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In the fall of 1895, Madam Priscilla Henry lay on her deathbed in one of the lavish bordellos that she’d used to entertain patrons for decades. The premier lady of sex work in Victorian St. Louis had built an empire estimated to be worth at least $100,000—the equivalent of about $3.7 million today—but she seemed remorseful over her dealings and fate as her health waned.

“She was often heard to remark that her sufferings were a heavenly visitation sent upon her as a punishment for her sinful life,” the St. Louis Post-Dispatch reported. Plenty of people in the Missouri city agreed with Henry’s own harsh assessment.

“Wicked, Notorious, Old Priscilla Henry Is Dead,” chastised the supremely blunt headline in the Post-Dispatch, decrying the madam’s career as “Pandering to Depraved Passions.”

Yet the 76-year-old Henry had her defenders, too. She rubbed shoulders with some of the most prominent people in St. Louis, and the vitriol that met her death was balanced by outpourings of praise. Even the Post-Dispatch, which branded her “the wickedest wench in St. Louis,” had to admit that “the deceased was one of the most remarkable women of her class that ever lived” in the city.

The end of Henry’s life stood in stark contrast to how it began. The woman who successfully set up a business empire, collecting wealth and property by captivating men from across social classes, began life enslaved, with not even freedom to her name. She ended it not only as an infamous bordello madam who outsmarted a long line of competitors and connivers who sought to bring her down. She also did an extremely rare thing in American history: She used the fortune she’d amassed to buy the very Alabama-based plantation where she was born, enslaved and raised. But danger seemed to follow Henry everywhere she went, and she would ultimately pay a high price for her remarkable success.

The making of Madam Henry

Henry migrated to St. Louis from Alabama in the 1860s. The full-figured woman with a commanding presence was the eldest of six children. She spent the first 46 years of her life near the city of Florence, Alabama, on the Forks of Cypress Plantation owned by slaveholder James Jackson Jr., who initially refused to free the individuals he’d enslaved after the Emancipation Proclamation was signed.

Once she was finally granted news of her freedom, Henry traveled north to “Mound City”—as St. Louis was known—by flat boat, where she had brief stints working as a maid and a washerwoman. But Henry quickly discovered one of city life’s timeless dirty secrets: Sex sells.

The Social Evil Hospital
The Social Evil Hospital was founded in 1873 as part of the Social Evil Ordinance, which legalized and regulated sex work in the city. After the ordinance was repealed, the hospital opened to treat poor women and children in the city. Courtesy of the Missouri Historical Society, St. Louis

As in other river towns, particularly Kansas City and Memphis, the escort industry in St. Louis capitalized off travelers whose business took them down the Mississippi and Missouri Rivers. The Gateway to the West became a hotbed for prostitution in the late 19th century, so much so that it was one of the first cities in America to temporarily legalize the business. The Social Evil Ordinance of 1870 required St. Louis-based sex workers to pay a fee to become licensed employees in licensed brothels, in addition to covering the costs of weekly medical checkups by a certified doctor and any administered medications. Those who failed to pass the examination were confined to the Social Evil Hospital for treatment.

The Social Evil Ordinance was short-lived—it was repealed in 1874—yet the oldest profession continued to thrive as the Gateway to the West expanded its reign as a bustling port along the Mississippi. The city became home to well-connected aristocrats and entrepreneurs, as well as an ethnically diverse population of immigrants and Black Southerners who traveled there in search of a better life.

St. Louis also increasingly faced a societal challenge experienced by many booming metropolises during the Reconstruction era: the rise of an impoverished population bred by the exploitation of working-class minorities. Crime, vice and desperation plagued the cobblestone streets of Soulard Market, a lively neighborhood just two miles south of downtown. Disillusioned Civil War veterans, fugitives, the formerly enslaved and thrill-seekers filled Soulard Market and other nearby neighborhoods, hungry for their piece of the sparkling spread of saloons, gaming halls, dance houses, barber shops, speakeasies, produce stands, regal estates and architectural motifs—everything that represented the buzzing illusion of opportunity.

One of those have-nots was Henry. She first settled into working downtown as a maid at the Lindell Hotel, once the largest hotel in North America, with 530 rooms spanning six stories. There, Henry cleaned toilets and spittoons in exchange for room and board. Unreasonably heavy workloads and long working hours were typical for Black women of her status.

