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Anna Wilson, died Oct. 27, 1911, aged 76 years and 5 months, according to the inscription at Prospect Hill Cemetery in North Omaha. This plain message gives no hint that Wilson was quite possibly the most successful businesswoman in the history of early Omaha. It could be said she was in the human relations industry. More to the point, she ran the most lucrative prostitution ring in the freewheeling, rowdy and often violent days and nights of the young railroad town. She hosted notorious all-night balls, loved champagne and fine jewels and wasn't afraid to assail a rival businesswoman if need be. Such behavior earned her the moniker "Queen of the Underworld." But that was only one facet of her personality. By all accounts, Wilson treated her girls with respect and attention. She provided medical care and financial support when they no longer could earn money in her houses. She guided many to respectable lives, and in her final years, she attained respectability herself. So, to many contemporaries, she also was known as the "Soiled Dove with a Heart of Gold." Through her human relations business, coupled with shrewd real estate investments, she amassed a fortune that reportedly ranged from $250,000 to $1 million. And she gave almost all of it to charities in the city she loved. And that is why she is sometimes referred to as "Omaha's Most Magnanimous Madam." Her kindness and generosity haven't been forgotten. On Memorial Day, some 300 people will gather at one of the state's oldest cemeteries to pay tribute to deceased veterans, state senators, community leaders and influential pioneers whose names now appear on Omaha street signs, schools and even a county or two in Nebraska. After an invocation, a rifle salute and a rendition of "Taps," people will file over to the granite slab. A respected member of the ensemble will read the "Eulogy of a Soiled Dove" and a band will play Dixieland jazz. Then, as has been done on many Memorial Days, someone will place a yellow rose on her grave. "We have more fun with Annie being here than the so-called upright and moral people," said Louise Baumann, a longtime member of the Prospect Hill Cemetery Historical Site Development Foundation. But who was Anna Wilson? What is known of her past? And why didn't she leave her fortune to relatives? While the answers to such questions prove elusive, they also provide a fascinating glimpse into the state's early history. Emmett Hoctor of Plattsmouth, a Wild West historian who dubbed Wilson the Magnanimous Madam in a 1997 article for a national genealogical newsletter, said she "wanted to remain a woman of mystery." For source material, he relied on "The Underworld Sewer" by Josie Washburn, who worked for 20 years in Nebraska's houses of prostitution, including Wilson's. Hoctor also combed the microfilm libraries of early Omaha newspapers.
The most prevalent explanation of her past was that she was born in 1835 to a good family in Georgia. Some say she was the daughter of a Baptist minister. "I think she got herself compromised," Hoctor said. "And once that happened in that generation, you had two choices: Commit suicide or become a prostitute. You were ruined." Wilson apparently spoke little of the matter, but she once told friends late in her life that she had returned to Baton Rouge, La., in an attempt to reunite with her family. The attempt was rebuffed. Around 1866, she came to Omaha, then a railroad boomtown where gambling, drinking and shoot-outs were rampant. She took a job with a riverboat gambler and saloon owner named Dan Allen. A romantic relationship blossomed. Wilson must have quickly demonstrated her business acumen, because she soon took charge of a series of "houses that weren't homes." While some of her outlets undoubtedly serviced railroad workers and cowpunchers, she also managed a palatial, 26-room house in the downtown district worth $100,000. The establishment was near the Territorial Legislature, and many believe it was frequented by powerful lawmakers and business leaders, Hoctor said. Downtown excavations in subsequent renewal projects revealed a network of tunnels linking taverns and cigar stores with the Wilson mansion. "Workers have found ... well-trod paths where secretive clients could discretely visit the 'tenderloin' district by torchlight," Hoctor wrote in his article. In the 1800s, prostitution was a quasi-legal business in many western states and territories, Hoctor said. Judges, some of whom were likely bribed, often looked the other way as long as the houses paid regular "fines" to their municipalities. Wilson's very public lifestyle provided great fodder for Omaha newspapers. An account from 1869 described a "disgraceful fracas between a party of women connected with rival establishments," in which the prostitutes duked it out in the streets. Or at least, in the words of the unnamed reporter, they "indulged in several rounds of pulling hair and scratching faces. Ball dresses were torn to tatters." Another story in 1875 told of Wilson -- who had passed out from too much champagne at one of her own balls -- having been liberated of $10,000 in jewels. Local law enforcement officers willingly came to her aid, collared the suspect and saw that he was sent to prison. In 1884, her confidant, lover and business partner, Dan Allen, died from kidney disease. In subsequent years, Wilson made a transition to the real estate business, where some estimate she made half or more of her fortune. Hoctor said she also lived a contemplative life, seeking salvation in the Bible and reading from her handsome volumes of Shakespeare. Despite her means and respectability, she never forgot those who peopled her former underworld. She was generous with her former employees and to the poor in general. Upon her death in 1911, she was buried next to Allen. She left her estate to the Prospect Hill Cemetery Association, the Omaha City Mission, The Creche (a child protective home), the Child's Savings Institute and the Associated Church. She also gave grants to Bishop Clarkson Hospital and Wise Hospital.
Finally, she gave her downtown mansion to the city of Omaha, conditional to it being run as a hospital. "That's how the city of Omaha came to own the biggest whorehouse in Nebraska," Hoctor said. The city accepted the gift and kept its end of the bargain, using the house as a venereal disease clinic. Eventually the building, along with the entire red-light district in which it stood, was torn down. Wilson's life might have drifted into the ether of the past but for one remarkable event. On Memorial Day, 1912, Mrs. Thomas Kimball, founder of The Creche, laid a yellow rose on Wilson's grave. The mother of well-known Omaha architect Thomas Kimball continued the practice until her death in 1930. The architect took over his mother's Memorial Day tradition until he passed away in 1934. Then a woman by the name of Eloise McNichols accepted the duty. For quite a time, the tradition faded, corresponding to a period when the cemetery fell into disrepair. Then in the 1970s, Baumann and others led an effort to restore the cemetery grounds and work for its preservation. In 1979, the group organized a Memorial Day service at the cemetery. At the conclusion of the main events, several cemetery aficionados said a few words over Wilson's grave and laid a yellow rose on the granite. At first the rose-laying ceremonies were short and discrete because the group didn't want to tempt the ire of those easily offended by Wilson's former profession. But after a few years the tribute became a highlight of the event. Perhaps people can identify with Wilson's story of struggle and redemption. Maybe they like her example of generosity. It might just be they like to hear Dixieland ringing through the trees on a hill in North Omaha. Larry McNichols, president of the Prospect Hill Cemetery board, said it's a salute to just one of the many colorful characters buried in the graveyard. He's the son of the late Eloise McNichols, the last known keeper of the Wilson tribute. So, was he the one who rekindled the tradition? "It's kind of like Anna's background," he said. "We really don't know."
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