‘Our Flag Means Death:’ Who was the real Stede Bonnet?

It’s borderline flabbergasting, just how much of “the Gentleman Pirate” Stede Bonnet’s actual life was copied and pasted into Our Flag Means Death. Sure, the HBO series takes some creative liberties with the details – shockingly, there doesn’t seem to be any evidence of a leopard-and-piano-and-Tim-Heidecker-based fake-out death on record – but the broad strokes are all there, at least interpretively. 

By all available accounts, the real Stede Bonnet was all of us, in that the lead-up to his 30s hit him like a freight train. That’s about as close to a solid explanation as anyone’s ever come up with for why the 29-ish-year-old retired British Army major and sugar plantation owner flipped the proverbial table in 1717, leaving his life behind for the promise of adventure at sea. There are other theories, too: records indicate that he’d lost a child, and that things weren’t perfect at home, but nothing about the man’s relatively privileged history screams “it’s no wonder he blew up his life.” Like in Our Flag Means Death, it seems likely that he got caught up in a fantasy, wanting to be one of the romantic vigilante brigands of folk legend. Luckily for him, the only barriers to entry were abandoning his wife and children, and owning a pretty big boat.

Borrowing a genuinely staggering amount of money – roughly half a million dollars, adjusted for 300 years of inflation – Bonnet purchased a ship, named it Revenge for no apparent reason aside from that it was a pretty popular name for ships around that time, and promptly got down to the business of making his 70-man crew hate him. His method: The subtle art of ineptitude.

If history tells us anything, Our Flag Means Death‘s Stede Bonnet could be headed for murky waters in season 2

Despite having won some fans in his early days thanks to his wild business model of paying his crew at regular intervals instead of dividing loot whenever there was loot to divide, Bonnet was the Michael Scott of piracy. Yes, his crew managed to win some choice prizes in their first few months, targeting trading vessels off the coast of Virginia, but the general consensus among historians is that Bonnet wasn’t responsible for a ton of wins. Credit goes to his crew, who had a real leg up on Bonnet experience-wise, seeing as they’d all sailed before and he really, really hadn’t. The story goes that by the time the Revenge headed to Barbados later in 1717 and was boarded by Blackbeard, Bonnet’s men were kind of stoked to offer him a World’s Best New Captain mug and put the past behind them. 

Blackbeard offered Stede a sort of Big Brothers/Big Sisters piracy mentorship program that ended with the notorious brigand stripping the Revenge for parts and marooning a good chunk of the crew while Bonnet wasn’t looking. Bonnet swore that he’d get his retribution, presumably shaking his fist in the air and cursing the heavens. He seems like he was probably dramatic like that. He reclaimed his ship and manned it with the sailors Blackbeard had abandoned, setting off in search of the man who’d betrayed him. He never caught up with him.

What Bonnet did catch up with, in the latter half of 1718, were the consequences of his own actions. Despite having claimed a royal pardon at this point, Bonnet decided to get back to the business of scallywaggery, this time going by the pseudonym Captain Thomas and renaming his ship The Royal James in sort of a tragic, low-energy preemption of that mechanic in Grand Theft Auto where you paint your car a different color and suddenly you’re not wanted for murder anymore. 

According to Smithsonian Magazine, when Bonnet found himself cornered by military forces, he swore that he would sooner blow himself up than allow himself to be arrested. His crew took a dim view of this leadership approach and surrendered, presumably eliciting a deflated “Come on, guys” from their now-former boss.

Despite surrendering themselves in a relatively neighborly fashion, the majority of Bonnet’s men were hanged for piracy. Bonnet, meanwhile, employed the defense still used by rich people in trouble to this day: Blaming other people, and saying “but I’m rich.” Unlike nowadays, this didn’t work out. It didn’t help that Bonnet chose to forego legal counsel and represent himself in what would be his last act of almost cartoonish unearned self confidence. The Gentleman Pirate was found guilty of two acts of piracy and, after seven reported delays that the governor made out of a sense of pity, was executed by hanging on December 10, 1718, at age 30.

The second season of Our Flag Means Death premieres October 5, 2023. If it sticks with its historical through line, it should be an absolute bummer.