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The real-life gentleman pirate behind HBO Max’s new series Our Flag Means Death

A nervous man in 18th-century garb.
Enlarge / Rhys Darby stars as gentleman pirate Stede Bennett in the upcoming HBO Max comedy series Our Flag Means Death.

It’s no secret that Ars staffers are big Taika Waititi fans. He always brings his distinctly quirky sensibility to his projects, from What We Do in the Shadows, Wellington Paranormal, and Hunt for the Wilderpeople, to JoJo Rabbit, Reservation Dogs, and Thor: Ragnarok. After filming wrapped on Thor: Love and Thunder last year, Waititi somehow found time to develop a new period comedy series for HBO Max.

It’s called Our Flag Means Death, and HBO just dropped the first teaser. The series is about an aristocrat who abandons his comfy life to become a “gentleman pirate.” Even better: the main character, Stede Bonnet (played by Rhys Darby) is based on a real person who sailed with the infamous 18th-century pirate Blackbeard (played by Waititi in the series).

The real Stede Bonnet was born on the island of Barbados in 1688 to a wealthy English family and inherited a 400-acre estate when his father died in 1694. By some accounts, he was a bookish sort, and his early life was unremarkable. He married, fathered three sons and a daughter, and briefly served in the military as a major, although there is no record that he engaged in active combat.

But at 29, Bonnet experienced some kind of midlife crisis and decided to abandon his family and become a pirate, even though he had zero experience with ships and sailing. Apparently, he was fed up with his wife’s nagging, or as one account put it, he became disillusioned with the “discomforts he found in a married state.” Most pirates seized their ships; Bonnet was a man of means, so he hired a local shipyard to build him a 60-ton sloop with 10 guns. He dubbed the ship Revenge and hired a crew of more than 70 men. Bonnet actually paid the men regular wages rather than splitting plunder with them like a normal pirate.

Bonnet's motley crew is ready to loot and plunder.
Enlarge / Bonnet’s motley crew is ready to loot and plunder.

YouTube/HBO Max

Given Bonnet’s lack of experience, much of the day-to-day sailing operations were handled by his quartermaster and officer, and he doesn’t seem to have won much respect from his crew over the course of his short pirating career. (In fairness, piracy was a dangerous profession and few pirates lived to a ripe old age.) The piracy went well at first: the Revenge captured and plundered some half-dozen vessels between spring and September 1717. But a battle with a Spanish man-of-war left both Bonnet and the ship in a bad way, although both ultimately escaped.

The Revenge next limped into port at Nassau in the Bahamas for repairs, which is when Bonnet met Blackbeard, aka Edward Teach. Given the disabling nature of his injuries, Bonnet ceded command of the Revenge (temporarily, he thought) to Blackbeard. For the next few months, they plundered a lot of ships, and Blackbeard seized and took command of a 200-ton vessel called La Concorde, which he renamed Queen Anne’s Revenge.

Eventually, Bonnet’s frustrated crew deserted him and joined Blackbeard in the spring of 1718, and Blackbeard betrayed Bonnet, placing one of his own henchmen in charge of the Revenge. By now, Bonnet longed to retire from the pirate life, and he actually received a pardon from the governor of North Carolina on condition that he renounce piracy forever. Bonnet tried to keep his promise, but food became scarce right as the Atlantic hurricane season was in full swing, so he resorted to piracy once again under the alias “Captain Thomas.” He gave Revenge a new name, too: Royal James.

Taika Waititi co-stars as Blackbeard.
Enlarge / Taika Waititi co-stars as Blackbeard.

YouTube/HBO Max

All the battles once again took their toll on Royal James, and after it was repaired, Bonnet decided to moor in the Cape Fear River to wait out the hurricane season. News of his presence soon spread to the relevant government authorities, sealing the gentleman pirate’s fate. Bonnet and his men put up a fight against Col. William Rhett’s naval forces, but they lost, and the entire crew was arrested on October 3, 1718. Bonnet was convicted and eventually hanged (after briefly escaping and being recaptured) on December 10, 1718. All told, Bonnet’s life as a pirate lasted less than two years. Then again, if he had just stayed in Barbados and lived out a life of quiet desperation, we likely would not know his name.

Bonnet’s mentor, Blackbeard, didn’t fare much better. In November 1718, just one month before Bonnet was hanged, Teach and his crew engaged in a fierce battle with a small group of sailors led by Lt. Robert Maynard. Eventually, Teach found himself surrounded by Maynard’s men, one of whom slashed him across the neck before the rest of the crew joined in the attack. When Maynard examined the body, he found Teach had been shot five times and cut some 20 times. His head was placed on a pole in Chesapeake Bay for several years to serve as a warning for other pirates.

Based on the teaser for Our Flag Means Death, the series is unlikely to attempt much in the way of historical accuracy, which is the right decision. Tonally, it evokes something along the lines of Hulu’s extraordinary period comedy series, The Great, which takes historical characters and facts and embellishes them, complete with the odd deliberate anachronism. (The credits for The Great claim the show—just renewed for a third season—is “an occasionally true story.”) The Great is a high bar to clear, but this is Taika Waititi we’re talking about, and we have faith in his idiosyncratic vision. We’ll definitely be tuning in.

Our Flag Means Death debuts on HBO Max in March.

Teaser for HBO Max’s new original comedy series, Our Flag Means Death.

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