The Real Hackstory of the World’s Worst Midlife Crisis

Have you ever seen the movie Trainspotting? It’s mostly about Scottish heroin addicts and Iggy Pop, but it’s also about the choice people—and maybe men, more often—sometimes make to be self-destructive for no rational reason.

And, while this is the story of Stede Bonnet, who was an English pirate (briefly) in the 1700s, I think the opening monologue for that movie applies here pretty well: “Choose a job. Choose a career. Choose a family. Choose a f*cking big television”—OK, maybe not that last bit.

“But why,” the narrator goes on, “would I want to do that? I chose not to choose life. I chose something else. And the reasons? There are no reasons. Who needs reasons when you’ve got [piracy]?”

This is what I imagine Stede Bonnet was thinking when, in 1717, he quit his life as a wealthy plantation owner on Barbados, quit his marriage, and quit his children to pursue a short, unrestrained, violent life of piracy.¹

What’s Your Deal, Stede?

First of all, I need to get something out of the way: his name is indeed Stede Bonnet. Stede isn’t a typo. I’m not consistently botching “Steve.” Maybe his parents botched “Steve.” At any rate, I’m just going to call him Stede because, as you’ll see, he deserved no better.

Details of Stede’s early life on Barbados are hazy and, quite possibly, boring. He was born in 1688 and purportedly came from a “good English family,” had a solid education, and was “generally esteemed a Man of Letters.” I’m guessing that meant he knew all 26 of the letters and could generally string them together to form sentences. By this definition, I also consider myself a man of letters, though I haven’t experienced any esteem for it. I guess the esteem bar was lower back then.²

His old man died early on, leaving Stede with a 400-acre estate. Little Stede grew up and spent some time serving as a major in the local militia. He was a married man with kids, was wealthy, and could have kept on living in paradise, probably without expending too much effort.^{3 4}

Buuut, in 1717, at the zenith of the “Golden Age of Piracy” (which was only, like, 1715-1720), Stede shirked the hell out of all his responsibilities, bought a sloop (a relatively simple single-mast ship), hired a crew, and set sail under a jolly roger. He christened his new vessel the Revenge. Why Revenge? Since Stede was a privileged man with no apparent enemies, I assume it’s because Stede thought it sounded cooler than, say, Stede’s Inheritance, which wouldn’t have earned him any street cred. After all, no pirate worth his salt would pay for a ship—they stole them from guys like Stede.⁵⁶

But … Why?

Beyond the general midlife crisis assumption, we don’t really know.

Some sources claim he blamed his decision on his wife, which does sound like something Stede would do. There were also rumors that he’d had a mental breakdown, but who hasn’t, right?⁷

There were some warning signs: Sometime shortly before he became a pirate, Stede had borrowed £1,700 (think: $400 grand), so he may have been having financial problems. Stede had lost his first child at some point, and that kind of thing puts a lot of stress on families.

Maybe Stede didn’t know how to handle these things because his father had died when Stede was young, leaving him without a role model, and thus ever questioning the nature of his own masculinity.

Or maybe Stede was just a dick—we really don’t know. If you ask me, though, I think it comes down to this: Stede was only around 29 years old when he became a pirate. He was young, rich, and sheltered. He had spent his life on an island and, after 10 years of being a family man, was overcome by wanderlust. And he was angry: that he’d lost his father as a kid, that his first child had died, and that he was now stuck in his hometown with a family he didn’t seem to want. So, he made a change.

Bonnet Breaks Bad

Stede brought with him over 70 crewmen who probably thought he was a real dandy—but he paid them out of pocket, so they were literally on board with Stede’s ambitions for mayhem and maritime crime.

Mind you, Stede’s only experience with seamanship was that he’d ridden on boats before. But his crew were experienced enough, so the Revenge actually did all right, for a time.⁸ They sailed north and harried merchant vessels around the coasts of Virginia and New England, stealing goods and reportedly burning all captured ships that hailed from Stede’s home island of Barbados—probably to prevent news of his misdeeds from reaching home.⁹

Stede must have gotten a bit cocky after his early pirating success because he ordered the Revenge to attack a full-on Spanish man-of-war. Sloops aren’t good at fighting big f*cking war ships, so half of Stede’s crew died and he was badly injured.¹⁰

Nice going, Stede.

Never Meet Your Heroes

Following Stede’s success, and also that little speed bump where half of his crew died of overexposure to Spanish man-of-war, Stede met a for-real pirate captain. And not just any for-real pirate captain, but the for-real pirate captain.

Edward “Blackbeard” Teach was hanging out in Honduras when Stede showed up for a loot-spending pirate bender. Stede was floored (or decked, if you prefer to keep things nautical) to meet Blackbeard. And Blackbeard was probably pretty excited to meet a rube with money to burn.

