The Real History Behind Our Flag Means Death

It may be a pirate comedy starring writer/producer/actor Taiki Waititi (What We Do in the Shadows, Thor), but Our Flag Means Death is also a history lesson based on the wild, real-life story of aristocrat Stede Bonnet, a “gentleman pirate” whose mid-life crisis led him to abandon his family and sugar plantation in Barbados for the high seas — despite not being suited to a life of violence and thievery on the high seas. In the course of his bumbling adventures he crosses paths with the notorious pirate Blackbeard (Waititi), who agrees to teach him how to become a feared pirate in exchange for lessons in how to fit in with genteel society.

At the heart of Our Flag Means Death lies this complex relationship. In reality, Bonnet and Blackbeard were contemporaries who knew each other well. One was the most deadly and feared pirate ever; the other had no clue how to sail. As Our Flag Means Death unfolds each week, we see that friendship grow and strain under the demands of 18th century piracy. But what’s the truth behind the fictional versions of these two diametrically opposed men? Tread carefully in these waters. I’m going to dive into their history, so this is your spoiler alert. Consider yourself warned, mateys!

Bonnet and Blackbeard

Why did Bonnet turn to piracy?

Stede Bonnet and Blackbeard operated during the height of the pirating era, around 1717-1720. This is the period that all our pirate stereotypes are built on today. Thank you, Robert Louis Stevenson. I imagine the romance of piracy was as strong then as it is today at Disneyland, and just as far from the truth of it. But why would Bonnet, a wealthy plantation owner, walk away from his marriage and life to sail around the seven seas?

There are a few possibilities for Bonnet’s mid-life crisis. First, he borrowed a large sum of money, the equivalent of about $400,000 today, which could point to a major loss with his crops or plantation. Second, one of his children died, which would be enough to ruin any parent. Third, he may have suffered from mental health issues. Or perhaps his wife was such a pain in the arse that isolating himself on a ship he couldn’t sail with a crew of foul-smelling men risking the noose was a relaxing option.

The show places him in a marriage of convenience to a woman content with life but not their arrangement. Likewise, Bonnet felt trapped in the marriage. He’s a wanderer at heart, idealizing what life on the high seas is. They do show him as a happy father though, perhaps more playmate than disciplinarian. The reality is, we will never know what drove him to abandon his family and forsake the law.

Bonnet and Blackbeard

What was his crew really like?

Contrary to the small crew featured on Our Flag Means Death, Bonnet’s crew totaled 70 men of questionable hygiene. His ship, the Revenge, was bought legally rather than commandeered (i.e. “stolen”) like other pirate entrepreneurs. Also unlike the show, Bonnet’s crew were actually skilled pirates, who helped him capture ships loaded with goods from the trans-Atlantic trade. He made quite a name for himself early on, thanks entirely to the skills of his smelly crew. (With all due respect to the now deceased pirates, they may have been very clean and took regular baths. My apologies.)

What was the real deal between Bonnet and Blackbeard?

Bonnet did meet the infamous Blackbeard, and the pair hit it off wonderfully. Blackbeard even invited Bonnet to sail around the Caribbean with him. I imagine this much like a bicycle gang patrolling the local neighborhood. The two leaders pedaling around striking terror into the hearts of the other kids on their bikes who just want to get to their friend’s house without getting beaten up. But it didn’t take Blackbeard long to figure out that Bonnet was inept. He seized the Revenge, locked up Bonnet on his ship the Queen Anne’s Revenge (the name “Revenge” for ships was very popular back then), and told him a gentleman would be more comfortable not commanding a crew.

Shockingly, this didn’t sit well with Bonnet, who plotted his, you guessed it, revenge. When Blackbeard marooned a third of Bonnet’s crew and abandoned Revenge, Bonnet took it back and vowed to take down Blackbeard. Sadly, he never got his chance at, um, revenge.

Bonnet and Blackbeard

So how did the real story end?

Blackbeard was killed battling the British Royal Navy on November 22, 1718. Bonnet was hanged for piracy weeks later, captured in South Carolina. The transcript of Bonnet’s trial remains one of the most detailed accounts of the life of Blackbeard and himself.

I don’t know if Our Flag Means Death will end in their deaths or not, but that would make a potential Season 2 challenging. While the first few episodes of the show struggle to find their sea legs, the introduction of Waititi’s Blackbeard elevates the show from a fun romp to a surprisingly deeper story. Darby’s and Waititi’s opposite energies make for on-screen magic, a product of working together in the same creative circles. HBO Max is releasing the season in three-episode installments, which always leaves me wanting more and anticipating each week.

For more on Our Flag Means Death, check out Watercooler Pick here.

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