In the spring of 1717, Stede Bonnet sailed from Barbados with a brand new ship and fresh crew never to return. He had decided that he was going to try his hand at piracy. The pursuit of thievery on the high seas was not uncommon during this time period. However, how Stede Bonnet would pursue these goals was exceedingly unusual and continues to be a one of a kind feat to this day.

During this time, all of the classical pirates had backgrounds in sailing. They were all men of the sea. Whether they began as privateers who overstepped their mandates, or as disgruntled merchants tired of risking their wares, all of them were sailors. All of them save for Stede Bonnet. Mr. Bonnet had no known history of sailing and had never owned a ship until he purchased the one he intended to use as his pirate vessel. He was a planter by trade and a major on the island of Barbados. His contemporaries knew him as a wealthy and educated man with no criminal past and no knowledge of the sea. Yet, on that fateful day in 1717, he changed all of that forever.

From Planter to Pirate

Most pirates of the time commandeered their ships, repurposed previous ships, or outright stole them from others. Stede Bonnet commissioned his and purchased it with his own money. It was a sloop that he aptly named Revenge. Knowing no sailors and having no maritime connections, he hired an entirely strange crew and promised to pay them a regular salary. While other captains were dividing spoils and promising plunder, Captain Bonnet was offering a steady living wage, which his men agreed to.

By all accounts, his first campaign as a full-time pirate was a successful one. Relying on the experience of his crew, they sailed from the Caribbean to New York. Along the way, they plundered a variety of vessels off the American coast. They hit the major shipping lanes around the Chesapeake Bay and New York City before turning back south. They plundered eight boats in all. Filled with the glow of success and a belly full of stolen goods, Bonnet turned his ships back south towards the Caribbean, where he planned on stopping in Nassau to collaborate with other pirates of the day.

While sailing for Nassau, Stede Bonnet learned the dangers of piracy first hand when the Revenge encountered a Spanish man-o-war. Anti-piracy measures were ramping up across the region in an attempt to bring an end to the Golden Age of Piracy. Ill-equipped to deal with such an encounter, they attempted to flee. Being the smaller, faster ship, they managed to escape the larger ship but not without severe losses. Some accounts say that Bonnet lost half of his men in the fight, and he was gravely wounded.

Despite the setback, the Revenge and her remaining crew managed to limp to the Bahamas, where they put in and were able to restock, repair, and refit for another campaign.

Enter Blackbeard

During September of 1717, Captain Bonnet spends the month recovering from his injuries in Nassau. Here, he comes in contact with many of the rough and tumble men that have colored our contemporary view of pirates. Not being as weathered or gruff as the rest of the men of Nassau, they quickly began calling him the Gentleman Pirate. His education and eloquence stood in stark contrast to the culture of "The Pirate Republic" that had taken hold in the Bahamas.

His successful first campaign and the strange nature in which he rose to renown out of nowhere attracted the attention of a few prominent men in Nassau, including Edward Teach and Benjamin Hornigold. Both were experienced captains with ragged crews and many battles under their belts. Edward Teach is better known as Blackbeard, while Hornigold was one of the most feared pirates at the time.

Seeing a unique opportunity, Teach strikes up a report with the injured Bonnet and convinces him to cede control of the Revenge to him while he recovers. At the time, Teach was pirating under the command of Captain Hornigold and was eager to strike out on his own once more. The two came to an understanding and set sail at the end of September on another piracy venture. It was at this time that Captain Bonnet would launch himself from oddity to legend and becomes a party to some of piracy's greatest tales.

Blackbeard Takes Command

Still recovering from his injuries, it is not certain if Captain Bonnet was compelled to relinquish command of the Revenge or if he was eager to learn under the more experienced Blackbeard. Either way, at the end of September, the Revenge leaves the Bahamas and sails north on another venture.

Under the unwavering hand of Blackbeard, the Revenge continues her successes and plunders a dozen more ships along the Eastern seaboard. They stopped ships as they left their ports and emptied their holds of all of their valuables before sailing on. The results were good loot, such as vaunted Madeira wine, sugar, and flour. Stede Bonnet accompanies Blackbeard throughout this run but is not in direct command of his ship. He was reportedly ill and unfit for command during this time.

