Undercover in a Man’s World: The Strange True Story of the Milwaukee Women Who Lived and Worked as Men

For women a century ago, dressing as a man could better your job opportunities… and land you in jail!!

In the late 19th century, it was a crime to walk the streets dressed as a member of the opposite sex. Beat cops on patrol would notice an unusual individual and stop to question them to determine if they were up to no good. 

This was the case with a woman caught standing with another woman outside a downtown theater on an evening in January 1897. Mrs. John Peterson was dressed in a stylish man’s suit and blue overcoat with a new brown fedora. Completing the masquerade, she wore a fake mustache and wig. While she and her friend were waiting to meet another friend outside the Alhambra Theater at Fourth and Wisconsin [then Grand Avenue], a police officer stopped and asked them about their business. The masquerade was discovered as soon as she answered – unable to disguise her voice, Peterson was arrested and fined $10 for disorderly conduct. 

Wicked Milwaukee by Yance Marti


Yance Marti is an engineer for the city of Milwaukee’s Department of Public Works who researches and writes about Milwaukee history in his spare time. This story is an excerpt from his latest book, Wicked Milwaukee (The History Press, $24), detailing sordid (at least for the time) aspects of early life in the Cream City, with chapters on the red light district, speakeasies, communists, opium dens and more.

Living an undercover life was risky, but in many cases the risks were worth the freedoms and economic benefits. Many of the women whose stories follow were able to support themselves living as men when women generally were paid a fraction of the salary of men for more difficult work. It was also worth the risk to be true to a person’s gender identity.

One of the earliest instances reported locally was the following article from the Milwaukee Sentinel of Monday, Aug. 24, 1863: 


On Saturday a girl giving her name as Frank Scott, was arrested on the street, dressed in man’s clothes and taken to the station house. The police received information several days since that a girl so disguised was traveling through the state. Policeman Chas. Cunningham has been on the lookout for her for the past two or three days. She passed him on Friday, but she was so well disguised that her appearance only aroused his suspicions. He watched her, however, and on Saturday arrested her, and found that his suspicions were correct. She has been parading several days without detection. She was so well disguised that she met her own brother and enquired about her family, and he never discovered that he was talking to his sister. Why she would thus unsex herself remains a mystery. [/alert]

The one odd word in this article that stands out is “unsex.” The newspaper used the word to refer to women or men who denied the specific gender role of their sex. Men had distinct roles; they could vote, provide for their family and dress only in male clothing. A woman attempting any of these acts was unsexing herself. Any deviation from that role in behavior or dress would be considered an actual crime. Well-known Wisconsin poet Berton Braley summed up the absurdity in his poem “Unsexed,” published in the Waukesha Freeman on Feb. 26, 1914:

[alert type=white ]It doesn’t unsex her to toil in a factory

Minding the looms from the dawn till the night;

To deal with a schoolful of children

Doesn’t unsex her in anyone’s sight.

Work in a store – where her back aches inhumanely –

Doesn’t unsex her at all, you will note,

But think how exceedingly rough and unwomanly

Woman would be if she happened to vote.[/alert]

A SENSATIONAL CASE that ended up making headlines for several days in 1899 was that of Harry Hynes, also known as Harriet Brown. At the Alhambra Theater on the evening of Aug. 29, 1899, the famous national touring act of Ward and Vokes performed an evening of musical farce. The spectacular mix of comedy, dancing, skits and other acts drew rave reviews from around the country. A police officer watching the patrons exit after the show noticed something odd about a woman waiting outside the theater. The police officer approached her and tugged her hair to discover that it was a wig. As with any person acting suspiciously, she was taken to the police station for further investigation. 

As mentioned in an inter view after she was caught, as a man she “had greater liberty and much more pleasure.”

It wasn’t until she was being booked for disorderly conduct at the central police station that the complete truth of Harriet Brown was, quite literally, uncovered. Harriet was discovered to actually be Harry when a matron at the station began frisking him. At the matron’s first touch, Harry told the police that she was a he. The police questioned him thoroughly and investigated his room at 816 W. St. Paul Ave. They searched his suitcases and found men’s and women’s clothing, along with letters and a few books.

The story eventually pieced together about Harry was that he was from Edgerton, Wisconsin, where he had lived with his mother. She had died in 1897; afterward, he began to more freely dress as a woman, leaving the hometown for Madison, Milwaukee, Chicago and other cities. He worked where he could in vaudeville music houses, trying to become a professional female impersonator, perfecting his mannerisms, high-pitched voice and wardrobe. He had arrived in Milwaukee about a week prior to the arrest but was only able to find work as a female domestic. It was likely that Harry went to the theater performance hoping to be hired for the traveling show. During the short court appearance the day after his arrest, he was sentenced to pay $15 and costs or serve 60 days at the Milwaukee County House of Correction. Unable to pay the fine, he served his sentence, forced to dress as a man while laboring to cane chairs in the prison woodworking shop.

