Unusual, unlikely, and unprepared best describe Stede Bonnet who was an educated, affluent and respected plantation owner, until he decided to become a pirate.
Major Bonnet, as he was known for his affiliation with the island militia, was a wealthy sugar plantation owner from a respected English family. He lived in Bridgetown, in Barbados, where he mingled with the island's elite. In 1717, in his middle age, he abruptly abandoned his comfortable life for a career as a pirate. It was a career in which he had no experience. His decision scandalized the polite society of Barbados, and Bonnet's acquaintances thought him emotionally disturbed. Others speculated he turned to piracy to escape his nagging wife.
Rather than stealing or capturing a ship, Bonnet bought one, something unheard of for a pirate. The ship had a single gun deck with 10 pieces of artillery, and Bonnet named it "The Revenge." Bonnet recruited his gang from local taverns, organizing a band of about 70 men. Rather than drawing up a contract for the men to sign, as was customary, Bonnet paid his crew a salary from his own pocket. This, too, was unusual for a pirate, but it helped him retain command over the men.
Bonnet kept his ship in the harbor for several days, before leaving one night with no word to his family. Though inexperienced, he was moderately successful, taking ships off the Virginia and Carolina coasts. He merely plundered the first few ships, but after burning one, the Turbes, he burned every one he took. By this time his men had realized his inexperience, and hostility began to brew. While anchored at the Bay of Honduras or possibly while cruising the Carolinas, Bonnet met Edward "Blackbeard" Teach. Teach invited Bonnet onto his ship, the Queen Anne's Revenge, then took Bonnet's ship. Bonnet was essentially a prisoner on Teach's ship, although by some accounts, he contentedly spent his time there reading and walking the decks.
It is known that Bonnet was pardoned, by some reports Teach suggested he request a pardon, others say it was upon hearing that Britain and Spain were at war that he requested the pardon. It is also clear that Teach returned Bonnet's ship to him, but the circumstances of that exchange are unknown. After being pardoned, and armed with a letter of marque to capture Spanish ships, he set sail for St. Thomas in the British Virgin Islands. To disguise himself, he renamed his ship the "Royal James," and took on the name Capt. Thomas. While en route to the islands he was rumored to have gone searching for Blackbeard but didn't find him, and returned to piracy, again faring well. Bonnet was eventually captured by Col. William Rhett, who had been sent after pirates operating near Charleston. Bonnet escaped, but was recaptured, and brought to trial in a Court of Vice-Admiralty in Charleston. Despite a moving letter he reportedly wrote begging the governor for clemency, Bonnet was sentenced to death by hanging, along with 29 of his men. During his sentencing Judge Trot was said to have made a great speech, reporting that Bonnet had killed no less than 18 men sent to capture him, and that was no way for a "man of letters," to behave. Nicknamed "The Gentleman Pirate," his education hurt him in the end. He was hanged for piracy Dec. 10, 1718, and his body was left hanging for four days as a warning to other pirates.