How would you fare if you decided to leave your job, family, and home behind to sail the seven seas underneath the skull and crossbones?

Well, if you’re ever tempted to do so, local pirate tour guide and author Christopher Byrd Downey has a cautionary tale for you about Stede Bonnet. Bonnet was a wealthy Barbados plantation owner with 400 acres of sugarcane, 200 slaves, and a wife and children. He had neither maritime nor criminal experience, two things one would think were indispensable for someone turning to a life as a shipboard outlaw. Yet none of that stopped Bonnet from deciding, in what Downey compares to a modern mid-life crisis, to become a pirate. And his success rate, for the most part, was what you might expect from someone completely unsuited to his chosen profession. The story of “gentleman piracy” ends, most tragically, with a group hanging in Charleston’s Battery Park.

Stede Bonnet: Charleston’s Gentleman Pirate is filled with the kind of details that make historical reading interesting and memorable. Downey has a knack for narrative and an obvious zeal for his subject. He constructed the history of Bonnet from painstaking research, mostly drawing from the transcripts of Bonnet’s trial, which was held in Charleston in 1718. “It’s pretty interesting reading — it’s word for word,” he says, which not only allowed him to reconstruct Bonnet’s life and the events leading up to the trial, but also provided an authentic flavor and feel for the time.

Bonnet’s story is filled with the kind of false starts and comic blunders that belong in a cheesy comedy. He built his own ship and hired a crew, calling himself captain, but was utterly dependent on his men to actually take care of business. There were more serious problems as well: Bonnet once gave orders to attack a large Spanish vessel, resulting in half of his crew getting killed. He and his ship limped into port at Nassau, broken and defeated — and that’s where he met Blackbeard. “Blackbeard took advantage of [Bonnet],” Downey says. “He used him and his ship for the next full year.”

This is where Bonnet’s story takes a definitive turn, for better or worse, depending on your viewpoint. After joining up with Blackbeard, Bonnet was set on the path to capture, conviction, and hanging. But Blackbeard also gave Bonnet his only true taste of piracy as they joined forces to hold Charleston hostage in a successful multi-day siege. Without Blackbeard, we might not even remember Stede Bonnet’s name.

As Downey writes in his introduction, he first read about the infamous pirate as a senior in high school. There wasn’t much written about him then, and what was written treated Bonnet as “a comic footnote to the Golden Age of Piracy.” “He was kind of a joke,” Downey says, yet he felt that this unlikely pirate was worthy of some understanding and compassion.

Early on in the book, Downey shares how his dreams of being a baseball star were shattered in high school. “Surely, just like me that day in the dugout, Stede had his own moment of clarity when he realized that sometimes you just aren’t the person that you necessarily hope and imagine yourself to be,” he says. “Deep in the grips of my own personal pity party, I thought of the antihero pirate and concluded that if I had been a pirate nearly 300 years ago, my story probably would have turned out the same as Stede Bonnet.”

Stay cool. Support City Paper.

City Paper has been bringing the best news, food, arts, music and event coverage to the Holy City since 1997. Support our continued efforts to highlight the best of Charleston with a one-time donation or become a member of the City Paper Club.