Bonnet had a rather unsuccessful pirate career when compared to his counterparts, at one point being captured by Blackbeard and subsequently serving by his side to learn the trade. Afterwards Bonnet would set off on his own with moderate success, however this success would attract the attention of local authorities. On this 27th of September 1718, the pirate Captain Stede Bonnet is captured at the Battle of Cape Fear River. In the waning days of the Golden Age of Piracy, the Imperial might of the British Empire had finally begun to crack down on pirate activity in the Caribbean, hunting down and ending the careers of a great number of infamous pirate captains. Among these included the captains of the Pirate Republic of Nassau, such as Edward “Blackbeard” Teach/Thatch, Henry Avery/ Every, Charles Vane, John “Calico Jack” Rackham, and more. This also included Stede Bonnet, otherwise known as “The Gentleman Pirate” for his affluent life as a Barbadian sugar planter before setting out on a life of Piracy.
At the end of summer 1718, Bonnet had managed himself a small pirate flotilla, in which Bonnet piloted the flagship the “Royal James,” a sloop-of-war that was previously a part of Blackbeard’s fleet. Bonnet also had under his command two more sloops, the “Francis” and “Fortune,” as well as a collection of raiding canoes.