So, they agreed to team up. For Blackbeard, “teamwork” meant seizing full command of their combined fleet once at sea. Since Stede was still nursing his wounds from the fight with the man-of-war, Blackbeard made Stede a “guest” on his own ship, the Queen Anne’s Revenge. There, Stede could kick it with Blackbeard and just relax, while Blackbeard’s first mate took over the woeful duty of actually captaining the Revenge. After all, Stede was still nursing his wounds, and even his own crew knew that Stede was a sh*tty pirate captain. Of course, even Stede realized he was a glorified prisoner—or cabin boy, at best—and his bruised ego led him to plot his revenge.¹¹

Stede wouldn’t get his chance, though. After the two had docked their (read: Blackbeard’s) fleet in North Carolina, Stede was sent ashore to a royal pardon for piracy, and was given permission to become a privateer—a legally sanctioned pirate, of sorts, who would only attack ships belonging to enemies of the crown. When he traveled back to port, he found that Blackbeard had stripped the Revenge, abandoned it, and marooned around 25 of Stede’s crew on a small island.¹²

Can you imagine that? Some guy who you relied on just abandons you out of nowhere, takes all your stuff, and f*cks off to go be a pirate somewhere else, without even thinking about your feelings? Can you imagine someone even doing that, Stede? Pretty sh*tty, right, Stede?

The “Gentleman Pirate”

Some men may have been humbled by this experience. Not Stede. Stede had been out-pirated by the best, and it made him double down. Now was not the time for self-reflection, nor was it the time for honoring his pardon and becoming a privateer. Now was the time for doubling down and cranking the pirate knob up to 11.

On the bright side, Blackbeard had given Stede a good reason for his ship to be named Revenge—though he apparently couldn’t appreciate that, since he renamed his ship the Royal James once he returned to piracy, hoping that the name change might confuse authorities and keep his pardon intact.¹³ Blackbeard was long gone by the time Stede got his ship and his crew back, so he vowed to seek vengeance upon Blackbeard.

By this point, Stede had somehow actually gotten a little better at pirating. Blackbeard had a reputation for burning fuses in his own hair, but it seems like his treachery had also lit a fire under Stede’s ass.¹⁴

Initially, Stede sailed after Blackbeard. Once he learned Blackbeard had left the area, Stede focused his efforts on raiding the Atlantic seaboard, capturing ships and splitting treasure with his crew. He embraced his inner bad boy: he killed prisoners, threatened innocents, and even dumped on his own crew for good measure. Word spread, and he finally had a name for himself: the “Gentleman Pirate.”¹⁵

Unfortunately for Stede, his brief spell of luck would soon run out. He had captured a number of ships, but his own—now the Royal James—had begun to leak. In an attempt to clear the hull of barnacles, the ship was run aground. The crew of one captured vessel were released and promptly dropped a dime on Stede, alerting the authorities to the pirate ship that was now careened by lower Cape Fear.¹⁶

Meanwhile, the governor of South Carolina had commissioned Colonel William Rhett to hunt pirates in the area. Rhett had been searching for another pirate, Charles Vane, when he heard about the nearby pirate ships. Rhett altered his course and sailed to the Royal James and its companion ships.

There, Rhett and Stede’s fleets met for the Battle of Cape Fear River. It was also known as the Battle of the Sandbars, because ships on both sides of the fight kept running aground on—you guessed it—sandbars. Over and over again. First, Rhett’s ship, the Henry, ran aground. Thinking the Henry was a merchant ship, Stede sent some rowboats to capture it. Once they got close enough to realize it was a pirate-hunting ship, they rowed on back to warn Stede.

Of course, the Henry was still stuck aground, so Stede had some time to think before the tide came in and mobilized Rhett’s fleet once again. Stede was cornered in the mouth of the Cape Fear River, and needed to get past Rhett’s ships in order to escape into the Atlantic. He decided not to try a nighttime escape, lest he also risk running aground. Instead, he and his pirates would spend the night preparing to fight their way out the next day.

When day broke, Stede began his assault. When Rhett and Stede’s ships met, they exchanged fire, broke formation, and—yep—ran aground on sandbars. They spent the next six hours or so exchanging fire, with Rhett’s Henry getting the worst of it. Stede was feeling pretty alpha, I guess, because he spent the fight patrolling his deck with a pistol, threatening to shoot any of his crew who acted a coward. Up till this point, things were going well for Stede: while his crew had suffered nine casualties, Rhett had lost 30 men.

Then the tide came back in. Contrary to popular belief, a rising tide does not lift all ships—at least, not at the same time. Rhett’s ships were downriver, so the tide raised those first while Stede’s remained stranded. Rhett took full advantage, repaired his rigging and got the Henry into position to fire directly onto the deck of the Royal James.

Stede lost all his sh*t and threatened to blow up his ship, himself, and everyone on board rather than be captured. His crew, however, disagreed, and moved to surrender in spite of their raging captain. Apparently, they were more afraid of taking a full broadside of cannon shot from the Henry than they were afraid of Stede and his little pistol.

