One of the most successful pirates in history was Zheng Yi Sao, a Chinese woman. Historians aren't clear about her early life; she may have been a prostitute. But in her twenties she married a pirate lord who commanded a large confederation of pirates, and thus lived a live of piracy with him for years. When he died in the early1800s, rather than the confederation turning to chaos, she managed to take command of it. She married her late husband's adopted son Zhang Bao as well (she was in her 30s, he in his 20s), and he became basically the #2 in the fleet under her, and that helped cement things. Over the next few years, the confederation grew to hundreds of ships and tens of thousands of pirates. They were one of the biggest powers in the South China Sea, rivaling the navies of China, Portugal, and Britain who were active in the region. In 1810, however, she saw that the future probably wouldn't be so bright for her and the pirates. A pirate confederation is a chaotic thing, and cannot last against multiple navies indefinitely. But pirates rarely ever quit while they're ahead; they almost all end up dying violently. The Chinese and other navies were working together and were pretty desperate to get rid of piracy, and were willing to negotiate. However after months, negotiations broke down between the authorities and the various pirate lords, including Zhang Bao, until Zheng Yi Sao went personally to the Chinese governor's mansion that they were primarily negotiating with, at great personal risk. Just walked right in there with a small delegation, without any fighting force, to negotiate, and got it done. After that, the pirates surrendered from a position of strength. Zheng Yi Sao, Zhang Bao, and others received pardons and got to keep most of their wealth. Zhang Bao became an officer in the Chinese navy, commanding a fleet like he used to. Zheng Yi Sao received land and founded a gambling house. Their marriage was recognized by the Chinese government, having been an unofficial "pirate marriage" beforehand. Zhang Bao eventually died age 39, still in service in the navy. Zheng Yi Sao died at 68, having lived decades overseeing her gambling house, and with children from both her marriages. A pirate lord that retired wealthy and peacefully, and managed to navigate the transition away from piracy in a way that let the most reasonable pirates all quit while they were ahead. https://en.wikipedia.org/wiki/Zheng_Yi_Sao