Who Was Annie Wynn? Part 1

Anne Wynn was born in 1863 or 1865 (depending on the census response) in Illinois. According to early records and accounts she was one of 18 children and left with a friend on a stage coach headed west in 1880 when she was 17.  Either as an eloping bride or a runaway daughter, she ended up in the mining camps of Colorado. Some claim she married a man named Wynn there in Colorado and others suggest she might be the mysterious Anne Ferguson who bought out a madam in Denver.  Whichever was the case, she worked about seven years managing a “house” or brothel in Leadville before the 1889 Oklahoma Land Run called. 

It is known that in the late 1880’s life in the Colorado regions began to get a little less welcoming for establishments of the type Annie knew.  Businesses such as houses of prostitution, gambling dens, and saloons were being pushed out of sight through laws, fines, and social pressures. The mines were making people money and that brought in civilization and society standards began to elevate to the point that people could begin to pretend they did not use the businesses along the lanes and roads labeled the “red light” districts. Every community had several women such as Jennie Rogers who was 6 ft. tall, Rubensque and said to have blackmailed her way to fame against her major competitor, Mattie Silks.  She built a brothel in 1889 in Denver that had, it is said, tunnels leading directly to the state Capitol!  So there was plenty of inspiration for Annie as she headed to Oklahoma Territory.


Laws, environment, and business, however, all began to change.  In addition, some of the long standing leaders of the houses began to die off or move away.  Like so many others in the era, loading up savings, grabbing a few friends to staff a new establishment, she set off to find her fortune somewhere else.

It is often assumed that claiming land in the run required a male of legal age, so some source writers assume that she had some male with her and there is a suggestion she might have come with a husband. Any single woman of legal age, married women and widows could also make the run in hopes of staking a claim. There was even a special caveat for a widow and some discrepancies for town lots as opposed to section lands that might have allowed her, and othr women, to acquire city lots with the same ease as a farm.  What is known is that she came in on the afternoon train from the south, arriving about 3 p.m. and she saw right across from the crude Santa Fe depot the perfect spot for her to start her empire.  North and south looking west from the wooden platform of the rail depot was a wide wexpanse of dirt soon to become known as “Front Street”.   Already in place, its faro wheel buzzing in the tent covered space to the south was “Kid” Bannister’s Faro Bank. He proudly displayed a sign informing one and all that his establishment was the first “bank” in the new town.  There was a space and then another crude tent was flapping in the warm dust filled April air.  “John Burgess’s Joint” was readying to offer something to wet the whistle after a busy day of racing, fighting, claiming and more fighting. 

The area would win the label “Hell’s Half Acre” for the number of saloons, brothels, and gambleing dens crammed into a small area. Hell’s Half Acre was bounded, primarily, by Front Street (East), Grand (subsectioned into an area called ‘Bunco Alley’ for obvious reasons and now called Sheridan (North), California, with its ‘Alabaster Row’ (South) and Broadway (West).  It spilled over into just beyond the tracks to the East to the domain of the African American Madame, Old Zull aka Martha Fleming.  Town limits were the tracks so she operated just over the tracks and out of some police jurisdictions most of the time. In present Brick town was the Military Reserve Camp where , at the time of the run, members of the 2^nd Co. Infantry and Calvary elements from the 5^th and 10^th groups under Captain Stiles stood ready to assist in keeping the peace in the huge and bustling mass of people.

Big it was!  Estimates were that anywhere from 10,000 to 20,000 people were jostling, jockinging and   jibbing as they tried to claim a lot of land.   Annie eyed that space between two such fine and upstanding businesses as perfect for her establishment.  She would have potential customers passing from both directions every hour of the day and night. Add to that its proximity to the train and nothing could be better.  There is no good clues as to how soon she went into business, but from a photograph of the area within a week or ten days and there is a distinct third tent in place between those two other establishments.

Big too were some of the women filling these roles as courtesans, soiled doves, prostitutes, whores, and other terms used to describe women who worked in the sex trade of the 1800’s and early 1900’s.   She was called “Big Annie” because physical descriptions of her indicate she weighed about 200 pounds and may have been tall as well.  This was not unusual in her profession; indeed, in Leadville and Colorado, many of the most prominent soiled doves were larger women of a decidedly tall or Rubenesque physique.  Photos from one house shows the range of women working there and most are 6 feet and larger in form.  Annie was not alone in this label in Oklahoma City.  “Big Liz”, aka Mary Belle Everhardt, was said to tip the scale at nearly 400 pounds.

At some point she developed a partnership with her opposite in the African-American community, “Big Zulu.”  Together they apparently promoted some specific political activities, offices, and individuals who no doubt helped protect their own assets and operations.  She may have kept notes and names in order to protect herself and her girls in the event local police, politicians, community people, business leaders, or even the U.S. Marshalls became too moralistic.  This might explain how that in nearly 20 years of operation she never appeared to suffer any great restrictions or punishment for illegal activities until just before she left town as the community began to change in major ways.

In the 1890's her name appears in several early newspapers and most of it was, surprisingly, related to real estate deals.  In April of 1896 she and another woman, Kitty Nelson, were found guilty of keeping bawdy houses. It was noted the sentences were 30 days in jail or a fine of not more than $500.  It was not clear if the two women were being charged for the same bawdy house or represented two different establishments. In August of 1896 she and C.G. Frost faced off at a Sheriff's Sale concerning city lots #20,21,22,29, 30 in Block 64, Oklahoma City.  In late February of 1901 S.R. Cook sold Lots # 29, 30, Block 64 for $200 to Annie. It appears some of her notoriety may have stemmed from , not so much from the bawdy houses and beer pavilions she ran but on her daring to step into the business of buying real estate like the other wheeler-dealers in the new community.

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

To be continued.
[Author Hudson, who is also a storyteller, is working on a solo performance highlighting this woman's fascinating life]