Stede’s crew persuaded him to chill the f*ck out and not set fire to the powder magazine on the Royal James, killing everybody. Once things cooled off, Stede’s ship was boarded, and all the pirates got busted.¹⁷

Just like that, Stede’s pirating career ended with more of a whimper than a bang.¹⁸

After a Couple of Years of Bailing on Stuff, Stede Bonnet Finally Hangs Around

Finding himself in custody, Stede became less interested in piracy and blowing himself up, and more interested in being a gentleman again—particularly a gentleman who might be afforded some leniency, perhaps? Oh, and he tried to blame all that unfortunate piracy business on Blackbeard.

While his trial outlasted the lives of his captured crew (who were hanged), his former status only appears to have bought him the extra bit of time necessary for the kind of due process that befitted a more “important” person. For his crimes, Stede Bonnet was convicted of piracy and hanged on December 10, 1718.

The records of Stede Bonnet’s trial for piracy are, to this day, some of the most valuable historical accounts of the lives of both Bonnet and Blackbeard, so I suppose we can consider that his legacy. I wouldn’t give him too much credit for it, though.

As for Stede, well … we may never know why he chose piracy. I do believe the allure of the lifestyle had much to do with it, in spite of—or even because of—the fact that pirates were known for having short and violent lives. Stede certainly got that.

And, as a little bonus, Stede actually outlived Blackbeard, who died in a bloody battle with the British navy just a month prior to Stede’s hanging.¹⁹

So, Revenge after all?

1. Actorama. (Accessed March 16, 2018). https://www.actorama.com/ms/683/John-Hodge-from-the-book-by-Irvine-Welsh/Trainspotting
2. Rankin, Hugh F. (Accessed March 16, 2018). Bonnet, Stede. Retrieved from https://www.ncpedia.org/biography/bonnet-stede
3. Rankin, Hugh F. (Accessed March 16, 2018). Bonnet, Stede. Retrieved from https://www.ncpedia.org/biography/bonnet-stede
4. Blazeski, Goran. (2016, November 22). Stede Bonnet: a pirate and a gentleman. Retrieved from https://www.thevintagenews.com/2016/11/22/stede-bonnet-a-pirate-and-a-gentleman/
5. Rankin, Hugh F. (Accessed March 16, 2018). Bonnet, Stede. Retrieved from https://www.ncpedia.org/biography/bonnet-stede
6. Crawford, Amy. (2007, July 31). The Gentleman Pirate: How Stede Bonnet went from wealthy landowner to villain on the sea. Retrieved from https://www.smithsonianmag.com/history/the-gentleman-pirate-159418520/
7. Blazeski, Goran. (2016, November 22). Stede Bonnet: a pirate and a gentleman. Retrieved from https://www.thevintagenews.com/2016/11/22/stede-bonnet-a-pirate-and-a-gentleman/
8. Crawford, Amy. (2007, July 31). The Gentleman Pirate: How Stede Bonnet went from wealthy landowner to villain on the sea. Retrieved from https://www.smithsonianmag.com/history/the-gentleman-pirate-159418520/
9. Rankin, Hugh F. (Accessed March 16, 2018). Bonnet, Stede. Retrieved from https://www.ncpedia.org/biography/bonnet-stede
10. Blazeski, Goran. (2016, November 22). Stede Bonnet: a pirate and a gentleman. Retrieved from https://www.thevintagenews.com/2016/11/22/stede-bonnet-a-pirate-and-a-gentleman/
11. Crawford, Amy. (2007, July 31). The Gentleman Pirate: How Stede Bonnet went from wealthy landowner to villain on the sea. Retrieved from https://www.smithsonianmag.com/history/the-gentleman-pirate-159418520/
12. Crawford, Amy. (2007, July 31). The Gentleman Pirate: How Stede Bonnet went from wealthy landowner to villain on the sea. Retrieved from https://www.smithsonianmag.com/history/the-gentleman-pirate-159418520/
13. Rankin, Hugh F. (Accessed March 16, 2018). Bonnet, Stede. Retrieved from https://www.ncpedia.org/biography/bonnet-stede
14. Minster, Christopher. (2018, February 26). Little Known Facts About Blackbeard the Pirate. Retrieved from https://www.thoughtco.com/facts-about-blackbeard-the-pirate-2136236
15. North Carolina History Project. (Accessed March 20, 2018). Stede Bonnet (1688-1718). Retrieved from http://northcarolinahistory.org/encyclopedia/stede-bonnet-1688-1718/
16. Rankin, Hugh F. (Accessed March 16, 2018). Bonnet, Stede. Retrieved from https://www.ncpedia.org/biography/bonnet-stede
17. Golden Age of Piracy. (Accessed March 20, 2018). Battle of Cape Fear River. Retrieved from http://www.goldenageofpiracy.org/infamous-pirates/battle-of-cape-fear-river.php
18. Crawford, Amy. (2007, July 31). The Gentleman Pirate: How Stede Bonnet went from wealthy landowner to villain on the sea. Retrieved from https://www.smithsonianmag.com/history/the-gentleman-pirate-159418520/
19. Crawford, Amy. (2007, July 31). The Gentleman Pirate: How Stede Bonnet went from wealthy landowner to villain on the sea. Retrieved from https://www.smithsonianmag.com/history/the-gentleman-pirate-159418520/