It’s a tale as old as time. Boy meets ocean. Boy takes a dip in Havana harbor. Shark says, “Snack time.” What follows is arguably the first documented shark attack in Western history—unless you count every sailor’s tall tale ever—but more importantly, it’s the only one immortalized with the flair of 18th-century drama and a shark with… lips?

One Leg, Nine Rescuers, and a Whole Lot of Shark Drama

Our unlucky protagonist is 14-year-old Brook Watson, a cabin boy who, in 1749, decided to go for a swim in Havana, Cuba. Cue the ominous cello music—enter stage left: shark. What kind of shark, you ask? Experts now say it was probably a tiger shark or a great white, but in 18th-century artistic tradition, it was… whatever a shark would look like if painted by someone who had never seen one before.

The shark attacked young Brook not once, but twice. It chomped off his right leg below the knee and was reportedly coming back for thirds when a boatload of crewmates managed to drag him out of the water. This scene—gruesome, heroic, and apparently lacking any concern for shark anatomy—was immortalized decades later in a painting commissioned by Watson himself. Because when you survive a shark attack and lose a leg, what you really want is a giant oil painting to show everyone just how close your femoral artery came to becoming fish food.

The Painting That Bit Back

Watson commissioned American artist John Singleton Copley to paint the scene in 1778. The result, Watson and the Shark, became an instant sensation—and also an instant case study in marine biology by way of speculative fiction. The shark in the painting has lips (yes, actual lips), front-facing eyes (like a wolf, but wetter), and an expression that suggests it may be late for a dinner reservation. Copley had never seen a shark, so he did what any artist might do: he winged it. The result is either horrifying or adorable, depending on your feelings about anthropomorphic sea creatures.

The painting features nine men attempting to rescue Watson, most of whom seem dramatically confused or spiritually conflicted about what exactly to do with their oars. One figure, a Black sailor holding a rope, is especially striking. Some scholars believe he was included intentionally to emphasize the humanity of Black men at a time when abolitionist ideas were starting to gain traction. Others think he’s just there because someone had to throw the rope. Either way, the man looks like he knows what he’s doing, which is more than we can say for some of the other crew members who appear to be engaged in synchronized flailing.

Shark Bites and Social Clout

After surviving the attack, Watson went on to live a legendarily successful life. He became a wealthy merchant, Member of Parliament, and eventually Lord Mayor of London. Take that, Sharky. He made sure his amputated leg didn’t keep him down—unless, of course, he was falling down a flight of stairs, in which case… well, we all have our limits.

Watson’s choice to commission the painting wasn’t just an act of personal catharsis; it was branding. “Look at me,” it seemed to say. “I lost a leg and still beat the odds. Also, here’s a great example of why you shouldn’t swim unsupervised.” The painting was donated to Christ’s Hospital School in London with a note that it should serve as “a most usefull lesson to youth.” That’s right—nothing says moral education like a child being devoured by a sea monster with kissing lips.

Was This Really the First Shark Attack?

Technically, no. Archaeologists have discovered shark-bitten human remains in Japan dating back 3,000 years and in the Caribbean from around the 9th century. So while Watson’s run-in may be the first documented shark attack in the sense that it came with an oil painting and a moral lesson for the kiddies, it’s far from the earliest.

Still, it’s the first one to feature a nine-man rescue team, theatrical posing, a shark with human lips, and a future Lord Mayor. So, historically speaking, it’s got flair.

Moral of the Story? If It Ain’t Baroque, Don’t Fix It

If you’re going to be eaten by a shark, make sure it happens in dramatic fashion, ideally in full view of multiple rescue boats. Bonus points if you can later commission a baroque masterpiece that redefines marine zoology and earns you political clout. Or, you know, maybe just stick to the pool. And since New Yorkers have a tendency to bite more frequently than sharks, you might want to avoid swimming in the Big Apple altogether.

Watson may have lost a leg, but he gained a legacy—and a permanent spot in both art history and our collective “bad decisions near water” file. Somewhere out there, a shark with a lip gloss addiction is still wondering what went wrong.

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