Among history’s most notorious characters, none capture the imagination like pirates. From the freedom of the high seas to treasure chests spilling over with plundered loot, the escapades of pirates have inspired generations of storytellers and bartenders alike. While sipping classic rum cocktails like Daiquiris and Mai Tais, it’s not hard to see why rum has been the toast of the tropics for centuries, or why it was so popular with pirates from the Barbary Coast to the Caribbean. Popular culture doesn’t tell the whole story, though, and the truth about pirates’ affection for rum is an interesting tale of its own.

While as a brand pirates don’t typically conjure images of safety first, their affinity for rum was surprisingly practical. Like many spirits, rum has medicinal origins, and it was frequently used for its curative properties–not just by pirates, but by everyone who made a living sailing the high seas. Much like their scallywag counterparts, sailors in the British Royal Navy also used their daily ration of rum to ward off disease and to treat a variety of ailments ranging from digestive complaints to scurvy. 

Maintaining a plentiful supply of rum on board was considered a necessity in the era before modern medicine and water filtration. Water on long sea voyages doesn’t stay potable for long, and access to rainwater couldn’t be counted on during long sea voyages. The solution? Grog. Part medicinal, part cocktail, grog was a mix of water, rum, and lime juice thought to prevent dehydration while also preserving the fresh water supply. Pirates drank it by the barrel, and today many cocktail historians cite it as an early version of the Daiquiri. 

Beyond its general curative properties and contributions to water quality, rum was a sound business strategy for pirates in the 18th and 19th centuries. While trunks full of gold and jewels were hard to come by–despite what all those X-marks-the-spot treasure maps in books and movies have led us to believe–ships on Atlantic trading routes were frequently laden with casks and barrels of rum. Though we imagine significant portions of plundered rum were held back for pirates’ personal supply, the lion’s share went to commerce and trade, keeping buccaneers flush in parrots and pirate hats.

Like pirates themselves, rum has long been associated with–and celebrated for–acts of defiance and rebellion. Rum was the reason for early bootlegging efforts when it was subjected to exorbitant taxes imposed by the English crown as part of the Sugar Act of 1764, and it became prized on the black market. A sign of the prohibition acts that would be enacted over a century later, these taxes led to a brisk trade in underground rum markets, which were made possible through piracy and only added more layers to the richness of pirate lore. So the next time you’re enjoying a frosty rum punch, raise a glass to the pirates of yesteryear and drink up, me hearties, yo ho!