Stede Bonnet and his crew stand at the ready against a sky-colored background. In pink letters, the title reads "Our Flag Means Death."

Our Flag Means Death Works as a Retelling of Don Quixote

Our Flag Means Death’s Premise

From "Our Flag Means Death." Stede Bonnet stands next to a hapless crewman.
Stede Bonnet stands next to hapless crewman Oluwande – HBO –

“Gentleman Pirate” Stede Bonnet was a real pirate, although he was not one of the most capable figures from piracy’s golden age. An aristocrat turned to crime, he sacked ships and slit throats across the Caribbean. Briefly, he partnered with Blackbeard, though they later became enemies when Blackbeard looted Bonnet’s ship and marooned his crew. The law eventually caught with him and he was hanged on December 10, 1718.

That doesn’t sound like fertile ground for a situational comedy, but Our Flag Means Death succeeds through two tactics.

Firstly, it magnifies Bonnet’s cosseted background and the class tensions that must have caused between him and his men. For instance, Bonnet paid for his captaincy in cash rather than blood: his men received wages and he ordered his sloop from a shipwright. The show supposes, then, that he had a personality to match. He’s an amiable chap who knows that you use a fork to eat vichyssoise. The plot’s first villains are bullies from Bonnet’s preparatory school days. In short, he’s not merely a gentleman pirate, but a gentle man.

Secondly, it draws from the same wellspring of humor found in Don Quixote. Like the deluded knight errant, Stede Bonnet suffocates in the ennui of inherited luxury, seeks escape through books, and struggles to transform his life into the stuff of his favorite stories. The same imagination which sparks Quixote and show-Bonnet’s enthusiasm for fiction, however, drives them to delusion. Comedy arises from their inability to separate truth from illusion.

Our Flag Means Death and the Modern Comedy Landscape

Sitcoms have existed for thousands of years. Little of the sitcom’s individual components have seen alteration. The lazy lectus(couch)-surfer has always been in a script somewhere, as well as Big Misunderstandings and hidden identities. Although that results in a lot of repetition, the sitcom’s true strength lies in the sheer number of combinations it can produce.

For the longest time, however, a lot of those combinations were not available to the American sitcom. For complex cultural reasons, values began to skew conservative. Protocols like The Hays Code meant that sitcoms needed to hew rigidly to values like, say, the strength of the nuclear family unit. This intensified during the Cold War, when television became yet another front for a culture war between America and the Soviets. Fare like Diff’rent Strokes and Full House dominated the airwaves. M*A*S*H and Get Smart blazed trails which were acclaimed, but not followed. 

Our Flag Means Death demonstrates just how much that’s changed. It is the crest of a wave (pun intended) of high-concept ideas. Avenue 5 is a Space Titanic story. The Good Place is a divine comedy about the afterlife. The Great, in the grand tradition of Tom Stoppard, uses the setting of feudal Russia as an excuse for razzle-dazzle banter worthy of Rosencratz and Guildenstern Are Dead. All of these leave the more grounded observational humor of Friends behind.

A Portrait of Steve Bonnet

Stede Bonnet stands on the deck of his ship, the "Revenge."
Sketch of Bonnet from “A General History of the Pyrates” – Artist: Charles Johnson (1724-1736)

Back to Our Flag Means Death. Episode one opens and we meet a Bonnet floundering with a mutinous crew on the high seas, but that’s a trick of medias res. The real birth of the Gentleman Pirate begins with a bored Bonnet reading a book and sitting across a table from his wife, Mary. It’s clear they’re deeply unhappy with their arranged marriage.

His children, a son and a daughter, scamper around the house. Something valuable breaks. Mary begs him to play with them. Sighing, he agrees without a word – the body language of the deeply defeated. Before she leaves, she adds, “And don’t play ‘Pirates’ with them. They’ll have nightmares again.”

