Cheng I Sao was the most successful pirate of all times. Full stop. This is an objective statement. At the height of her reign, she commanded over 1200 ships and 80000 men and controlled all of the Chinese Seas. For comparison, the famous Blackbeard had four ships.
She was the embodiment of “from ratches to riches”. She grew up poor and had to work as a prostitute. Then, however, with cunning planning, she established herself at the top of the chain of command of the biggest pirate confederation of all times. Every part of her empire ran like an well-oiled machine: there was steady cash-flow from Mafia-like protection payments, ransom money and seized salt-trading. Even when her opponents combined forces, Cheng I Sao’s fleets defeated the British, Chinese, Portuguese and Dutch navies.
She also installed a famous code of conduct that catalogued appropriate punishments. Most notoriously? Anyone who raped a female captive would be beheaded. So was Cheng I Sao a feminist?
It is tempting to proclaim her the ultimate power-fantasy. But we know that there was also a punishment for having consensual sex with a female captive: you were still beheaded and she was drowned. (The only way to prevent that was to get married. Funnily enough, cheating on your wife would also get you beheaded.)
Now, we have to consider that there are very few reliable records of her life. Additionally, leading such a big empire probably meant she could show no weaknesses. All conclusions on her convictions are therefore speculative and she may have been a die-hard feminist at heart (but was unable to show it). Unfortunately, the most plausible explanation is that Cheng I Sao sold the female captives into forced prostitution. “Spoiling the goods” could therefore be seen as stealing from her- and would be appropriately punished. Selling women for money: not exactly what you would call a feminist.
Cheng I Sao was incredibly powerful. She was smart, managed her men and her empire with admirable wit and humiliated international powers with how easily she defeated them. The fact that she managed all that as a woman at the time is nothing short of mind-blowing. But she was also a pirate above all. She grew her empire by terrorizing people and exploiting anything that would benefit her. We cannot assume that she would stop from exploiting women, too. Allegedly, after her iconic retirement from piracy, she opened a brothel. I think this should tell us all we need to know. Cheng I Sao is a remarkable example of a powerful woman in history going after what she wanted. But we are projecting unjustifiably when we celebrate her as an feminist.