Raising the Black Flag : Pirates in History & Imagination

"Calico" Jack Rackham (1682-1720) 

John "Jack" Rackham was an English pirate who operated in the Bahamas and Cuba. 

Known as Calico Jack due to his colorful clothing. Served as Charles Vane’s quartermaster, before turning on Vane in order to get a pardon from the governor of the Bahamas, Woodes Rogers. He would later sail with both Anne Bonny and Mary Read before being captured in Jamaica and executed in Port Royal.

His first mate designed the Jolly Roger flag, which has since become a ubiquitous symbol of pirates and piracy. He is also portrayed directly and indirectly in a number of works of literature about the golden age of piracy, including serving as the inspiration for Herge’s character “Red Rackham” from the long-running Adventures of Tintin comic series. 

Mary Read (1685-1721) 

Mary Read grew up being passed off as a boy by her mother in order to gain additional financial support from distant family members after the death of her older brother. 

During her teens, she joined the British military as a man before sailing to the West Indies. She originally joined her first pirate crew because her ship was attacked by pirates, but later took a commission to sail as a privateer before joining Jack Rackham’s crew. There was much contemporary debate and speculation about the nature of the relationship between Mary, Anne Bonny, and Jack Rackham, which continues to this day. When the rest of the crew was captured in 1720, she along with Anne Bonny was given a stay of execution due to being pregnant, although it appears that Mary later died in prison.

Along with Anne Bonny, Mary Read is one of the best-known western woman pirates and features in many pop culture adaptations of the Golden Age of Piracy.

Anne Bonny (1697-Unknown) 

Anne Bonny moved to Nassau during the Republic of Pirates period along with her husband, James Bonny, who ultimately became an informant for the governor, Woodes Rogers. She divorced her husband and joined Jack Rackham’s crew, disguising herself as a man. However, her identity was discovered by Rackham and later on by Mary Read, who was also part of the crew. She and Read were both captured along with the rest of Rackham’s crew in 1720, although they were given stays of execution because they were pregnant. Anne later escaped from prison after her child was born and disappears from history.