Illustration by Jason Frederick

THE EARLY DECADES of the 20th century was a time of the women’s suffrage movement, in which women were mobilized by the work of activists like Emmeline Pankhurst to fight for their rights. Pankhurst was the leader of the militant suffragette movement in England and had come to the United States on a speaking tour in the fall of 1913. During the tour, she gave her most famous speech, “Freedom or Death,” in Hartford, Connecticut. The principle of the fight was the idea that women should have the same rights as men, should be able to work jobs that afforded them the ability to support themselves, should have the same political power as men. The speaking tour was widely reported across the country and doubtless had a large influence on many young, disenfranchised women. It inspired women across the country to free themselves from a male-dominated society that would otherwise force them into accepting minor social roles or, at worst, into the underground economy of vice.

One of the more well-known accounts of living as a member of the opposite sex took place in 1914. In that year, Cora Anderson had been living a successful double life for nearly 10 years as the dark-skinned South American Ralph Kerwineo. Before her male transformation, she had been studying nursing in Chicago at the Provident Hospital Nursing School. In her class, she became good friends with Mamie White, also of mixed race. After their graduation in 1900, unable to find employment as nurses in Chicago, they lived together trying to make a living working various jobs. They left for Cleveland, hoping for better conditions, but weren’t entirely successful. It was about that time that Anderson began toying with the idea of dressing as a man to find better opportunities.

In Cleveland in 1904, Cora had made a pact with Mamie to act as a married couple, with Cora in the part of Ralph Kerwineo, the husband. They came to Milwaukee in 1906, settling into their new roles. Ralph was able to work at jobs that afforded a higher salary and provided better work opportunities than she could find as a woman. Combining their salaries allowed them to enjoy a higher standard of living. In 1910, Ralph found a job working at Cutler-Hammer Mfg. Co., making a good deal more than she had seven years earlier as a nurse in Chicago. One of the other benefits she found was freedom from the advances of male “mashers” making unwelcome sexual advances. It was a problem in every big city, making it uncomfortable for women to walk the streets without an escort.

Cora and Mamie managed to live happily in this arrangement until, slowly, Ralph began to take on more traits of the “sporting man” of the era. Ralph started hanging out at pool halls and dance halls. He took up the cigarette habit. He became an expert fanatic of all things baseball. As mentioned in an interview after she was caught, as a man she “had greater liberty and much more pleasure.” The search for pleasure as a young “sport” led to flirting with women she met in the dance halls. It was late in 1913 when Ralph met 21-year-old Dorothy Kleinowsky while out on the town. They fell in love shortly after. By this time, Ralph’s independent manlike behavior pulled him away from his relationship with Mamie, and they moved out of each other’s lives.

The love affair that grew out of the meeting between Ralph and Dorothy resulted in their marriage in March 1914. The newspaper articles did not state if Dorothy knew Ralph’s true gender or if it didn’t matter to her. After their marriage it would have been difficult to hide. The eugenic marriage laws of the time required a doctor’s certificate to prove that the husband was fit for marriage but rarely required a physical examination. The laws were supposed to prevent unorthodox marriages, especially marriages between women. It was relatively easy for Ralph to procure the certificate from a doctor who took it for granted that he was a man. 

Meanwhile, Mamie found out about the marriage and grew angry. Heartbroken, she went to the police with the story of Ralph’s double life. It didn’t take the police long to investigate this strange confession, and Ralph Kerwineo was arrested at the Cutler-Hammer plant on May 2, 1914. Newspaper reporters at that time were always on hand at the central police station looking for news, and as soon as Ralph was brought to the jail, stories were being written for the next issue of the dailies in the city.

Had the case been reversed, and had it been a man posing as a woman, it would have been far more serious.

In jail, the full story of Cora Anderson was revealed by interviews with her and Mamie White. Cora was the daughter of an African-American man and Native American woman from Indiana. She was forced by the district attorney to return to dressing as a woman in time for her court appearance on May 5. The court handed down a decision of guilty of disorderly conduct with a suspended sentence. Judge Page made a mysterious comment during sentencing: “Had the case been reversed, and had it been a man posing as a woman, it would have been far more serious.”

Immediately after she was released, Cora was offered an engagement to perform on the vaudeville stage, where she told the story of her life as a “Man-Woman.” She began the circuit at the Orpheum Theater, telling of the stages in her life and changing costumes to portray herself during those stages. The popularity of the performance and her natural ability to tell her story led to offers around the state from other theaters. In the same issue of the Milwaukee Daily News telling of these vaudeville offers was a small blurb describing another performance: “Tall Blonde is a Man – A tall, handsome blonde sings several songs in the ‘Liberty Girls’ show at the Gayety before audiences learn that the singer is a man. The clever female impersonator is Gene Gomez.” It appeared that these shows were becoming common and that, at least on the stage, impersonators were acceptable. 

