In the world of bourbon, few names carry as much weight as Van Winkle, a family synonymous with some of the most coveted whiskeys ever made. But there’s another story tied to their legacy that’s just as compelling—one that involves a fiery speakeasy operator, a notorious gangster, and a bourbon that’s making waves in 2025. Old Commonwealth Distillery, a Kentucky-based operation with deep historical roots, has brought back a legendary name with its D.H. Cromwell 15 Year Bourbon. This limited-release whiskey isn’t just about great taste; it’s a tribute to a bold woman from the Prohibition era and a chance to support a meaningful cause.
The Revival of Old Commonwealth Distillery
Old Commonwealth Distillery has a storied past. Originally established in 1889 in Lawrenceburg, Kentucky, the distillery operated under various names, including Hoffman Distillery and Ezra Brooks. For a time, it was closely tied to the Van Winkle family, who used the facility to produce their iconic whiskeys until 2002, when Buffalo Trace acquired the operation and shut it down. But in 2024, Old Commonwealth roared back to life, reviving historic brands with a mission to let people “drink history,” as Zachary Joseph, the distillery’s president of operations, puts it.
Image credit: Old Commonwealth Distillery
The distillery’s second expression in less than a year is the D.H. Cromwell 15 Year Bourbon, a whiskey that pays homage to a colorful figure from America’s past. Unlike the distillery’s earlier Colonel Randolph release, which celebrated a vintage mash bill, this bourbon tells a story of rebellion, grit, and redemption.
Who Was “Dirty Helen” Cromwell?
The D.H. in D.H. Cromwell stands for “Dirty Helen,” a nickname earned by Helen Cromwell, a woman who lived life on her own terms from 1886 to 1969. Born in a time when women’s roles were tightly constrained, Cromwell carved out a place for herself in Milwaukee’s underbelly. She was a sex worker, a madam, and, most famously, the proprietor of the Sunflower Inn, a speakeasy that thrived during Prohibition. Her bar was a magnet for a diverse crowd—politicians, professional athletes, everyday workers, and even notorious figures like Al Capone, who reportedly counted her among his acquaintances.
Cromwell’s nickname came from her sharp tongue. She was known for hurling insults at customers who dared ask for anything other than whiskey—Scotch or bourbon only, please. Her unapologetic attitude and fearless spirit made her a legend. “Helen Cromwell was too bold to be polite and too loud to be ignored,” Joseph says, explaining why the distillery chose her name for this release. “Her personality matches the bourbon we’ve crafted—pure, bold, and unforgettable.”
But there was more to Cromwell than her tough exterior. During the Great Depression, she used her wealth to help others, paying tuition for young men who went on to become doctors and lawyers. She also supported the women who worked for her, offering them funds to attend Marquette University. This blend of toughness and generosity inspired Old Commonwealth to not only name their bourbon after her but also to tie it to a charitable cause.
Crafting the D.H. Cromwell 15 Year Bourbon
Creating a bourbon worthy of Helen Cromwell’s name was no small task. Aging bourbon for 15 years in Kentucky’s hot, humid climate is a challenge, as the intense weather can amplify oak flavors, sometimes overpowering the whiskey’s other notes. To get it right, Old Commonwealth’s team, led by Joseph, spent six months tasting over 100 barrels from an undisclosed heritage distillery. After rigorous evaluation, only four barrels were deemed exceptional enough to become D.H. Cromwell 15 Year Bourbon.
Image credit: Old Commonwealth Distillery
The selected barrels were re-barreled in new, charred oak from Kelvin Cooperage for an additional six months, a process that added a distinctive fruity, red candy note reminiscent of vintage whiskeys. The final product has a mash bill of 75% corn, 13% rye, and 12% malted barley. The team tested it at cask strength and 110 proof but ultimately settled on 106 proof, which they felt best showcased its complex flavors.
In the glass, the bourbon glows a deep copper, hinting at its long aging. The aroma opens with an earthy note, followed by inviting scents of vanilla frosting, caramel, and orange peel. On the palate, it’s surprisingly light, delivering a burst of cinnamon candy, baking spices, ginger, and orange zest, with just enough oak to ground the experience. The finish is where it shines, lingering with fudgy dark chocolate, cherry, citrus, and a subtle herbal touch. “It’s a whiskey that feels like it’s from another era,” Joseph says, noting its vintage character despite being a 2025 release.
A Nod to Gordon Jackson’s Legacy
This isn’t the first time Helen Cromwell’s name has graced a bourbon bottle. In 2000, Louisville liquor retailer Gordon Jackson won a barrel of 15-year-old bourbon from Julian Van Winkle III, a wheated whiskey with an unusual 92.4 proof. Enamored with Cromwell’s story, Jackson bottled it as D.H. Cromwell—after the federal government rejected his original plan to call it “Dirty Helen Cromwell.” Only 72 bottles were produced, priced at $60 each. At the time, they sold slowly, as bourbon hadn’t yet reached its current fever pitch of popularity.
Today, those bottles are collector’s items, fetching upwards of $18,000 at auction. While Old Commonwealth’s 2025 release isn’t a wheated bourbon like Jackson’s, it carries the same spirit of honoring a larger-than-life figure. Unfortunately, comparing the two side-by-side is a dream for most whiskey fans, given the rarity and cost of the original.
A Limited Release with a Purpose
Old Commonwealth’s D.H. Cromwell 15 Year Bourbon is as exclusive as it is flavorful. Priced at $299, it will go on sale May 22, 2025, through the distillery’s website, with Old Commonwealth VIPs getting first dibs via an emailed alert. Non-VIPs will need to act fast, refreshing their browsers or checking select retailers in Illinois, Tennessee, and Kentucky. Given the hype around limited releases and the distillery’s growing reputation, bottles are likely to disappear quickly.
What sets this release apart is its charitable component. A portion of the proceeds will support Refuge for Women, an organization dedicated to helping sexually exploited and trafficked women rebuild their lives. The choice reflects Cromwell’s own legacy of supporting those in need, particularly women. “Helen used her resources to empower others,” says Andrew English, Old Commonwealth’s co-founder. “We’re honored to continue that tradition in her name.”
Why This Bourbon Matters
The D.H. Cromwell 15 Year Bourbon is more than just a whiskey—it’s a celebration of history, resilience, and redemption. It connects the Van Winkle family’s legacy to a woman who defied the odds in a male-dominated world, all while delivering a sipping experience that rivals the best bourbons on the market. For collectors, it’s a chance to own a piece of Old Commonwealth’s revival. For casual drinkers, it’s an opportunity to taste a whiskey that tells a story with every sip.
But it’s also a reminder of the power of giving back. By supporting Refuge for Women, Old Commonwealth is ensuring that Helen Cromwell’s legacy of helping others lives on. Whiskey fans hoping to snag a bottle will need luck and quick fingers, but those who succeed will have more than just a great bourbon—they’ll have a piece of history and a chance to make a difference.
