Stede Bonnet · The Flying Gang

Stede Bonnet is the great oddity of the Golden Age. Nearly every pirate came to the trade from the sea — a merchant sailor thrown out of work, a privateer turned outlaw, a pressed man who joined his captors. Bonnet came to it from a sugar plantation. He was a moderately wealthy and reasonably educated landowner of Barbados, a retired militia major with a wife and children, and he knew almost nothing about ships.

The ship he paid for

Around 1717, for reasons never satisfactorily explained — Charles Johnson attributes it to "a disorder in his mind" brought on by his marriage — Bonnet did what no other pirate is known to have done: he bought a vessel with his own money. He fitted out a ten-gun sloop, named her the Revenge, hired a crew on wages rather than shares, and set off up the American coast to rob shipping. His inexperience showed at once, and his men had little of the loyalty that plunder-shares bought other captains.

Under Blackbeard's thumb

Off the Carolinas, Bonnet fell in with Edward Teach. Recognizing an amateur, Blackbeard invited Bonnet aboard his own flagship as a "guest," installed one of his own officers to command the Revenge, and effectively relieved Bonnet of his ship and his authority. Bonnet spent months as a passenger in another man's fleet. When Blackbeard broke up the company at Beaufort Inlet — grounding the Queen Anne's Revenge and making off with the loot — Bonnet at last recovered his sloop.

Relapse

Bonnet took a royal pardon and a commission to privateer against the Spanish, but soon returned to plain piracy under the alias Captain Thomas, renaming the sloop Royal James. In the late summer of 1718 he lay up in the Cape Fear River to careen and refit — and it was there that a South Carolina expedition ran him to ground.

White Point

Captured, escaped, and recaptured, Bonnet was tried at Charleston before the vice-admiralty judge Nicholas Trott. His pleas for mercy — and reportedly the town's sympathy for a gentleman fallen so far — could not save him. He was hanged at White Point, Charleston, on 10 December 1718.