IN JULY 1915, a few other young women were discovered living as men. Jessie McNeil was a well-educated young girl who seemed to pick up on many of the teachings of the suffragettes. She was brought up in a poor, conservative farming family near West Allis, one of eight children, four boys and four girls. According to a newspaper account, when Jessie was born, her mother had hoped for a boy. When she finally turned 18 and left home to live on her own, she decided to become the man her mother had wanted. As a woman, she was able to find factory work paying $4 per week. Shortly after she started to wear men’s clothes and cut her hair, she was making $10-$14 a week in restaurants in Chicago – enough to pay her rent and help her mother with the bills. 

Early in 1915, Jessie moved back to Milwaukee into an apartment at 726 W. Winnebago St., sharing it with Emma Jacobs, a 33-year-old African American woman she had met while working at a restaurant on Grand Avenue. So as not to arouse suspicions with the landlady and neighbors, Jessie and Emma posed as a married couple. Unfortunately, a Hungarian boarder living in the same building became suspicious and notified the police. Police detectives caught up with Jessie on the evening of June 30 at the corner of Fourth and Juneau. When confronted, she admitted that she was a woman. Detectives took her to the police station, where she was arrested for vagrancy. Jessie was held in jail from July 1 through July 8, until a court hearing could be arranged. During that time, she was interviewed by many news reporters who detailed her story, including thoughts about the difficulties of young women surviving in a world dominated by men.

At the time Jessie was arrested, a young woman named Dorothy McCoy from Montfort, Wisconsin, was taken into custody by the police. She was reported as Milwaukee’s third “man-girl.” After graduating from high school, she left Montfort to escape the pressures from boys in the suffocating atmosphere of the small town. She told her parents that she had a job offer in Chicago and took a train to Janesville. She bought a man’s suit and trimmed her hair in the style of a man, hoping that she could escape unwanted attentions from men by masquerading as a man. Trying to decide on her future, she departed to Madison, then to Chicago and finally to Milwaukee. After a few hours in Milwaukee, she was hoping to catch a train to Madison but missed it.

While waiting at the Chicago and North Western station on the night of July 2, she was picked up by detectives who noticed that she wasn’t “walking like a man.” The police contacted her family, and her father telegraphed back asking for her return home. Among her possessions when she was arrested was a Bible with several passages marked, including Psalms 17:15 – “As for me, I will behold thy face in righteousness: I shall be satisfied, when I awake, with thy likeness.”

Times and fashions were changing. Short hairstyles for women were hallmarks of the Jazz Age, and the slim, boyish look for women was in vogue. In 1920, women were granted the right to vote. Arrests of women dressed as men seemed to drop off the radar, with cases few and far between. Still, vice officers made discoveries of others living double lives.

In September 1932, there was the case of a raid on a “hobo camp” on the West Side. A womanish man was one of those rounded up and was found to be 33-year-old Martha Frances McDonald dressed in overalls and with a “boyish haircut.” She was sentenced to 30 days in the House of Correction for vagrancy.

And appearing in the newspapers on Nov. 4, 1939, was the case of Mildred “Tommy” Allen. The previous night, a car driving on the North Side was stopped for a missing license plate. The officer took the two men in the car into custody. The driver was 17-year-old James Mercurio; the other gave the name of Tommy Allen. When questioned at the station, an officer noticing the soft features of her face stated, “You’re a woman.” She admitted that she was, surprising her companion.

Illustration by Jason Frederick

Mildred then told of working for a construction company in Rock Falls, Illinois, seven years earlier as a timekeeper. Her boss half-jokingly suggested that if she wore men’s clothes he would make her a construction superintendent. She came back the next day wearing men’s clothes with short hair; without another word, she was given a promotion and a raise. The following year, her husband died. As a single parent needing to take care of her young child, Mildred continued with the charade.

Similar to Cora Anderson’s story, Mildred ended up getting married to a woman in 1937, and they continued living in Rock Falls. Mildred had been in Milwaukee for only a few days to visit relatives when she was caught. At district court on Nov. 8, the judge ordered her to leave town or face a 90-day vagrancy sentence. She complied by leaving the city.

Several years later, in January 1943, she was arrested in Chicago without a formal charge. The news piece said she had posed as a man for 15 years and was carrying a draft card bearing the name of Thomas Vernon. Under this alias, she was working as a photographer of children. In a strange twist to the case, she was posing as the husband of Esther Hoffman from Indiana. To lend more credibility to their “marriage,” they had acquired a baby on an installment plan for $2 down.

“Undercover in a Man’s World” appears in the March 2019 issue of Milwaukee Magazine.

Find it on newsstands beginning Feb. 25, or buy a copy at milwaukeemag.com/shop.

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