Obviously the Largest, Most Successful Pirate Fleet in History Was Led by a Woman

A few weeks ago, I made the reckless mistake of committing the swashbuckling souls of Anne Bonny and Mary Read to live on—perhaps forever—by “haunting” the seas. And just as you should never burn a Ouija board or tease the spirits, I appear to have summoned their ghosts, because they’ve since been haunting me in pretty much every dream. 

Alas, the next sensible thing to fight off the souls of Bonny and Read is to invite another pirate into my psyche, so here we are with yet another badly behaved woman of yore—and yes, another pirate: Zheng Yi Sao—the woman who commanded the largest pirate fleet in history. 

Zheng was born around 1775, during China’s Qing Dynasty (1636-1912), and grew up in Guangdong by the South China Sea. At the age of 26, she married a well-known pirate and, according to records, demanded that she get equal control of his Red Flag Fleet as a condition of their union. (The Red Flag Fleet was the largest of six pirate convoys at the time.) She became an essential part of the crew, and for reasons unknown, he then died about six years into their marriage. 

Technically, Zheng’s husband had an adoptive son slash heir (slash, er, lover) who was the next-in-line to control the Red Flag Fleet. But Zheng was able to convince him (slash, er, seduce him) to hand the right to her. She combined her men with the Black Flag Fleet (the second-largest group of pirates), the leader of whom (Zhang Bao) she convinced to join—so long as he got to be second-in-command. This put her in charge of 1,800 ships and anywhere between 40,000-60,000 pirates. No other pirate would ever sail the seven seas with such a large crew—significantly dwarfing the legacy of Blackbeard, the famed English pirate who had just four ships and a measly 300 pirates. 

Now in charge of a disgusting number of people, Zheng had to run, ahem, a tight ship—and implemented a new code of laws for her fleet. Any pirate who acted independently, gave his own order, or disobeyed his superior would be beheaded on the spot; no pirates were to go ashore without permission; and all loot was to be registered before it was shared. She also had a set of requirements for the treatment of women: any pirate who raped a female captive would be put to death and any pirate who had consensual sex with a female captive would be put to death along with the female captive. According to some records, the only way to get around this apparent guarantee of death would be to “purchase” and marry a female captive, and never cheat on her. Not a perfect feminist, but who’s counting!?

In its glory days, the Red Flag Fleet attacked ships from East to Southeast Asia, often attacking merchant vessels that were ferrying goods between China and Malaysia. It also fought off attacks from China, Portugal, and Great Britain—and in one instance, fought head-on with the Qing Navy (who had set a trap for her fleet), wiping out nearly half of the armada and commandeering a few boats at it. By 1810, however, she decided to retire on her own terms.

“She was absolutely, unquestionably the greatest pirate who ever lived,” Laura Sook Duncombe, who studies pirate women, told Atlas Obscura in 2022. “She pirated longer. She made more money. She surrendered of her own free will, got to keep her money, and live out the rest of her days in freedom, as opposed to being [cornered] and murdered by a government like Blackbeard was.” Wow, Girlbossmaxxing.

In exchange for keeping all the treasure they’d accumulated, avoiding any jail time or punishment, and being promised that the government would leave them alone, Zheng and her pirates peacefully retired after settling a deal with the Qing government. She lived comfortably before dying at the age of 69 in 1844—and never served one day in prison. But once an outlaw, always an outlaw—and she’s rumored to have lived out her days running a gambling house in Canton. Love a woman in business.

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