Jack Rackham, The Existential Pirate
Jack Rackham, also known as Calico Jack, became a pirate in order to live a life of freedom which was otherwise unavailable to him. It is possible that he began as an officer in the Royal Navy based in Jamaica during Queen Anne’s war and left service some time after that. He went to Nassau, presumably to join the pirate ranks, where the first reference to him as a pirate is as the quartermaster to Charles Vane aboard the Ranger. Accusing Vane of cowardice for failing to attack a French ship, Rackham deposed Vane soon after and became captain of the Ranger.
Operating out of a base on Isla de Pinos, a small island south of Cuba, Rackham and his crew raided shipping going in and out of Jamaica, but they were discovered by the Spanish coast guard and the Ranger was destroyed. Stealing a small sloop that the Spanish warship had in tow, Rackham escaped the island and sailed to Nassau where he accepted Woodes Rogers pardon. It is likely that he was then part of the privateer crew of Benjamin Hornigold and was one of the five men to survive the shipwreck. He made it back to Nassau, but restless, he returned to piracy shortly afterwards by stealing a sloop called the William and taking Anne Bonny and Mary Read along as part of his crew. This last round of piracy only lasted a few months, however. The William was captured and Rackham was hanged.
Unlike other pirates who were using piracy as a means to an end, Rackham can be viewed as having an existential perspective. To him piracy was all about the life itself and living in the moment. He never achieved great wealth, which was probably not important to him, but truly lived, and died, on his own terms.