main entrance to Port Royal now known as Rackham's Cay.
Anne Bonny and Mary Read both claimed to be pregnant at their trials, ten days after Rackham's execution, and so were given a temporary stay until the claim was proven. Read died in April 1721, most likely of fever related to childbirth. There is no historical record of Bonny's release or of her execution.
The day after Rackham's trial, two of his crew members, John "Old Dad the Cooper or Fenis" Fenwick and Thomas Bourn (alias Brown), were separately tried and convicted for mutinies committed in mid-June 1720 off Hispaniola.
All of the eight men (George Fetherston, Richard Corner, John Davies, John Howell, Noah Harwood, James Dobbins, Patrick Carty and Thomas Earl) who'd been drinking with Rackham's crew and were captured with Rackham's crew were tried and convicted in January 1721, then hanged in February 1721.