In 2000, when Louisville liquor retailer Gordon Jackson won a full barrel of 15 year bourbon from Julian Van Winkle III, Jackson immediately knew how he wanted to bottle and sell the whiskey: under the name “Dirty Helen” Cromwell.

Helen Cromwell — Jackson rightly believed — is a legend. Born in 1886, Cromwell lived a hedonistic life of reckless abandon: sex worker, madam, speakeasy operator, and finally, from the 1920s through the 1940s, the iron-fisted proprietor of Milwaukee’s infamous Sunflower Inn. 

There, Cromwell only served whiskey — Scotch or bourbon — and a pile of foul-mouth insults to anyone who asked for alternative imbibes, hence the sobriquet “Dirty Helen.” Enamored with Cromwell’s brazen, unrepentant escapades, Jackson believed Van Winkle’s first single barrel bourbon the perfect embodiment to honor the queen of grit.

A scant 72 bottles of D.H. Cromwell — the federal government rejected the originally proposed name of “Dirty Helen Cromwell” — were produced, a wheated 15 year Kentucky bourbon that had an unusual proof of 92.4. An artistic friend of Jackson’s designed the askew label, including the letters “VGS” at the bottom, an old wine term that stands for “Very Good S**t,” a phrase Jackson found particularly fitting in this application. 

Priced around $60, Jackson recalls the bottles moving slowly, though all eventually sold. Today, remaining D.H. Cromwell bottles hammer for more than $18,000 each at auction.

Now, 25 years after its initial release, Old Commonwealth is pleased to announce D.H. Cromwell is back.

Creating Old Commonwealth’s 2025 D.H. Cromwell 15 Year Bourbon

For the executive team at Old Commonwealth, the exploits of Cromwell (more on those momentarily) and the striking aesthetics of the bottle were key factors in the decision to resurrect this revered brand. 

“Every Helen story makes you laugh. She was so wonderfully unapologetic and brash,” Zachary Joseph, president of operations for Old Commonwealth, said in a news release. “That’s what we think about our Old Commonwealth whiskey: pure and bold. Helen would’ve been a fan of our whiskey, just as we’re immense fans of her incredible life story.”

For whiskey befitting Cromwell’s name, Joseph and his team sourced 15 year Kentucky straight bourbon from a heritage distiller. After trying more than 100 barrels for half a year, four barrels were deemed worthy. Unlike the original wheater, the 2025 D.H. Cromwell bourbon has a mashbill of 75 percent corn, 13 percent rye, and 12 percent malted barley. 

“We’re harkening back to earlier iterations of our facility, when all the attention was on blending and finishing elements,” Joseph said. “The process for D.H. Cromwell was to re-barrel the bourbon in new, charred oak barrels from Kelvin Cooperage for six months, giving it that fruity, red candy note we associate with vintage whiskey.”

After blending, it was sampled at cask strength, then at 110 proof, and finally at 106 proof; the latter won out. SRP is $299.

In addition to the final blend tasting superior to the individual single barrels, “we want more people to have access to our products,” Andrew English, co-founder of Old Commonwealth, said. “We hear our fans asking for higher volumes. We’re listening and trying to accommodate.”

From Prohibition Rebel to Whiskey Icon: Inside Helen Cromwell’s Wild Life

The antics detailed in Cromwell’s 1966 autobiography are as incredible as the book’s title: “Dirty Helen: A Zany, Wonderful, Unconventional Ex-Madam and Tavern-Keeper Tells of Her Adventures, the Fascinating People She Has Known and The Exploits That Make Her a Living Legend.” (Say that three times fast.)

Born Helen Worley in 1886 in Louisville, Kentucky, Cromwell—the surname of one of her six husbands—lived fast, hard, always with a whiskey in hand, and she rarely said no. This approach resulted in eye-popping scenarios:

• Accompanying an infamous bank robber to the Colorado mountains to hide for a summer while the heat died down from the last heist
• Getting shot in the leg by an angry wife of a former indiscretion
• Taking a cab from Milwaukee to Cincinnati wearing nothing but a fur coat
• Stumbling into sex work after bedding a man who left her $50 in her hat following their romantic interlude
• Working as an undercover madam for mobster Al Capone to suss out whether his regular madam was skimming cash (she was)
• Asking Capone to accompany her to a divorce proceeding to scare her abusive, soon-to-be ex into submission (it worked) 

During Prohibition, Cromwell ran a popular speakeasy and brothel in Wisconsin, drumming up business by renting a luxury convertible and driving down main street throwing hundreds of dollar bills to a rabid crowd, suggesting they come drink at her establishment. 

When Prohibition ended, her haunt was legitimate, now called the Sunflower Inn, and it was a melting pot for Milwaukee’s hoi polloi and upper crust. Gangsters, pro baseball players, politicians, and regular Joes all mingled together. Her booming business only flourished as her foul-mouthed “Dirty Helen” persona grew. Theatrically cussing out customers was met with thunderous applause.

Cromwell was exceptionally charitable, both to women who worked in her brothel and to strangers. Sob stories from patrons about being unable to afford nearby Marquette university led to Cromwell paying their ways. 

“I was loaded with dough and I think I put it to good use in the early Thirties,” Cromwell wrote. “I’ve paid many a tuition bill for boys who are now doctors and lawyers.”

Every D.H. Cromwell Bottle Gives Back

“Helen may have drank like a rebel, but she gave like a saint. Helen did a lot for the people of her community, so it’s important for us to give back too,” English said. “We’re excited to partner with Refuge for Women, a charity organization that helps empower sexually exploited and trafficked women to live a life of freedom. We’re donating a portion of the proceeds from the sale of each D.H. Cromwell bottle to this wonderful organization. We imagine Helen would’ve appreciated Refuge for Women’s mission and accomplishments.”

Operational in Texas, Nevada, Illinois, and Kentucky, Refuge for Women uses three types of residential healing programs to help women coming out of strip clubs, escorting, the pornography industry and more. Women fresh out of their situation detox and stabilize in emergency housing, before moving to long term housing and healing, then a transitional living phase where they learn job skills and prepare for a life outside of refuge. All portions of the program are free to the residents, funded by donors and grants.

“Having had similar experiences to Helen for ten years and having walked with women in the commercial sex industry for 24 years, I know first-hand that many would have left if they had the hope, support, and tools to live a life of freedom and flourishing,” Deanna Lynn, executive director of Refuge for Women Kentucky, said. “I’m so thankful to have graduated from Refuge for Women myself in 2012 and to have the privilege to support my sisters ready to escape and start again.”

Old Commonwealth’s 2025 D.H. Cromwell 15 Year Bourbon will be released on its website — oldcommonwealth.com — on Thursday, May 22. The exact drop time will be emailed to OC VIP members the evening before (sign up is free). Old Commonwealth’s online shipping partner is able to service customers in 40 states. Select stores and retailers in Illinois, Tennessee, and Kentucky will have limited quantities available.

Read more: Old Commonwealth to Release 16-Year Colonel Randolph Bourbon

About Old Commonwealth Distillery

Originally built in 1889, in Lawrenceburg, Kentucky, the Old Commonwealth Distillery has been home to Hoffman Distillery, Ezra Brooks, and Commonwealth Distilling over the past 135 years. In 2019, it was purchased by Zachary Joseph and Andrew English, a nephew and uncle who bonded over the distillery’s history and its venerable products. Along with family friend and partner Troy LeBlanc, the trio are reviving iconic labels once produced there, and preserving the facility’s heritage through immersive tour experiences. For more information, visit https://shop.oldcommonwealth.com/.