Henry Jennings was one of the early members of the pirate republic in the Bahamas, and the leader of one of the two major pirate factions there. Apparently motivated by a desire to restore the Stuarts to the British throne, Jennings was one of the more violent and merciless pirates, with far fewer reservations about using deadly force against opponents, captives, and rivals.
Jennings was a wealthy and successful merchant captain, an educated man with an estate on Jamaica. As revealed in The Republic of Pirates, he did not intend to become a pirate but, rather, was involved in the global conspiracy to overthrow George I and put James Stuart on the throne. Under the direction of the pro-stuart Governor of Jamaica, Archibald Hamilton, Jennings armed his 80-ton sloop Bathsheba and at the end of 1715 sailed out to salvage loot from the wrecks of the Spanish treasure fleet. Instead, he launched an all-out assault on the Spanish salvage camp at Palma de Ayz, Florida, stealing £87,000 in gold and silver. He then put in at Nassau, where he offended Hornigold, before returning to Jamaica on January 26, 1716.
Although his raid was illegal — Britain and Spain were at peace — Jennings was unmolested by Jamaica authorities. He set out again in March, sailing to Cuba where, on April 3, he illegally seized a French merchant ship with the help of a motley group of pirates lead by Samuel Bellamy. Bellamy subsequently stole a large portion of the treasure and slipped away to join Hornigold, who happened to be operating in the area. This attack on neutral French shipping triggered a diplomatic storm that ultimately resulted in Jennings being declared a pirate by King George. He moved his operations to Nassau, where he would remain a leading figure for the next two years. Like Hornigold, he did not target English ships.
When word of the King’s pardon reached Nassau in late December 1717, the pirates split into two camps, one wishing to take the amnesty, the other intending to carry on to the bitter end. Jennings was one of those who chose clemency, though curiously he and his close followers chose to surrender in Bermuda, not Jamaica, a decision that fuels speculation that Jennings had family ties there. He re-outfitted Bathsheba there and reportedly cruised the Bahamas hunting Charles Vane and other recalcitrant pirates; he did not return to Nassau. During the War of the Quadruple Alliance he was a successful privateer and, subsequently, he enjoyed a successful merchant career out of Bermuda. In 1745, during the War of the Austrian Succession, he was captured by the Spanish and presumably died in custody.