Who Was Anne Wynn Bailey? Part 2

ca 1908
When the 1900 census came along she was ensconced in her establishment at 422 West 2nd, a step up from the street of “Hell” and a sign of how economically successful her business, and others like hers, were in those early days.  Apparently Anne acquired many types of coin as she grew her empire: money, real estate and possibly information.  When the census taker asked, she, and all of her girls, appear to have very proudly claimed the occupation of “Prostitute.”  In many other locations euphemisms were often employed but not so in Oklahoma City and "Hell's occupants.

The house was only one of the businesses she oversaw in the city, only part of the real estate she owned.  It has been suggested she served as a 'silent partner' in other, and more legitimate, businesses but evidence is lacking to date.  She was, despite the vindictive of local news reports and inconsistent police and community leaders,  a fashionable woman who could mingle unnoticed among the finer shoppers of any of the stores or shops targeting higher class women. It has been reported that her patronage was welcomed in shops and offices all up and down the bustling and growing urban center.
She was, unlike many of the women in similar business, particularly hated and reviled.  Indeed, seldom is another Madam named as often, and never with as many derogatory remarks, as is “Big Annie”.   That includes fairly recent writers of early day accounts. The myths that grew around her were apparently crafted to achieve specific goals and may have stemmed from professional jealousy and competition from other Madams, from real estate speculators she out maneuvered for valuable locations or buildings, and for local politicians (which often included local police and community leaders) seeking to use her as a scapegoat to climb to positions of power themselves.

In the 1902 Oklahoma City Directory she is listed as "Miss Annie Baily" and was residing at 422 West 2nd. Locals would understand this was in "Harlot's Lane" as both sides of West 2nd (now known as Kerr) from Hudson Street to Walker Street was primarily occupied by the major and miner houses of prostitution.  These included on the north side of the street: Etta Woods Creole Girls, The Red Star, Noah's Ark,. On the south side were: Nine Truelove's, The Arlington (co-owned by Annie and managed by Madam McDonald), and at the corner of W. 2nd and Walker was "Big Anne's Place 444" managed by Madam Effie Fisher.  It is believed she still owner property in Hell's Half Acre and across the railroad tracks east into "Old Zulu's" domain as well as other business property.

The tide of her life in Oklahoma City was not as smooth as many liked to claim. This was especially true in 1903.  In February a young Dutch girl, Lucy Platt or Patt (her name appears both ways but in legal records the Patt appears most often) who sued for $20,000 in damages against Annie Wynn for her being drugged and raped in the W. 2nd business.  Her uncle was mentioned as a key player in luring the girls into the bar and allowing the girls to be drugged and assaulted. A shiver of fear of "white slavery" was always under the surface in this era and so the story was followed in a most salacious and outraged manner.

Two men, George C. Garrison and John Harmon would be implicated, with Garrison being sent to Lansing for 10 years.  In June, Annie Wynn and Maud Davis were fined for contempt in relation to the case. This was just days after Annie had married a local land speculator named Asher Bailey. Subsequent legal records indicate that other witnesses noted that the girls did not refuse entry into the saloon, the drinks or the journey upstairs and neither one called out for help. Two noted the girls came down with the men later. The girls appear to have disappeared as suddenly as they appeared.

In November, local headlines informed the public "Sporting Woman Killed" and it was learned that local Madam, Effie Fisher was shot through the window of her house at 444 W. 2nd,  by a double-barreled shotgun. She was killed instantly and the employee, Sadie, with her at the time was sprayed by stray shot but not seriously hurt.  The initial theory was that Effie was rich, she had days earlier filed a will and let it be known that if anything happened to her look to her ex Ed Filson.  The truth was she had very little beyond the house she owned and the house she managed, some bits of furniture and not enough to give support to her aged father or anyone else.  Filson was acquitted. 

!903 seemed to be a very bad year for Annie Wynn.  The Patt girls incident had all the appearances of a set-up perhaps to get Annie closed down and sent away?  Annie marries; was this to protect her interests or because a  husband or wife could not be compelled in that time to testify against their spouse?  Then, most strangely, the busy year concludes with the killing,  unsolved, of the woman who had risen to the place of managing Annie's most popular business at 444 W. 2nd?  Had Effie been involved in a plot to take down her boss? Did she see herself filling Big Annie's shoes and assuming control of her empire?

Statehood was all the talk in 1907. The territories would become a state and everything would change.  In June a mysterious and shocking murder rocks Capital Hill and Oklahoma City. James Meadows disappears and then in a scene Hollywood would envy, the young German immigrant lover of the man's wife, leads police by lantern light to the grave site as lightening spears the stormy skies.

