As far as pirates go, Stede Bonnet was one of the more unusual rogues. An established plantation owner on the island of Barbados, Stede was educated, relatively wealthy, and living a comfortable life among upper-class society when he suddenly, and for no known reason, left his plantation owner's life to become a pirate. Since most pirates of the Golden Age were lower-class, uneducated, poor working men, this set Bonnet apart from the majority of his contemporaries, especially in regard to his ship and crew.
When Bonnet decided to become a pirate he purchased his own ship, rather than stealing or capturing one as most pirates did. His ten-gun sloop was called the Revenge, for reasons Bonnet shared with no one. Going against normal pirate convention, Bonnet did not have his men sign ship's articles, instead paying them with his own money. He found his crew of about seventy men by going into the taverns in Bridgeport, Barbados, and offering out-of-work seamen jobs as pirates. He told his family and friends that he'd purchased the ship and hired a crew in order to trade between local islands. He then departed in the middle of the night, headed not for other islands, but for the Virginia Capes, the New York coastline, and finally the coast of the Carolinas, where he and his crew plundered several ships, captured a few for Bonnet's own use, and burned the remainder.
In the fall of 1717, Bonnet met up with Blackbeard, who took the Revenge for his own fleet and kept the gentleman pirate onboard his ship, the Queen Anne's Revenge. Eventually Blackbeard returned to Ocracoke Island, where he allowed Bonnet to take his own ship and leave. Bonnet subsequently went to the governor of North Carolina and secured a pardon and a letter of marque authorizing him to attack Spanish ships. Whether Bonnet intended to “go straight” as a privateer or not, he became sidetracked off Ocracoke Island where he was hunting for Blackbeard, whom he was still angry with over the taking of his ship and his share of loot. He didn't find Blackbeard, but he did decide to revert to piracy, capturing another nine vessels off the Virginia and Carolina coasts, before heading into the Cape Fear River to careen his ship's hull. This pit stop would prove costly, as Colonel Rhett, who was following the false leads Charles Vane had left for his pursuer, found not Vane but Bonnet and his crew. With their ship run aground the pirates were unable to leave, and after a fight that lasted a few hours they surrendered. Rhett took Bonnet and his crew prisoner and moved them to Charleston, where they were imprisoned awaiting trial. Bonnet escaped, but was recaptured; in November of 1718, he and thirty of his crewmembers were hanged.
The term careening refers to a process where a wooden ship is taken to a shallow area, the masts pulled to the ground, and the ship placed on its side so that it can be repaired and cleaned of seaweed and barnacles that make it awkward to steer. This had to be done every two or three months, and was the most dangerous time for a pirate crew as they were extremely vulnerable to attack.