Cheng I Sao (Chinese, 1785 – 1844)
Now merge all ships and vessels of previous nine pirate captains in this list, then gather all pirates and sailors they had, and you couldn't have nearly enough power to beat mighty fleet of beautiful captain, Cheng I Sao.
In the height of her power, former prostitute controlled more than 1,500 ships and had the manpower of 80,000 sailors which was one of the biggest naval armies in the history of the world. This female pirate captain used her super large army for robbing and taxing towns and plundering ships throughout the coast of the South China Sea.