After a successful two-month stint sailing up and down the colonial coast, they make their way back to the Caribbean. Captain Bonnet recovers during this time and is ready to regain command of a ship, eager to put forth what he has learned from Blackbeard.

During their trip south, they encounter a more massive ship called the Concorde, which they successfully sack. The 200-ton ship is hardly damaged, and Blackbeard decides to take this ship for himself. He names it the Queen Anne's Revenge, and it would become a storied ship. The name of this infamous vessel was likely influenced by the name of Bonnet's commissioned boat, the Revenge.

Now, December, the two up-and-coming pirates decide to part ways on good terms. Captain Bonnet has recovered enough to regain control of the Revenge, and Blackbeard has divorced himself of his former captain and secured himself a ship worthy of his talents. Blackbeard sets off south towards the Dutch West Indies. Captain Bonnet decides to try his hand at piracy in the Western Caribbean along the Spanish Main.

In less than a year, the former British planter, with no experience in sailing or naval warfare, has sailed with Blackbeard and was an integral part of two successful pirate campaigns that saw nearly two dozen ships plundered and tons of loot secured. The Gentleman Pirate is ready to make a name for himself.

Failure and Misfortune

The successes of 1717 do not follow Captain Bonnet into 1718. His venture into the western Caribbean is a failure, and he does not document any significant captures during the first couple of months on his own. The continued failures come to a head in March with the loss of a 400-ton merchant ship that they were pursuing off the coast of Honduras. The Protestant Cesar escapes the Revenge and the crew, tired of Bonnet's lack of experience pines for the days of Blackbeard's leadership and threatens a mutiny.

Fortunately for Bonnet's crew, and unfortunately for him, they come across Blackbeard shortly after their failures with the Cesar, and the crew abandons Captain Bonnet for Blackbeard once more.

Aware of their past success together and the friendship that the two captains had enjoyed during their brief time together, Blackbeard takes Captain Bonnet aboard the Queen Anne's Revenge as a guest rather than stranding him somewhere. Discouraged by yet another unfortunate turn of events, Bonnet decides that he is going to retire from his brief stint in piracy. But first, he has to find a way to leave the crew of the notorious Blackbeard.

A Witness to History

As a guest of Blackbeard, Stede Bonnet becomes a spectator to pirate history. Under the command of Captain Richards, he watches as the Revenge captures another sloop and convincing her captain to join their ranks. Another pirate born of an honest sailor. Once they agreed, this brought Blackbeard's burgeoning pirate fleet to a total of three capable ships.

Feeling confident in their crafts and crew, Blackbeard decides to launch his most daring venture yet, and the fleet sails for Charles Town, South Carolina.

In late May 1718, Blackbeard and his pirates blockade the port of Charles Town, a prominent British holding, and stop every ship coming and going into the harbor. Despite being a British holding, the city had no real standing naval presence of their own and had no way of defying the fearsome pirate fleet. The town remained at the whim of Blackbeard for over a week, and he used his overwhelming force to demand supplies and valuables from the frightened citizenry.

Captain Bonnet remained on board the Queen Anne's Revenge for the entire ordeal. In 1718, the Golden Age of Piracy was winding down, and it was acts such as the blockade of Charles Town, which eventually swayed the British to crack down even more harshly on the epidemic of piracy in the New World. This blatant siege of a mainland British colony is one of the last straws that break the camel's back and bring down the full fury of the British Navy on the Caribbean in years to come, ending the nearly hundred-year reign of classical piracy in the region.

After their holds are full and Blackbeard is satisfied with the job they have done to the people of South Carolina, they sail for a favorite hideout on Topsail Island off the coast of North Carolina. However, the Queen Anne's Revenge is run aground on shallow hazards with all of her booty.

Still determined to retire from this life, Captain Bonnet uses the tragedy to slip away to the colonial capital of Bath and seek a pardon for his crimes.

