The Legend of Dirty Helen

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When Helen Cromwell (nee Cromell) arrived in Milwaukee, she was 41 years old. Her once-stunning good looks and buxom figure was worn down from “entertaining” at least a thousand men, smoking countless Lucky Strikes and consuming gallons of bourbon and scotch. A sucker for good-looking men and expensive clothes, Helen was a party girl with two sons, six husbands, and myriad gangsters, bootleggers and bank robbers for boyfriends. The significant men in her life either left her or died, some under mysterious circumstances. She hardly ever saw her sons, who were raised by various family members over the years. 

Recently, Great Lakes Distillery honored her with a high-end whiskey that bears her name. Dirty Helen Barrel Strength Whiskey is distilled, aged, and bottled in the Milwaukee using Wisconsin-grown grain and carries a palate of sweet corn, charred oak, roasted malt and vanilla. 

Helen made—and lost—more than a million dollars in 83 years. The onetime sex worker, high-priced call girl, madam, speakeasy operator, restauranteur and saloon proprietor died penniless at a local care facility in 1969. Her famous and infamous friends like Al Capone, Big Jim Colosimo, Gloria Swanson, Liberace, numerous members of the Milwaukee Braves and Senator Joseph McCarthy had all passed on. Her attempts to reconnect with her sons were painful, and ultimately disastrous. After a lifetime of good fortune, Helen’s luck had finally run out.

High-Priced Brothel

Helen Cromell was born in 1896 to an upper-class Indiana family. Just out of high school, she eloped to Ohio and married. Her husband operated several Cincinnati saloons for the local vice lords and often stayed away from home all night long. While pregnant with their second child, Helen learned her husband was involved with the city’s most prominent madam. Helen savagely clawed the woman’s face and breasts before throwing her headfirst down a flight of stairs. With her husband out of the picture, Helen became a sex worker, often receiving $100 or more per customer. Once she learned the business from the inside, Helen became a madam and created a high-priced brothel that catered to wealthy men from out of town.

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The 1920s had just started to roar when Helen operated successful brothels in Cincinnati, San Francisco, Chicago and Superior, Wis. 

But it wasn’t until a chance visit to Milwaukee in 1927 that she put down roots and stayed for the next 40 years. At that time, the neighborhoods south of Downtown housed more than 300 speakeasies and brothels, many of them located in the Mineral Street and National Avenue neighborhoods. On St. Paul Avenue, underneath the present expressway, there were more than two dozen brothels, and Helen impulsively chose a 30 x 65-foot tavern building near 18th Street to open a business. For $300 she leased the property from the Schlitz brewery’s real estate division and hired cleaners, carpenters, plumbers, and painters to transform the down-at-its heels barroom into a saloon and restaurant called the Sunflower Inn.

Larger Than Life

Two weeks later, with her cash reserves exhausted, Helen opened the doors and served remarkably good food and moonshine whiskey. Word of mouth brought customers in by the carload, and within a month, she populated the upstairs rooms with goodtime girls poached from other similar establishments. The Sunflower’s popularity continued to grow, and Helen got rid of the tables and chairs to accommodate more patrons. Because of her larger-than-life personality and friendly insults to the regulars, nobody minded standing or sitting on the floor. 

One evening when she unleashed a string of curse words at the piano player for being too intoxicated to perform, she became a legend. The crowd went wild, and after that, she developed a well-deserved reputation as Dirty Helen, the most entertaining and foul-mouthed saloon owner in the country. Her old friend Al Capone sent a gifted carpenter from Chicago to build a 20-gallon dispenser concealed in the wall. In all her years of running the Sunflower, no policeman or federal lawman ever discovered it.

But by 1960, Helen was in serious trouble for the first time in her life. Her beauty had faded long ago, and she could no longer use it to get herself out of a jam. To maintain the floundering tavern, she borrowed a large amount of money from a loan shark at an exorbitant interest rate. She owed thousands in back taxes and the government eventually cut her Social Security payments. The few remaining friends she had held a benefit party to raise part of the necessary cash. The loan shark forgave the loan when two hit men sent by the Chicago mob came to kill him. 

The years of standing behind a bar for 18 hours a day led to serious health issues from varicose veins. In 1965, she told her life story to ghostwriter Robert Dougherty. Upon publication, her autobiography sold 100,000 copies and was reprinted several times. Helen saw very little of the money, but it was enough to carry her for the remaining three years of her life. She moved into the former Muir sanitarium on the county grounds in Wauwatosa. The legendary Dirty Helen Cromwell passed away on May 21, 1969, at the age of 83. No doubt Helen would be thrilled to know that she and her infamous tavern are forever woven into the tapestry the comprises the history of Milwaukee.