Henry Jennings was an 18th century British privateer who then later helped establish the Republic of Pirates as well as the pirate haven at Nassau in the Bahamas. Like every pirate discussed in this piece, little is known of his early life except that he was a recorded privateer during the War of the Spanish Succession between 1701 and 1714 that operated out of Jamaica which was governed by Lord Archibald Hamilton. Evidence suggests he was a wealthy land owner in Jamaica, which leaves questions for his motivations to piracy.
His first act of piracy occurred in 1716 when he commanded three vessels and 150-300 men including Charles Vane to ambush the salvage efforts of the sunken 1715 treasure fleet. After raiding the Spanish salvage camp and forcing the retreat of 60 soldiers, Jennings and Vane took around 350,000 pieces of eight for their trouble. While en route back to Jamaica they captured another Spanish ship for 60,000 more pieces of eight.
Partnering with "Black Sam" Bellamy, the two set out to commit piracy against the French. Eventually Bellamy double crossed Jennings which caused Jennings to murder 20 French and English men and burned an innocent English merchants ship. After these acts, Henry Jennings was classified as a pirate by Lord Hamilton who commissioned him as a privateer originally. Due to this new sanction, Jennings was forced to flee Port Royal in Jamaica and start a new pirate base in the Bahamas on New Providence. After establishing the pirate haven at Nassau along with the Republic of Pirates, Jennings became the unofficial leader and retired from piracy.
Accepting the 1718 Kings Pardon given by Governor Woodes Rogers, Jennings surrendered and retired as a wealthy plantation owner in Bermuda. Jennings is one of the few pirates in the 18th century and in general to enjoy a retirement. His eventual fate is uncertain, some claim he died of old age in Bermuda and others suggest he was captured by the Spanish and died in prison.