Ching Shih might have been the most powerful and successful pirate in history. Born in 1775, she was brought up as a prostitute in the wanning years of the Qing Dynasty. As the ability of the central government to provide stability dissolved, ad-hoc mafia-esque alliances among profiteers arose, and piracy proved to be one of the most successful enterprises. Ching Shih’s first husband was from a pirating family, but when he married her, she became as active in the business as he. Her own prowess shone even more after he died about six years later – she expanded her fleet to command about 40,000 people (many of them families) with a fleet of 300 ships. The government was too weak to take her down, despite armed attempts. Her own governance was so complete she even issued her own pirate’s legal code – notably, it gave extremely harsh punishments if one of her men was found guilty of rape. Just as astonishing as her rise to power is Ching Shih’s ability to weather out her success – eventually, she accepted an offer from the government to retire that granted complete amnesty and the ability to keep all her wealth. She became a businesswoman on land afterwards, dying in her own bed at about age 69.
Source(s): Drawing of Chin Shih in battle (on the right) in the 1800s.