King George had issued a decree which allowed a free pardon to all pirates and privateers who surrendered themselves to British authorities by September 5th, 1718. Seeing a change in his fortunes, Captain Bonnet receives his pardon from the Governor of North Carolina and is even allowed to return to his ship, the Revenge, if he can secure it from Blackbeard on Topsail Island.

Return to the Revenge

Once back at Topsail Island, Stede Bonnet learns that Blackbeard has taken all of their supplies and marooned a large portion of his men on the island. The notorious pirate took the Adventure along with all of the loot from Charles Town and sailed away, leaving nothing behind. Stede Bonnet would be forever grieved by these actions of someone who he considered a friend and colleague, but the two would never cross paths again.

With the early success of his piracy feeling very distant, Captain Bonnet decides that he is going to attempt to secure a letter of marque in the Caribbean and try and bring some legitimacy back to his investment. But the Caribbean is extremely distant, and without the much-needed supplies, Stede Bonnet has no way of procuring the necessary vitals needed to make it back to familiar waters down south.

Under the conditions of his pardon, Bonnet is not permitted to return to any life of piracy, or he faces the gallows. This puts him in a predicament. He has no way of getting back to the Caribbean without resorting to theft, but if he does so so blatantly and nearby to Charles Town, he faces an extreme risk of capture and sentencing.

He tries to circumnavigate this issue by renaming his sloop to the Royal James and going under the alias of Captain Thomas. At first, he tried to swindle other ships under the pretense of legal trade subtly, but he quickly went back to his old ways of straight piracy. It was all his crew knew. Many of the men under his command were veterans of Blackbeard's ships and his previous ventures. They were pirates, not merchants, and they did not know how to do anything else.

It was in this last stint of piracy with the Royal James that Captain Bonnet gives up paying his crew a regular wage. Broke and a veteran of many pirate campaigns, Captain Bonnet, cements himself as a genuine pirate by splitting a share among the crew after plundering a pair of ships.

The End of the Gentleman Pirate

Not wanting to brave hurricane season for the long trek back to the Caribbean, Captain Bonnet decides to try and wait the season out at the Cape Fear River. With some fresh supplies under his belt, he put his ships into rest in September 1718.

News that the pirates who had blockaded Charles Town were depleted and not far away, the governor of South Carolina orders Colonel William Rhett to go against the pirates to right the wrongs done during the blockade. With two heavily armed ships given to him, Rhett sails north to the Cape Fear River to bring an end to the piracy that had plagued the Carolinas.

It is here that the brief and illustrious career of Stede Bonnet comes to an end. The ships block the Royal James in the river, and a battle ensues. The heavy fighting leaves many dead lying in the mud and musket smoke, and the pirates are heavily outnumbered.

Captain Bonnet comes into his own here, finally embracing the mantle of pirate that he wanted to bring upon himself at the start of 1717. He threatens to shoot his crew if they do not fight to the death, he threatens to burn Charles Town harbor if he escapes and tries to blow the powder kegs on the Royal James to give them a glorious end. None of these things come to fruition, and the pirates are forced to surrender.

In the end, the Gentleman Pirate, who caught the eyes and ears of rougher men with his wit and knowledge, becomes the dastardly villain that he has been party to the past year. He is captured and sentenced to death.

Awaiting his hanging, the madness that possibly pushed Stede Bonnet to leave his stable life in Barbados rears its head once more. He pleads with the governor to pardon him and offers his limbs in a trade for mercy. He is hanged in Charles Town on December 10th, 1718.

The man who became a pirate through sheer force of will was a partner to one of the most famous pirates in history, survived many battles, plundered dozens of ships, and eventually met his end in Charles Town, the site of an infamous siege. There was never a pirate like Stede Bonnet before. He was an enigma in everything he did and managed to stumble into some of the greatest moments in pirate history.

Where most pirates were ungraceful, he was eloquent. Where most pirates were sailors, he was not. He bought himself a ship to play pirate and, in the end, became one. Through wit, friendship, and perseverance, he transformed himself from a noble planter to a classical pirate and met the same end as most pirates. He was one of the last great pirates of the Golden Era of Piracy. While not as well known as Blackbeard or Captain Kidd, he managed to carve a name for himself in history against all the odds.