Once she’s out of sight, Bonnet roars and pounces on his kids. He digs out wooden swords and shields and spars with them. “I’m the greatest pirate who ever lived!” exclaims the timid domestic from ten seconds ago amid the clacking of wood on wood. For a brief moment, his spirit catches fire.

One night, his wife implores him breathe life into their dead union: “I know we wouldn’t have chosen each other, not in a million years, but all we have is this one life.” Her words have an effect, but not the one she expects. Leaving a brief letter behind, he gathers some money and flees during the night.

Later on, after he encounters Blackbeard, he pulls out a volume from his ship’s library (a feature another character rightly mocks as hideously impractical on the high seas). “Here’s one you might appreciate,” he says to Blackbeard. He flips to Teach’s entry in Howard Pyles’ Book of Pirates. It’s now clear where the disease started.

A Portrait of Don Quixote

A sketch of Don Quixote and his squire, Sancho.
Don Quixote and His Squire Sancho – Artist: Pablo Picasso (1881-1973)

The origins of Don Quixote (link to translation included) begin in much the same fashion. In La Mancha, Spain, there resides an elderly noble named Quesada.

[He was] one of those old gentlemen that keep a lance in a lance-rack, an old buckler, a lean [nag], and a greyhound for [hunting game]. . . . [He feasted on] more beef than mutton, a salad most nights, scraps on Saturdays, lentils on Fridays, and a pigeon or so extra on Sundays. . . . He had in his house a housekeeper past forty, a niece under twenty, and a lad for the field and market-place, who used to saddle the [nag] as well as handle the billhook.

He is a hidalgo, a type of petty aristocrat without ancestral lands. In other words, he’s in a permanent state of meager luxury with neither power nor desperation. He does not have to work to live, and he does not do much of importance.

This pushes him into a mid-life crisis. With time on his hands, he becomes a connoisseur of knightly tales. He sells his lands to buy more books about chivalry and neglects his estate grounds. Like a medieval Comic Book Guy, he debates the merits of various knights with the local curate and innkeeper.

The Birth of Don Quixote

An oil painting of Don Quixote astride his horse, Rocinante, and his squire, Sancho.
Don Quixote and Sancho Panza at a Crossroad – Artist: Wilhelm Marstrand (1810-1873)

Quesada’s mind consumes stories about knights like junk food and it deteriorates. In a fit of delightful snark, author Miguel de Cervantes implies that bad prose was the culprit.

But of all there were none he liked so well as those of the famous Feliciano de Silva’s composition, for their lucidity of style and complicated conceits were as pearls in his sight, particularly when in his reading he came upon courtships and cartels, where he often found passages like “the reason of the unreason with which my reason is afflicted so weakens my reason that with reason I murmur at your beauty;” or again, “the high heavens, that of your divinity divinely fortify you with the stars, render you deserving of the desert your greatness deserves.” Over conceits of this sort the poor gentleman lost his wits, and used to lie awake striving to understand them and worm the meaning out of [them.] Aristotle himself could not have made [any sense of it] had he come to life again for that special purpose.

Quesada hits upon an idea. Why can’t he become a knight? Thus, Quesada dies and his alter ego Don Quixote de la Mancha is born.

The Source of Dramatic Tension

Don Quixote kneels in the courtyard of the inn. Sex workers watch as the innkeeper knights him.
Don Quixote Believes He Is Receiving the Order of Knighthood at the Inn – Artist: Charles Coypel (French, 1694–1752)

The heroes of Don Quixote and Our Flag Means Death proceed to blend reality and fantasy. They enter into a childish frame of mind wherein the common and the extraordinary mix. The way in which they do so differs, however. Don Quixote imbues the everyday with his fantasy, whereas Bonnet tries to tame his fantasy with the more mundane aspects of his old life. 

In both cases, this results in disaster. Their situations resist their wish fulfillment and threaten to consume them. 

