From prostitute to powerful commander; this is the incredible story of Cheng I Sao – not only the most successful pirate (male or female!), but also the most badass ladyboss in history. Born close to the water in modern-day Guangzhou, the young Shi Yang understood early on that pearls don’t just lie on the seashore; you have to dive for them. And so she did! While working in a floating brothel, aka a ‘flower boat’, Shi caught the eye of pirate Cheng but would only marry him under one condition: that she would share equally in his power.

Together, they came up a with a winning strategy: to unite the ragtag pirates of the South China Sea to become a force to be reckoned with. Cheng died in 1807 but that didn’t stop Shi, now known as Cheng I Sao (Wife of Cheng). Thanks to her shrewd business sense and magnificent leadership skills, she amassed and ruled over history’s largest pirate fleet. Her 1200-strong armada with a total crew of over 70,000 men and women dominated over the South China Sea, wiping out roughly half of the Chinese navy in 1808.

Instead of spending her treasure as quickly as she received it – the traditional pirate way – Cheng I Sao branched out on the mainland; building her own banks, setting up a vast spy network etc. On her ships, rape was punishable by death. And if a pirate wanted to claim a female captive, he had to marry her and stay faithful, or he would be beheaded. Cheng I Sao basically established her own state, which she ruled with an iron fist and a feminist touch.

‘Madame Cheng’ decided to get out when she was still on top of the game. Surprising the government officials in 1810 by showing up to the negotiations with an assembly of unarmed women and children, she walked away from the surrender with her own treasures intact and a small fleet for private use. On top of that, most of her pirates were given not just amnesty but also civilian job. A crowning achievement for the Empress of Pirates.

And so, Cheng I Sao retired with her loot and her new husband (former righthand man, Chang Pao) and opened a gambling house. When she died peacefully in 1844, a 69-year-old grandmother, she had had the biggest fleet with the largest crews, made the most money and negotiated the most profitable exit in history. Yes, Cheng I Sao, the most successful pirate of all time, hadn’t left a single pearl unharvested.

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