The next year and a half the newspapers were the equivalent of the television soaps of modern decades.  There were tales of mystery women, psychics, mysterious letters, false confessions and denials and accusations on a daily basis. The frail put upon widow, the eager tormented and easily led lover, and the poor sap of a husband done in by...one of them? Both of them? Neither of them?  tales have emerged of the wife's affair with a local high profile police officer adding even more drama and conspiracy to events. As if it needed more. The wife, apparently was addicted to morphine and may have led a colorful life before marrying Meadows.  Meadows was the put upon husband but there are many unanswered questions about this man who worked for the telegraph and phone company. A suggestion is he was a gambler and still had some connections.  The young German, besotted and manipulated, had been married before and his wife tragically (Mysteriously?) died after an outing to the country.  Who to believe?  Finally, the courts believed the young man had killed Meadows, but many felt he had been tricked into it by others.  He was sent to prison in McAlister but later released and is believed to have moved to the area of Osage County.

All of this was heating up the already steaming days of June and July of 1907 when in August a fire of different sort heated things up.  A conflagration broke out at 312 E. Grand, one of Annie's other "resorts". One man and three women, unnamed, were killed as the building burned to the ground. Annie, and the black porter of the business, "Judge Peters" were arrested for arson and murder. Police believed a story of Fannie Richards, a one time employee of Annie's that she had killed a man and dumped his body in the North Canadian and then order Peters to burn the house down to conceal the crime. As a result Annie was forbidden to go back to West 2nd street and had to take up residence elsewhere on E. Grand. She was, after nearly 20 years, almost back where she started from.

Statehood celebrations and changes marched onward. Old Zulu, Martha Fleming, the night before statehood attended a revival in the old and very notorious Blue Front Saloon.  A holiness group was using the defunct and rundown building to conduct services. She was converted and the next day, in the November chill, she was baptized in the local river.  She had battled for many years the twin demons of drugs and drink.  Her notoriety was not for business sense or management skills or social activism as she drummed up voters for election days but was the fact this 6 foot woman was an Amazon when under the influence. On one occasion it took nine large police men to restrain her and get her into the cell. Unfortunately, her conversion was short lived and not much more is known other than she may have been returned to jail in Kansas after this date.

Statehood was not all celebration, however, as the entry into the union meant that the state became dry with the stroke of the President's pen.  An estimated 560 legal saloons closed across the region of the territories and 70 of them were in Oklahoma City.

The brewing discontent and revilement of the Madam Annie Wynn reared to new life in 1908 as the woman who had found so many fines and bails paid by patrons now faced jail time. On May 19 she went on trial and the chief witness was that ex-employee Fanny Richards. The holes in the story did not escape the jury (if you have dumped the body why burn down the building? )  The inquest jury did not buy her or her tale of the arson and murder. The jury dismissed the charges and Annie was free.

Possibly Annie had met the jailed widow James Meadows on one of her in and out visits to the jail cell while the arson and murder case was developing. Perhaps she read of her in the local paper and felt sorry for her as a fellow traveler on the bumpy road of public opinion. Whichever was the case, Annie offered Lila Meadows a place to stay on at least one occasion.

Spring of 1909 brought with it great changes. The March city elections forecast "stormy" as one major candidate for the mayoral position was a strong "anti-saloon league" member.  Annie, a part of Oklahoma City's landscape since April 22, 1889, sold out and moved west. The $75,000 she had amassed had apparently been  used to keep her out of jail and away from a death sentence.  She is believed to have moved to California and there within the next decade.

Various records of the early days of the city have painted her with a broad and sometimes vicious stroke while leaving many other women in similar employ alone. One has to wonder why this was the case. In a wild and roaring town like Oklahoma, step-child of a land that had long survived as a hideout and hold for bandits even the good guys played both sides of the fence.  Sometimes, the shrill declarations of woman Annie Wynn are like a glass of wine that carries the haunting taste of sour grapes.  Annie Wynn Bailey may have been an early example that sometimes the smartest man in the room is a woman.

(c) Marilyn A. Hudson, "Who was Annie Wynn?", Mystorical, 2015.

[As more is uncovered I will add it to this. Descendants of any of these people are invited to contact me to expand the information found her. ]
The drawing found  in a 1908 Newspaper in OKC was probably caricature;
her features were drawn with a course, male face, heavy jowls, and rough features. A sure sign of the distain and hatred she generated among the writers of that newspaper. She was reported to have been big but other features are speculation. IF the 1908 image was caricature and not merely a male face on a female figure than it is possible she had a prominent nose and might have looked like this when younger.  Marilyn A. Hudson, 2015.

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