Weird History The Most Successful Sex Workers In History  

Genevieve Carlton
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The most successful sex workers of all time beat the odds and rose to positions of enormous wealth and power. Some were born into slavery or raised in brothels, while others chose sex work for social advancement. While many sex workers in history worked multiple jobs and had to fight off violent clients, these professionals used their skills to gain wealth, status, and respect. These women succeeded against the odds, earning them a spot on the list of most successful sex workers of all time.

Unlike today's high-end escorts, in the past sex workers often didn't choose to go into the profession. Chica da Silva was born into slavery, while the mother of Charlotte Hayes was a brothel madam who auctioned off her daughter's virginity. One former prostitute became history's most successful pirate, while an exotic dancer rose to become empress of the Byzantine Empire. Wherever they might have started, these women reached impressive climaxes in their careers.

Ching Shih is listed (or ranked) 1 on the list The Most Successful Sex Workers In History
Photo: Unknown/Wikimedia Commons/Public Domain

In the early 1800s, a former prostitute managed to transform herself into a pirate queen. Ching Shih worked on a floating brothel in Canton – until she took over her pirate husband's business, that is. At her peak, Ching Shih commanded over 1,800 pirate ships and led 80,000 men, vastly exceeding the famous Blackbeard, who had only four ships with a crew of 300 pirates. 

Ching Shih used her experience as a prostitute to manage the enormous fleet, creating her own pirate code of laws. The strict code ordered death for pirates who raped female captives. During Ching Shih's reign, her pirate fleet went undefeated against the Qing dynasty, the Portuguese navy, and the East India Company. Ching Shih negotiated amnesty with the Chinese in 1810 and lived another 34 years in retirement.

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Charlotte Hayes is listed (or ranked) 2 on the list The Most Successful Sex Workers In History
Photo: Author: John Harris; Engraver of frontispiece: John June/Wikimedia Commons/Public Domain

Charlotte Hayes's Themed Orgies Made Her Rich

In the 1700s, sex worker Charlotte Hayes rose from the bottom rungs of society to become one of the wealthiest self-made women in London. Hayes's mother was a madam, and the young girl was raised in a brothel. When she reached her early teens, her mother tried to sell her virginity. Once she struck out on her own, bad luck landed Hayes in debtor's prison.

Yet she managed to claw her way to the top despite this trouble: she opened several luxury brothels, decked out with expensive furniture and chandeliers, catering to London's richest men. The brothel was known for its theme parties, including a Tahitian orgy and a Grecian orgy. Each visitor easily dropped the equivalent of thousands of dollars a night, transforming Hayes into one of the richest sex workers ever.

Theodora is listed (or ranked) 3 on the list The Most Successful Sex Workers In History
Photo: Meister von San Vitale/Wikimedia Commons/Public Domain

She's been called the empress from the brothel. In the 6th century, Theodora rose from the ranks of an exotic dancer all the way to empress of the powerful Byzantine empire. Theodora was the daughter of Constantinople's bear-keeper, and by age 15 Theodora was a star of the hippodrome, performing burlesque dances before cheering crowds. Procopius, a contemporary historian, even described the empress's early career dancing naked with only a ribbon for cover.

At 21, Theodora caught the eye of the emperor's nephew, Justinian, who literally changed the empire's laws so he could marry Theodora. Once she became empress, Theodora fought for the rights of sex workers, setting up a house for former prostitutes and championing anti-rape laws. She also banished all the brothel-keepers from Constantinople. 

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Ninon de l'Enclos is listed (or ranked) 4 on the list The Most Successful Sex Workers In History
Photo: Antoine-Jean-Baptiste Coupé/Wikimedia Commons/Public Domain

Ninon de l'Enclos Gave Men And Women Lessons In The Art Of Love

In the 1600s, famous French courtesan Ninon de l'Enclos counseled women on how to sleep around, telling them, "A woman who has loved but one man will never know love.” In her young years, l'Enclos vowed to never spend more than three months with a single lover, but after she retired from being a courtesan, l'Enclos founded an informal academy to give men lessons on how to please women. She also taught noble women the art of love for free. Her reputation was such that even Louis XIV was known to ask "What does Ninon think?" before changing mistresses.

L'Enclos also supported writers and struggling artists, even leaving money in her will to help the young Voltaire, who just so happened to be the son of her accountant.