A wealthy plantation owner with zero sailing experience quit his life of comfort to become a pirate — and paid his crew a salary instead of plunder shares.
Stede Bonnet was born around 1688 into a rich family in Bridgetown, Barbados, and inherited over 400 acres of estate land as a teenager. He became a militia major, married, had four children, and lived as one of the wealthiest men in Bridgetown society — nothing about his life pointed toward piracy.
In spring 1717, with no sailing experience at all, Bonnet abruptly bought a sloop, armed it with ten guns, and hired a crew of more than seventy men — paying them fixed wages instead of the customary share of stolen loot, an arrangement no real pirate captain would ever offer. Historians suspect he was fleeing an unhappy marriage rather than chasing riches.
He earned the nickname 'the Gentleman Pirate,' plundering ships along the Virginia and New York coasts through 1717. Sailing toward Nassau, he ran into a Spanish warship, lost half his crew, and was badly wounded in the fight.
At Nassau he fell in with Blackbeard, and the two formed an odd alliance. Too injured and inexperienced to command, Bonnet let Blackbeard take charge of his own ship — who then effectively held him prisoner aboard as a pampered 'guest,' reasoning a gentleman like Bonnet would rather relax than lead.
When Blackbeard's flagship Queen Anne's Revenge ran aground in June 1718, he let Bonnet have his ship back — then secretly stole Bonnet's supplies and scuttled several of the fleet's other vessels before vanishing. Both men had just accepted a royal pardon from the governor of North Carolina.
Rather than go straight, Bonnet renamed his ship the Royal James, adopted the alias 'Captain Thomas,' and went right back to piracy under a fake name — hoping to keep his pardon on paper while breaking it in practice.
In September 1718, while anchored on North Carolina's Cape Fear River repairing his ship, Bonnet was cornered by two government sloops in the Battle of Cape Fear River. His men fought fiercely but were trapped by the tide, and his crew forced him to surrender against his wishes.
Bonnet briefly escaped custody in Charleston but was recaptured days later. He wrote a desperate letter begging to become a 'menial servant' rather than die, but the governor refused. On December 10, 1718, Stede Bonnet — the pirate who started with a fortune and a salary for his crew — was hanged, and his body dumped in a marsh with no marker.