8. Cheng I Sao Married Her Son
Cheng I Sao (1775 – 1844) worked the South China in the early 19th century and was probably history’s most successful pirate. A former prostitute, she married a powerful pirate, and inherited his outlaw realm upon his death. However, she was no mere widow who lucked into an inheritance: her own piratical legacy far exceeded that of her departed husband. Cheng commanded tens of thousands of outlaws, and despite challenging the British Empire, the Portuguese Empire, as well as the Chinese Qing Dynasty, she survived to end her days in peaceful retirement.
She was good at choosing capable subordinates, the most formidable of whom was Cheung Po Tsai (1783 – 1822), who was kidnapped in childhood by Cheng and her husband. Pressed into their crews, the teenager excelled in the new career suddenly thrust upon him, and rose swiftly through the ranks. Before long, Cheung had become the Chengs’ favorite, and was adopted by them as their son. When Cheng’s husband drowned, the widow took over his pirate fleet, married her adopted son, and made him her right-hand man.