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.
Jennings and the Spanish wrecks
Jennings’ move towards illegality began with his attempt to salvage gold from the sunken Spanish wrecks in 1715, which had gone down in a storm off the coast of Florida. The news of the catastrophe reached Jamaica in November of that year, setting a wave of piracy in motion. The salvaging of treasure from the wrecks by Jennings and other seaman was considered an act of theft by the Spanish Crown, especially considering that Britain and Spain were now at peace. Jennings had obtained an 80-ton sloop from Archibald Hamilton, the governor of Jamaica, which was called Barsheba. Hamilton also gave him a commission to hunt pirates. In December of 1715, Henry Jennings and Charles Vane captured a Spanish mail ship and obtained the exact position of the main Spanish salvage camp. When he arrived there, Jennings discovered that much of the treasure had already been salvaged and returned to Havana. However, he found a lightly guarded camp at Palma de Ayz and attacked it with about 300 men from three vessels. This proved easier than taking the treasure out of the wrecks themselves. The Spanish soldiers guarding the camp fled, leaving behind about £87,500 in gold and silver. Jennings later arrived in Nassau with the treasure. It is said that while he was there he seized a sloop from Hornigold, who was unable to do much against Jennings’ 200 or more armed men. This creating a lasting animosity between the two pirate captains. After some revelry, Jennings sailed for Jamaica together with Captain John Wills of the Eagle, capturing a small Spanish merchant ship on the way. The Spanish captain was released and reported the act of piracy to the authorities in Cuba. Jennings enjoyed the protection of Hamilton, whom he probably bribed from his ill-earned profits. Hamilton tried to protect Jennings when the Spanish complained to the British government, at least until the pressure grew too great. Hamilton himself was accused of financing the mission to plunder the Spanish wrecks, but denied involvement. Jennings only option was to leave Jamaica after selling off most of his booty.
Jennings the pirate
After leaving Jamaica, Jennings plundered a Jamaican vessel, which promptly returned to the island and reported the incident. Furthermore, because of his plundering of the wreck site some Spanish ships were sent out to hunt him down, but instead they burnt some English vessels while their crews were ashore. Jennings later discovered the marooned sailors of these vessels and integrated them into his own fleet. He then attacked the Spanish wreck site again in January 1716, the leader of the Spanish salvagers offering the pirates 25,000 pieces of eight to leave the site alone, which the raiders readily accepted, also taking some personal possessions and a few cannons from the Spanish. After that, they returned to Jamaica, where Jennings received another commission from Hamilton. He planned to sail to the Spanish wreck site again, sailing out of Jamaica on the Barsheba with Charles Vane on his crew and accompanied by three other sloops: the Mary commanded by Leigh Ashworth; the Cocoa Nut commanded by Samuel Liddell; the Discovery commanded by James Carnegie.
Jennings encounters Black Sam Bellamy
On their way to the Spanish wrecks, the small fleet was near Cuba when it encountered Sam Bellamy and Paulsgrave Williams, who at the time only possessed small periaguas. Bellamy and his men were attempting to capture a vessel, but were frightened off by Jennings, who was flying a British flag. Captain Young, who commanded the vessel being attacked by Bellamy, believed Jennings had come to his rescue, but discovered to his dismay that that the intents of his rescuers were less than honourable. A little later, the pirates saw an armed French merchant ship called the St. Marie at anchor. Jennings first warily checked the ship out and decided it was worth taking the risk to seize it. He planned to attack after nightfall, but before he could do so Bellamy and Williams returned. The pirates agreed to join forces for the attack, capturing the French ship and another vessel that came to trade, unaware that the St. Marie had been captured. Jennings is reported to have tortured members of the crew to find out the whereabouts of the treasure his victims had hidden on shore.
Bellamy’s betrayal
In the meantime, a small boat of men who arrived in the bay to trade with St. Marie were taken prisoner and forced to reveal the whereabouts of their own vessel – the Marianne. Jennings hurried off with Barsheba and Mary to chase it down, but found that Hornigold had beaten him to it. Jennings pursued Hornigold, leaving their slower prize St. Marie behind. Hornigold escaped, so Jennings returned to his prize only to discover that Bellamy and Williams had stolen the treasure stashed aboard it, amounting to about 28,500 pieces of eight. Jennings was unable to catch the culprits, who escaped and later joined up with Hornigold, so he returned to Nassau after, in a fit of rage, burning Captain Young’s sloop and killing some of Bellamy’s men who had remained behind.
Return to Nassau
On 22nd April 1716, Jennings returned to Nassau with the captured St. Marie, where he had some trouble with his crew, who attempted to forcefully take their share of the booty. With some difficulty he finally managed to get them under control. After that, Jennings returned to the wreck site once again, intercepting a salvage ship transporting 30,000 pieces of eight. He then sailed to Jamaica, but was told by Hamilton, who was under pressure from the government, that he’d be arrested if he set foot on Jamaican soil. Hamilton himself was arrested in October 1716. Jennings decided to return to Nassau, which he wanted to use as a base for further raids on the Spanish wrecks. He more or less governed the so-called ‘Pirate Republic’ together with Hornigold, despite the animosities towards each other, calling themselves the Flying Gang.
Jennings’ fate
Jennings was one of the first pirates of Nassau to take the King’s pardon, surrendering himself in Bermuda. After serving as a privateer in the War of the Quadruple Alliance, he he is said to have retired to Bermuda to live the rest of his life “as a wealthy, respected member of society”. Little is known of what happened to him after that. There is a claim that he was later captured and imprisoned by the Spanish or French, possibly while operating as a privateer during the War of Jenkins’ Ear (1739-48) or the War of Austrian Succession (1740-48). Jennings is one of the few pirates in the early 18th century who is though to have enjoyed a wealthy retirement. He remains an unusual example of a pirate, having been a wealthy land owner who had no need to become a sea rover. Perhaps he desired adventure and excitement.