The Real Gentleman Pirate

The true story behind Our Flag Means Death


The HBO series Our Flag Means Death takes a comical look at a gentleman landowner named Stede Bonnet, who decides to try his hand at piracy. The show portrays Bonnet as a bumbling fop, unsuited for the life of piracy on the high seas. However, his unwavering idealism inspires crew members to put up with his antics.

In reality, Stede Bonnet became one of the most infamous pirates of his day. While it was confirmed that he knew little of pirating when he decided to leave his wife and children for a life of adventure, he proved himself to be a somewhat capable leader. As in the show, the genuine Bonnet partnered with the notorious Edward “Blackbeard” Teach, who helped show Bonnet the ropes of piracy.

A Pirate Life for Me?

In the 18th century, piracy was the trade for the oppressed. Many were formerly enslaved or poor, uneducated people who had few options to make a living. Some had a level of military training and used skills in the Royal Navy to seek fortune and notoriety. It was a way to fight back against the wealthy establishment and live outside society’s expectations.

This makes the fact that Stede Bonnet went into piracy more puzzling. Sources say that Bonnet came from the gentry class in Barbados in the 1680s. He was given a liberal education and retired from the military with the rank of major. In the years that followed, Bonnet bought a sizable estate and settled down for the life of a family man. He and his wife, Mary, had three sons (Edward, Allamby, and Stede) and a daughter named Mary.

Around 1717, Bonnet suffered some sort of mental break and decided he wanted to try his hand at pirating. As in the HBO series, some theorize that Bonnet became bored with married life. Others think he may have experienced financial troubles and turned to piracy to recoup his losses. Still, others believe he may have been a Jacobite, a member of society who still supported the Stuart claim to the British throne and saw King George I as a usurper. Many pirates saw themselves as rebels supporting the “true king,” James III.

In the Spring of 1717, Bonnet purchased a small sloop and named it the Revenge. He developed the moniker of the Gentleman Pirate to pay homage to his aristocratic background. With a crew of 70 men and ten cannons, he left his wife and children behind for a life of piracy. His first target was the coast of the Virginia Colony.

Bonnet was fortunate to have a skilled crew under his command. While he was not an experienced sailor, many of his men were veteran pirates and sailors. The crew raided commercial vessels and had several initial successes. The crew sailed for Honduras and the Republic of Pirates, a known haven for pirates following these early successes. It was here that the crew would spread their wealth and catch the eye of one of the most notorious pirates in history.

Teaming With Blackbeard

Edward Teach was one of the most famous pirates. Born in Bristol, he worked his way from deckhand to the captain of his ship. Teach earned the moniker Blackbeard and was notorious for his ferociousness in battle and ruthless command. With the Queen Anne’s Revenge, he became famous as the captain and drove fear in the hearts of those who encountered him.

In Honduras, Bonnet encountered Blackbeard, and the two struck up a friendship. They agreed to sail together, and Blackbeard quickly realized that Bonnet was an amateur and skilled enough to command his crew. Blackbeard seized Bonnet’s ship and gave command of the Revenge to Bonnet’s first mate with the agreement of Bonnet’s crew.

Blackbeard rationalized that Bonnet did not have the skills to command a pirate crew, so stepping down was in his best interest. Instead, he should relax on board Blackbeard’s flagship while more skilled men did the pirating. Bonnet would spend the time on board Blackbeard’s ship plotting his revenge. While nominally Blackbead’s guest, Bonnet was his prisoner.

At one point, Blackbeard docked off the coast of North Carolina. Following the siege of Charles Town, Blackbeard convinced Bonnet it was wise for him to seek out the governor and seek amnesty for his crimes. It seemed like an easy out for a man that was not cut out for a pirate’s life. Instead, he could serve as a privateer in the war against Spain.

Bonnet plotted revenge on Blackbeard, but the skilled captain had too good of a headstart, and Bonnet contented himself with resuming attacks on merchant’s vessels. Bonnet went ashore, only to return and find Blackbeard had stripped and abandoned the Revenge while also leaving Bonnet’s crew marooned on a nearby island. Bonnet took possession of his ship back and rescued his crew.

While Bonnet was commissioned as a privateer in the war between England and France, Bonnet also bided his time to take his vengeance on Blackbeard.

Like many of his fellow pirates that received pardons, it was not long before Bonnet went back to his old ways. Renaming Captain Thomas and rechristening his ship, the Royal James, he returned to piracy. However, the more experienced Bonnet had changed, not for the better.

A New Ruthlessness

A change came over Bonnet following his time with Blackbeard. His leadership skills appeared to improve. However, he also developed a new mean streak. Bonnet began to abuse his crew, kill prisoners, and threaten civilians. Through these actions, Bonnet developed a fearsome reputation of his own.

His new reputation caught the attention of the governor of South Carolina. In 1718 Colonel William Rhett was commissioned with finding and capturing the Gentleman Pirate. In August of that year, Rhett cornered Bonnet at the mouth of the Cape Fear River. After a fierce battle, Rhett captured Bonnet and most of his crew. Bonnet had declared he would blow himself up with the ship before being caught, but his crew overruled him. The brief career of the Gentleman Pirate Stede Bonnet was over.

Trial and Execution

Bonnet attempted to use his aristocratic background in his defense at his trial. Bonnet appealed to the governor for mercy and tried to blame his crimes on Blackbeard. Through his appeals, Bonnet’s trial stretched on long after the rest of his crew had been hanged. The trial transcript gives us a wealth of knowledge about Bonnet and Blackbeard.

Bonnet was finally convicted and hanged for piracy on December 10, 1718. His career as a pirate lasted less than two years. He may have taken some solace that his old rival had met his end a month before. Blackbeard died in a bloody battle with the Royal Navy on November 22.


Stede Bonnet was not quite like the character portrayed in the HBO series. While he was a gentleman aristocrat who was at first unfit for piracy, the second half of his career showed a ruthless streak that gained him notoriety.

He has popped up in pop culture since the 18th century in literature, television, video games, and film. Stede Bonnet is one of the more interesting characters in the Golden Age of Piracy, and we would likely not know his name had he remained a quiet sugar plantation owner.



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Nick Howard

Nick Howard

I am an educator and a writer. My topics of interest include sports, movies, comics, history, professional wrestling, food, music, and hobbies.