26. Ching Shih

Ching Shih, who lived and pillaged in the China Sea during the Qing Dynasty, has been called the most successful pirate in history (No, seriously! Google it!). A former prostitute from a floating brothel in the city of Canton, Ching Shih wed Cheng I, a fearsome pirate by family trade, and together they worked to unify the pirate bands against the Chinese and Portuguese Navy. At the height of her pirating days, Ching Shih commanded over 1,800 pirate ships, and an estimated 80,000 men – more than the famed Blackbeard within the same century. Embarrassing defeats for the Chinese Naval Armada, awkward possible ménage à trois with husband and kidnapped/adopted son, and one badass shrewd woman at the helm . . . this episode has it all!