The Most Successful Madam in America

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Rudyard Kipling called sex work ‘the oldest profession’, but the odds of growing old in that profession are and always were vanishing small. Disease and violence, persecution and prosecution have haunted sex work from the beginning of time. Historically, if a person was in the sex work trade, they had a much better chance of living to a financially successful old age if they graduated to management. For women who started from nothing, who had no other way to earn a living, it was a dangerous path to maybe a fortune. It took guts and brains and business sense. It took immense social savvy. One of those women, with a spine of titanium and nerves of steel, maybe the most successful of madam in North America, lived in Natchez, Mississippi.

Nellie Jackson was born in 1901 in the less-than-salubrious Possum Corner, Mississippi. To say the odds were against a dirt-poor woman of color is gross understatement. She went from that seriously inauspicious beginning to a section of Natchez they call Under The Hill. When Natchez Under The Hill is a step up? That’s about as bad as it gets.

Natchez is maybe the most Southern town in the whole of the deep South, with everything that entails. It’s a Mississippi river port littered with slowly decaying, genteel mansions built by slaves. It went bust at the turn of the 20th century when the boll weevil hit. It went bust again in the Great Depression. Natchez-Under-The Hill was, in those days, extremely dangerous. Violence was a daily occurrence, and prostitution was one of the most at-risk professions. People who were unwary or stupid… well, the Mississippi is deep and silent, and her mud is laced with rotting bones.

Nellie Jackson wasn’t about to live a short life of misery Under The Hill. The US was entering the Great Depression by the time she’d made enough money to buy a nice house in a respectable neighborhood. 416 North Rankin Street became ‘Nellie Jackson’s’ in 1930, and her black book was open for entries. She had strict rules. No drugs, no drunks, no violence, absolute discretion, and she catered only to white men. In the 1930’s it wasn’t safe to do anything else, and she understood that. Nellie cultivated safety. She understood the rules, both spoken and unspoken, of the society around her. She never, ever recognized anyone on the street unless they spoke to her first.

The women who worked for her—of every ethnicity and skin tone, so the customer could have whatever he wanted—would stay for three or four weeks at a time before moving on. Her house was part of a circuit of ‘boarding houses’. They never stayed long enough to create entanglements, even though they rotated back to 416 Rankin time after time. Some women worked there as weekenders between other jobs in other cities. Some married women worked there when their husbands were working offshore or were out of town. They were, one and all, exceptionally easy on the eyes. And they brought in money. Lots of it. Nellie’s accountant revealed after her death that she’d owned at least two other ‘boarding houses’ in other cities.

Looking respectable on the exterior was a key requirement. She made sure 416 was always neat as a pin, and that every residential house on the street was as well. If a house on Rankin Street needed paint? She’d send someone to paint it. She paid good wages for the chores that the ‘boarding house’ needed done—cleaning and laundry and upkeep. She dressed beautifully. On Halloween when other neighborhood houses gave out candy, Miss Nelly gave out rolls of quarters. She kept poodles. She gave with massive generosity to a local program for abused children, to the Catholic Church, to every charity in town. She put her relatives and half the neighborhood through college. Miss Nellie’s neighbors adored her. She took the mayor a yearly Christmas gift of booze, and baked birthday cakes for the police. There were other bordellos in Natchez, but those got raided. Not Nellie Jackson’s.

It became a tradition to take young men about to be married for a night at Nellie’s as part of his bachelor party, ‘to be sure they’d know what they were doing’. When an army base opened near Natchez during World War Two, the line from her door could stretch for three blocks on Saturday nights. Every politician who passed through Natchez stopped at Nellie’s. She was friends with Bill Harrah, who owned the high-end casinos in Reno and Las Vegas, sent her yearly first row tickets for the World Series.

In spite of her caution, Nellie’s wasn’t immune to violence. In 1957 one of her girls was murdered, her throat slit. Nellie took one glance, realized the woman was dying, and drove the murderer out with a chair. People criticized her for not rendering aid immediately, but there were other women in that house, and Nellie was having no chance of anyone else being hurt. Nellie spent some time in jail, but by then nearly every white man in power either knew Nellie or had been to Nellie’s. The mayor, the police chief, and every cop in Natchez knew her. They let her out as soon as they reasonably could.

During the Civil Rights era, when law enforcement in Natchez arrested hundreds of protesters, many of them children, Nellie waded into the police department and got sentences reduced, charges thrown out, or bail paid. It put her life and profession at risk, but her famous black book contained every powerful man in Natchez. And she went further. KKK members in the area came to Nellie’s just like every other white man in the area. The irony of that aside, they talked to the women they bought time with. Just before dawn on many, many nights, two agents of the FBI would slip in through the famous kitchen door and be invited up to Miss Nellie’s room. And names started to be printed publicly in the paper and the clan in the area broke up or at least went far less public.

When the days of tee-shirts came around, every bar in town had tee-shirts with slogans featuring Nellie Jackson’s. Those tee-shirts, many on military men, traveled Europe and around the world.  Her family urged her to retire, but she ran her ‘boarding house’ until 1990.

One night she turned away a belligerent drunk, judging him to be trouble. She was right. He went and bought a cooler, filled it with gasoline, and got it all over himself carrying it back to the house. When he knocked, Nellie met him at the door with a pistol. He threw the gas on her, threw a lighter at her and set both of them on fire. She died of her burns, and an era passed with her.

In a world that might’ve ground her in more rotting bones in the mud of the river, Nellie Jackson fought for survival and made it past what anyone could’ve predicted. Her funeral took place in the Catholic church over the vociferous objections of some of the ‘upstanding’ people of Natchez. Father O’Connor said that no one had the right to judge Nellie Jackson, scalded his parishioners in a sermon on rendering judgement, and spoke of all the good she’d done.

Nellie Jackson made it a long time before violence claimed her. Thirty years later, there are still people who’d like to know where her black book has gone. Nellie’s niece just smiles, and quotes what Nellie used to say when asked her age—“That’s a military secret.”

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IMAGE CITATION: from the documentary MISSISSIPPI MADAM: THE LIFE OF NELLIE JACKSON (2017)

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