Black Sails: 10 Pirates Who Should Appear In Season 2

10. Henry Jennings

Real or storybook? Real. Who is he? A privateer (government licenced pirate - plundering for patriotism) who turned pirate after the end of the War of Spanish Succession in 1714, Jennings accepted an amnesty on pirate crimes a few years' later and retired into a comfortable life as a plantation owner on Bermuda. He remains one of very few famous pirates to achieve a large treasure haul and live to tell the tale. Most pirates didn't quit while they were ahead. Where would he fit into Black Sails? At the end of Season 1 Captain Flint's ship the Walrus was wrecked by a Spanish warship, beaching his crew conveniently on the same stretch of coast as their prey, real life treasure ship Urca de Lima, after it ran aground in a storm. Meanwhile, Captain Charles Vane returned to New Providence to take control of a new position of power. In reality the actual Vane assisted Jennings in acquiring the real treasure of the real wrecked Urca de Lima after they plundered a Spanish mail ship carrying details and the location of the Urca's salvage operation (obviously the inspiration for the stolen schedule in Black Sails' Season 1). In the show Jennings could therefore appear as a pirate captain sent by the newly empowered Vane to hunt the Urca treasure before Flint can take it, creating a new rival for the show's protagonist. In fact the only real reason not to include Jennings in the Urca de Lima plot is that he is perhaps too much the inspiration for Black Sails' Flint and the characters potentially too similar.