Then, on March 30, 1867, fate stepped in.

The Lindell Hotel burned to the ground. And, likely having no other options, Henry moved into a “boarding house” for Black women (then a euphemism for a place that housed wayward women of the night) and made a living doing laundry—while selling her “goods” on the side.

There, she met Tom Howard, a white ex-Confederate soldier who had suffered a brain injury during the war. Howard ultimately became Henry’s lover and financial backer for over two decades, helping as she made the transition to brothel mistress, in charge of overseeing the nightly rendezvous between working girls and patrons.

Henry eventually opened two bordellos on Sixth Street, the heart of St. Louis’ red-light district. One location was for Black prostitutes, and the other for white prostitutes. Both houses served white men, but Missouri’s anti-miscegenation laws only allowed Black men to seek companionship at the bordello where Black escorts worked.

The heart of St. Louis’ red-light district on Sixth Street
The heart of St. Louis’s red-light district on Sixth Street, between Washington Avenue and Market Street, as mapped in 1895 Library of Congress, Geography and Map Division

The sex-segregated labor market in St. Louis during the 19th century was doubly demoralizing for Black women. Henry was likely the first Black female sex entrepreneur in town, and she surely experienced unfair treatment, navigating racial discriminatory practices—written and unwritten—as she worked to get her business off the ground. While Black sex workers typically earned less than their white counterparts, Black bordello owners like Henry were also typically forced to charge less for services than white proprietresses.

Despite this, the flesh havens on Sixth Street soared to unthinkable heights, and Henry’s business boomed. According to the Post-Dispatch, she was soon known “from New Orleans to Minneapolis, and even to those whose avocations called them to the most remote points in the interior along the turbulent Missouri.” Her success was credited to the fact that she was “naturally a good caterer and a woman who wanted to please.” The Post-Dispatch continued:

She attracted the semi-respectable men who drifted to and from St. Louis with the seasons—the gamblers, the horse-traders, the steamboat captains, mates and engineers, and in time, the name of Priscilla Henry was known from the delta to the falls of St. Anthony, from Pittsburgh to Cairo and far up the Missouri beyond St. Joe and Omaha.

But the high life wasn’t without its headaches.

Illustration of Howard and Henry
Howard used Henry’s illiteracy to his advantage by trying to steal her fortune.  Illustration by Kenny Wroten

The price of success

As a prosperous den mother, Henry ran into her share of challenges. As she became more and more famous, the press often trashed her enterprise and condemned her character. The Post-Dispatch claimed Henry “surrounded herself with both colored and white inmates, and the place became the rendezvous of the reckless and lawless,” adding, “The nights were given over to drunkenness, ribaldry and debauchery, and no form of sin was too sickening to find harbor under her roof.”

Henry’s greatest competition came in the form of a lively biracial newcomer whose presence and tenacity completely blindsided her. Sarah “Babe” Connor, also formerly enslaved, quickly established herself as a rising star among brothel owners in St. Louis. Connor had much that gave her a competitive edge over Henry: She was almost 40 years younger than Henry, and her fine hair texture and lighter complexion aligned more with European beauty standards.

As Howard had with Henry, a man named William Mara became close to the younger madam. Mara had once sponsored another brothel queen, the late Eliza Haycraft, and he took an interest in Connor, helping her move up the ranks in the bawd world.

To Henry’s horror, Connor suddenly one-upped her by opening her own pleasure house (which she called “the Castle”) just a few doors down, with Mara’s help. She painted it stark white and paraded her night workers by having them dance in the window. The establishment, according to the University of Missouri-St. Louis’s Virtual City Project, “was a high-class venue with luxurious rugs, tapestries and artwork … [and] was also the hangout of many of their pimps, whose fine suits and diamond jewelry made them equally elegant. Men murmured in code as they smoked their after-dinner cigars: ‘Are you storming the castle tonight?’”

Yet her fierce rivalry with Connor wasn’t Henry’s ultimate undoing—that came via a betrayal even closer to home.

Poison pill

Henry reigned for nearly three decades as St. Louis’ renowned bordello empress, but she concealed a wretched secret: She was illiterate.

