The End of Captain “Calico” Jack Rackham

20 October 1720, while lying drunk in small Jamaican harbour with his crew, the pirate Captain “Calico” Jack Rackham was captured by the pirate hunter Jonathan Barnet.
“First among equals was Calico Jack, by reason of being literate and smart and able to navigate and do all things shipshape and Bristol fashion, look'ee, as his admiring associates often agreed. Also he was strong enough to break a penny between his fingers, which helps, and having served a turn in the Navy, he was reckoned dependable. In our day he would have been a paratroop sergeant, or a shop steward, or a moderate Labour M.P. He was a pirate because it offered a profitable field for his talents, and he was saving for his old age.“ (George MacDonald Fraser, “The Pyrates”)

The Golden Age of Piracy's "Defiance", as imagined by B.F. Gribble (1872 - 1962) 

The end of the War of the Spanish Succession, or Queen Anne’s War, as it was called in the Americas, saw a lot of privateers in the employ of the local governors profiting from raiding enemy shipping for more than 10 years suddenly very unemployed. They had the ships and quite experienced men but no money to pay them. Some turned smuggler along the traditionally closed markets of the Spanish Main. Others changed their trade and became slavers. Most decided to carry on as pirates, or at least tried to, and the French, Dutch and English authorities, hardly better than robber barons themselves during the war, were made to toe the line by their governments. Plundering other nations’ shipping was no longer tolerated and the various navies were out to hunt down the self-employed pirates during the next ten years that were later dubbed “The Golden Age of Piracy” for rather Romantic reasons.

Jack Rackham's Jolly Roger

Jack Rackham came into command of his own pirate vessel in 1718, after the crew degraded their former master Charles Vane off New York. Soon dubbed “Calico Jack” for his choice of extravagant clothing, Rackham began to operate out of Cuba, raiding the shipping lanes and coastal lines of the West Indies out of his small vessel “Nassau”. When he captured the “Kingston” in sight of Port Royal, Jamaica, the local English worthies were really after him, he managed to loose the “Kingston” with her cargo while on shore in Cuba and could barely escape with his crew, but could commandeer a Spanish prize from under the guns of a man-of-war, dubbed the vessel “William” and continued his pirate career for a couple of months. Since all pirates flew their own variants of flags, Rackham’s best known legacy probably is his “Jolly Roger”, showing a white skull with two white sabres crossed beneath it on black ground, the model for Hollywood’s ubiquitous pirate flag.

Bonney and Read, Rackham's illustrious menage from “Ann Bonny and Mary Read convicted of Piracy Novr. 28th. 1720 at a Court of Vice Admiralty held at St. Jago de la Vega in a Island of Jamaica.

Another oddity makes the otherwise moderately successful “Calico Jack” stand out from the crowd, since he was in league with two of the few female pirates known by name, Anne Bonny and Mary Read. Jack met Anne, the wife of a Port Royal sailor, in port and eloped with her, she sailed with him and rejoined the “William” after she gave birth to their child in Cuba and made advances towards a member of Rackham’s crew who was no other than cross-dressing Mary Read and jealous Jack decided to keep her aboard under those circumstances. The whole ménage was finally captured by surprise, again, on the beach obviously after a party, brought to Port Royal and the whole rum lot sentenced to death. Anne and Mary “pleaded their bellies”, that is, they claimed being pregnant and thus couldn’t be executed under English law, Mary died of a fever in prison a few weeks later, Anne was set free, eventually, and might even have continued her pirate career under a different identity – “Calico Jack” and the rest of his crew were hanged in Port Royal in February 1721, their bodies swinging from the gibbets for quite a while afterwards.

An engraving showing Calico Jack
 from Captain Charles Johnson’s and Daniel Defoe’s “A General History of the Pyrates”,