Category: 1700 to 1718

Henry Jennings was an unusual pirate, being a wealthy landowner with estates in both Bermuda and Jamaica. His family were well established on Bermuda, living in Flatts Village in the Hamilton Parish of the island. Little is known of his early life except that he was a privateer during the Spanish War of Succession operating out of Jamaica, where he developed a close relationship with Governor Archibald Hamilton. At times he could be cruel and self-serving. He was also believed to be a supporter of the Jacobite cause. He was later based in Nassau after turning from privateering to piracy, becoming a mentor to Charles Vane and an adversary to Benjamin Hornigold.

Stede Bonnet is sometimes referred to as ‘The Gentleman Pirate’. Historically, he has often been viewed as more of a comical or tragic figure, who wasn’t always taken seriously. This image was probably fuelled by his inexperience in matters of seamanship. He was a descendant of Oliver Cromwell and a distant relative of Woodes Rogers. Born on Barbados in about 1688 and his parents, Edward and Sarah Bonnet, owned an estate of over 400 acres south-east of Bridgetown, which he inherited in 1694. He was well-educated and gained the rank of major in the Barbadian militia, although there is no record he was ever involved in any combat. He was made a justice of the peace a year before he turned to piracy. He married Mary Allamby in November 1709 and had three sons and a daughter with her. It has been speculated that he suffered from depression or some other sort of mental disorder, possibly caused by the death of his eldest son in 1715.…

Often overshadowed by her fellow pirate Ann Bonny, Mary Read is still better-known than many pirates with more successful pirating careers. Read and Bonny stood out because it was unusual at the beginning of the 18th century for a woman to be part of a pirate crew. Pirates, like all seamen, generally frowned upon a woman’s presence aboard a ship. Not so much is really known about Read’s early life, the main source being her trial documents, newspaper articles, and Charles Johnson’s A General History of the Pyrates. According to Johnson, Read’s unnamed mother is said to have been married to a seaman, who went to sea and never returned. Her first child, a son, died, but she then gave birth to Mary out of wedlock. One theory is that Mary’s mother was Ann Cantrell, who is recorded as sending a letter to Adam Baldridge, a smuggler and ex-privateer on Madagascar, laying claim to some money that her husband, a pirate called John Read, who died on Madagascar some time prior to 1698, had entrusted to Baldridge.…

“She was of a fierce and courageous Temper, wherefore, when she lay under Condemnation, several Stories were reported of her, much to her disadvantage, …” Captain Johnson, A General History of the Pyrates, 1724

Ann Bonny, her first name sometimes spelt Anne, was one of the two notorious female pirates who sailed with Jack Rackham. Much has been written, but no so much is really known about her life. It is unclear where she really came from. It is often claimed she was born in Ireland, but there is no evidence of this, although it can be assumed she was born sometime in the late 1690s. No primary source, including her own trial transcript, makes mention of her age or nation of origin. No records of an Ann Bonny being born in the late 17th century have been found in the list of baptisms of Ireland. Bonny is not noted as having been an inhabitant of Nassau before pirates arrived in 1713.…

Rackham’s true first name was John, Jack being a nickname for John, said to have originated from the Middle English variation of John, which was commonly pronounced as ‘Jankin’ or ‘Jackin’, over time being shortened to ‘Jack’. His surname is usually spelt Rackham, although other spellings appeared in sources of in a time before spelling was standardized, such as Rackam, Rackum, Racum, or even Racan. The nickname ‘Calico Jack’ first appeared in the 1728 edition of Charles Johnson’s A General History of the Pyrates. It has been claimed he was born in Bristol, England, in 1682, but there is no surviving evidence of this. He is often considered as having been one of the least successful pirates of the Golden Age, only having captured fourteen vessels over a short period, seven of which were fishing boats, one a canoe, the others small trading vessels, obtaing no more than £1400 in plunder.…