An illustration of Madam Priscilla Henry
Madam Priscilla Henry Illustration by Rori! / Courtesy of Missouri Historical Society Press

No one taught her how to read or write after she fled the misery of one of Alabama’s biggest plantations and trekked north in search of better days. Howard used Henry’s ignorance to his advantage—by trying to steal her fortune. At one point, he coerced Henry’s longtime chef, Florence Williams, into impersonating the madam on a visit to a notary and tried to secure a fraudulent deed to Henry’s establishments.

But Henry had a hunch.

In the early days of building her sex trade empire, Henry decided it was in her best interest to secretly hold on to a portion of the monies traded by her working girls’ clients for sex. Years of accumulating wealth Henry out of Howard’s reach eventually allowed her to make her most substantial purchase: the Forks of Cypress plantation in Alabama, where she was born and raised enslaved.

Henry’s investment was monumental: In an age when Black women were still dismissed as second-class citizens unworthy of basic human decency, buying the very plantation on which she was raised was an unheard-of success story. (Sources differ on whether Henry bought the entire plantation or only the part on which members of her family lived.) She also moved her sister Nancy Leathe and her six nieces to St. Louis and bought them their own property. As one more act of cementing her independence, Henry ultimately left most of her estate in her will not to Howard but to Leathe.

Furious at this turn of events, Howard allegedly turned to drastic measures. The Henry family alleged that Howard poisoned Leathe, who died shortly after—then poisoned Henry, too. Over the course of a few months, she grew sick and became unable to care for herself. Perhaps Howard had access to her cook and slipped poison into her meals. Or he may have known if she was taking medication and hidden toxic pills in the mix.

Illustration of Tom Howard holding a bottle of poison
Henry and her family accused Howard of stealing from her before progressing to murder.  Illustration by Kenny Wroten

In court, Henry and her family accused Howard of committing heinous acts against her, starting with theft and progressing to murder. The St. Louis Globe-Democrat reported in August 1895:

Priscilla Henry, colored, keeper of a disreputable place on South Sixth Street, has asked the police to arrest Thomas R. Howard, a white man, who has been making her house his headquarters. The woman claims that on June 28, she gave Howard a check for $215 to pay the funeral expenses of her sister, and that on July 2, she gave him $50 to pay rent for the house. Each of these Howard converted to his own use.

Howard was later arrested, and Leathe’s daughter Ida Leathe testified against him, claiming he was slowly trying to poison the whole family in hopes of becoming heir to Henry’s estate. Howard denied the claims, but his defense was less than convincing.

“I have been drunk for a month,” he said, according to the Globe-Democrat, “and don’t remember what happened. Besides, I have been shot through the head, and my brain is often disordered.”

As Howard awaited trial, Henry eventually succumbed to illness. A coroner checked for traces of opium and morphine in the brothel owner’s system, but conclusive findings were never reported.

The case against Howard was dropped, and he never served jail time. In 1899, his body was discovered in the Mississippi River, not far from where he and Henry first met. There were many rumors and guesses, but the truth of how Howard met his fate was lost to history.

After Henry’s death, her surviving nieces inherited her fortune and allegedly faded into obscurity after running through her funds.

The ruins of a building destroyed by the Great Cyclone of 1896
The ruins of a building destroyed by the Great Cyclone of 1896 Public domain via Wikimedia Commons

Little else is known about Henry’s legacy. The catastrophic Great Cyclone of 1896 ransacked St. Louis, claiming over 200 lives and destroying many buildings, likely including Henry’s extravagant brothels. Today, the area is home to several abandoned warehouses, office buildings, tech startups and co-working spaces. These downtown streets will forever hold the stories of Henry’s complicated life and overlooked greatness—a Black woman determined to win, regardless of her struggle; an illiterate, formerly enslaved entrepreneur who rose to become a bordello queen.

Lyndsey Ellis is a writer and teaching artist who is passionate about exploring regional history and intergenerational experiences in the Midwest. Her work appears in Shondaland, Kweli Journal, Catapult, the Rumpus, Literary Hub and Electric Literature. Ellis’ debut novel, Bone Broth, was published by Hidden Timber Books in 2021.

This article is republished from Narratively, a storytelling platform that celebrates the diversity of humanity. Read the original article.

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