Don Quixote’s Active Imagination

Don Quixote, for instance, supposes that a knight must have a maiden to dote on, so he dedicates himself to “Dulcinea del Taboso,” a sex worker he regularly patronizes. He rides his poor nag, Rocinante (Spanish for “workhorse”) like she’s a stallion, and she collapses under his gallant charges. He draws others into his pageantry, like Sancho Panza, his poor servant turned squire, and they inevitably suffer.

During his first sally, for instance, he approaches an humble inn, which his addled brain dubs a castle. He asks the innkeeper, who he believes to be a lord, to knight him. The innkeeper, a strangely well-read man and a practical joker, plays along and promises to knight Don Quixote tomorrow. In the meantime, he commands Don Quixote to stand vigil over his armaments in the inn’s courtyard, as the knightly stories dictate. While he does so, the innkeeper points him out to his customers and shares a laugh at Quixote’s expense. To onlookers, Quixote is simply a fifty-year-old man in his father’s trashy armor. 

But then stablehands and workers enter the courtyard to draw water from the inn’s well. They move his armor in order to use the cistern. Protecting his honor, Don Quixote knocks them out one-by-one until they overwhelm him. In the end, the innkeeper has to quote some obscure (probably made up) technicality to cu the vigil short, knight Quixote early, and send him away. 

Our Flag Means Death

Bonnet’s issues express themselves differently. Instead of confusing normalcy for piracy, he believes that he can approach piracy like a normal job. As mentioned before, he pays his men in wages and not booty. He claims books as plunder and swaps them with some of his own, acting like he’s in a communal library program. When the Revenge runs aground, he tells his crew to take a “vacation,” as if a gang of murderers would understand the concept of a spa day. His sailors complain about the lack of a proper Jolly Roger. In response, Bonnet organizes them into a knitting circle and tells them to vote for their favorite flag. 

This reflects a key distinction between the real-life Bonnet and the fictional Don Quixote. Pirates were still in their heyday when Bonnet walked the Earth. Conversely, knights were as distant a memory to Cervantes’ audience as human pinsetters are now. 

Enemies of the World

Nevertheless, the chief antagonist of both remains the same: the world. Bonnet and Don Quixote envision a better, nobler law than reality will allow. Their struggles represent the fallen nature of our society. 

After the inn, Don Quixote encounters a farmer mercilessly whipping one of his fieldhands. Outraged, he menaces the farmer with his lance and demands restitution for the fieldhand. The farmer agrees, though he protests that he has no money with him. Don Quixote extracts a promise and vows he will return to enact vengeance if it is not honored. The farmer gives his word. The fieldhand warns Don Quixote that his master lies, but the knight ignores him. Don Quixote rides into the sunset, priding himself as a righter of wrongs. 

Predictably, the master immediately reneges and whips the fieldhand to near-death. Don Quixote’s idols led him to believe in a just world, but brutality prevails. 

For Bonnet, his attempts to impose gentility on piracy undo him. Exasperated by Bonnet’s naivete, his crew buck at his authority, mutiny, and disparage him. The pirate world will not permit his virtues or the prospect of a kinder lifestyle. 


The unifying force behind Bonnet and Don Quixote, then, is unyielding idealism. Their struggle mirrors our own astonishment at the rewards that evil reaps and goodness’ inability to thrive. Their persistence and failures in that regard represent our own, often unwinnable pursuit of the proper shape of the world.

Don Quixote‘s resolution, however, takes a cynical view of these themes. After countless defeats, Don Quixote comes to his senses and reverts to fifty-year-old Quesada. He swears off knightly literature and forbids his niece from marrying anyone who likes them. The world bests him. 

Conversely, the current state of Our Flag Means Death points toward a more optimistic outcome. Besides adding a welcome splash of LGBTQ diversity, the series finale suggests that Bonnet’s worldview can be infectious or even transformative.  Faith, like sand, can accumulate even with failure. It can bring the world in alignment with our Don Quixotes and Stede Bonnets. I don’t wish to fully spoil its developments in this space, so I apologize for that cryptic description. 

Of course, history knows that the gallows still loom over Bonnet, but don’t let that spoil the fun. 

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