As the 19th century loomed, China experienced a huge boom in piracy—and the largest, most terrifyingly organized fleet that menaced the South China Sea was led by…a woman. Madame Cheng (remembered as Cheng I Sao or Ching Shih) had a meteoric rise from impoverished sex worker to climb to arguably the most successful and influential pirate of all time. Should we cheer her on—or remember her as a criminal? 

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