2025 D.H. Cromwell 15 Year Bourbon

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 exquisite 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.

For whiskey befitting Cromwell’s name, Zachary Joseph, Old Commonwealth’s president of operations, 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. Where it was made, per Joseph, is less important than what happens to the whiskey after procurement that makes it special and bespoke.

“We’re harkening back to earlier iterations of our facility, when all the attention was on blending and finishing elements,” Joseph says. “The process for D.H. Cromwell was to re-barrel the bourbon in new, charred oak barrels from Kelvin Cooperage for six months,” says Joseph, “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. “There’s a harmony at 106 that was exemplary,” says Joseph. “In several blind tastings, the 106 proof sample won unanimously.”