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Henry Jennings was no desperate outcast. He came from a prominent Bermuda family with estates in Flats Village and ties to former colonial governors, held property in Jamaica, and made his early career as a licensed privateer in the War of the Spanish Succession with his armed sloop, the Barsheba. When the Treaty of Utrecht ended the war around 1713 and 1714, the licenses dried up. Then, in July 1715, a hurricane wrecked 11 Spanish treasure ships near Cape Canaveral. Armed with a commission from Jamaica’s governor, Lord Archibald Hamilton, to hunt pirates only, Jennings instead landed 150 to 300 men in Florida in early 1716, drove off 60 Spanish soldiers at their salvage camp, and carried off a fortune estimated at around 120,000 pieces of eight.

A Spanish captain he had robbed and released trailed him all the way to Port Royal, and the viceroy in Havana threatened to execute English citizens unless the pirates were hanged. Hamilton quietly pushed Jennings out of Jamaica. Jennings turned on English ships, lost a prize to Samuel Bellamy, killed prisoners in a rage, and settled in the ruined town of Nassau, where he led a pirate population that grew past a thousand alongside his rival Benjamin Hornigold in the Flying Gang. When the Crown offered a general amnesty in September 1717, delivered by Woodes Rogers, Jennings sailed to Bermuda in early 1718 and accepted the pardon.

• He tortured the location of the Spanish salvage camp out of the captain of a captured Spanish mail ship.
• He took a 25,000 piece of eight bribe from Spanish salvagers to leave them alone, then robbed them of their possessions and cannons anyway.
• When his fleet attacked the French ship St. Marie, only one captain, Liddell, voted against it, and 23 of Liddell’s own crew joined the raid.
• Bellamy seized the St. Marie at gunpoint and sailed off with 28,500 pieces of eight while Jennings was chasing Hornigold.
• In late 1716 he captured the ship carrying the disgraced Hamilton to England and let it go after taking only 20 gallons of rum.