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How a Motley Crew of Bartenders Transformed Chicago’s Drink Scene

With an opening team of mostly amateur bartenders, The Violet Hour defied odds to reshape Chicago’s drinking scene. Robert Simonson on the bar’s unlikely beginnings and its enduring legacy.

Students of the cocktail renaissance like to talk about family trees, tracing each bartender back to the mentor or bar that first forged them. In London, nearly every road leads back to Dick Bradsell, the late godfather of the British cocktail revival. In New York, many barkeeps can be assigned to the schools of Sasha Petraske (Milk & Honey), Julie Reiner (Flatiron Lounge, Clover Club) or Audrey Saunders (Pegu Club)—all of whom were mentored, to some extent, by Dale DeGroff.

In Chicago, The Violet Hour—the trailblazing cocktail bar that opened ten years ago this month—is the mother of local mixology. “The Violet Hour pioneered the prevalence of using spirits outside the mainstream vodkas, gins and rums,” says Mike Ryan, the director of bars for the Kimpton hotel chain. “It set the standard by which every other bar judged its cocktails.”

Ryan, who first made his mark running the cocktail program at Chicago’s Sable Kitchen & Bar, is just one of the many VH bartender alumni who currently hold sway over the Windy City’s drinking scene. Other veterans include Bradley Bolt, owner of Bar DeVille; Kyle Davidson, formerly of Blackbird, now at Elske; Michael Rubel at Estereo; Stephen Cole, first at The Barrelhouse Flat, then Lone Wolf; and Nandini Khaund, now behind the stick at Cindy’s, high atop the Chicago Athletic Association hotel.

If Chicago today has one of the strongest cocktails communities in the country, The Violet Hour can take a lot of the credit.

Furthermore, VH has the unusual distinction among cocktail bars of having influenced the bar landscape in other cities. Kirk Estopinal, a member of the opening bartending staff, left to join the team at Cure, the cocktail bar that forever changed the way New Orleans drinks. Susie Hoyt went on to run The Silver Dollar, one of Louisville’s leading cocktail bars. And Ira Koplowitz ended up making a big noise in Milwaukee, opening the bitters company Bittercube and consulting at various Midwestern watering holes.

All of the above transpired over the last ten years—a benchmark the Chicago bar is celebrating this month. But the seeds of The Violet Hour go well beyond 2007. They were planted back in the 1990s, when restaurateur Terry Alexander hired a young Coloradan drifter named Toby Maloney to work at his place Soul Kitchen.

“He was my first oyster shucker,” remembers Alexander.

The two remained friends, even after Maloney moved to New York and slowly mastered the art of craft cocktail bartending through stints at Grange Hall (alongside Del Pedro, an early figure in the New York cocktail renaissance, and now the owner of the Brooklyn bar Tooker Alley), Milk & Honey and Pegu Club. When Del Toro, Alexander’s tapas restaurant in Chicago’s Wicker Park neighborhood, closed, Maloney, along with partner Jason Cott, convinced Alexander to reopen the space as a cocktail bar.

Maloney plays down the impact of this decision. “All I did was bring Sasha, Julie, Audrey and Del to Chicago,” says Maloney, ticking off his mentors. “Everything fresh, good ice and attention to technique. And that’s really it.”

Also borrowed from Sasha Petraske’s Milk & Honey were the hard-to-find, unmarked entrance and a list of house rules: i.e., “No O-bombs. No Jager-bombs. No bombs of any kind. No Budweiser. No Light Beer. No Grey Goose. No Cosmopolitans.”

Simple enough. Only, not to Chicago, where drinking habits were simpler still. The city then was a meat-and-potatoes town, accustomed to beer and Malört shots and cheap tabs. Convincing customers to part with half a sawbuck for a gin drink, however carefully crafted, would be an uphill battle. But before Maloney even got a chance to try, he had to first convince his boss.

“I remember showing the coupe and sidecar I wanted to use to Terry Alexander,” recalls Maloney, “and him saying, ‘Yeah, that’s not going to work. We live in the baby-bassinet, 16-ounce Martini-land. This five-ounce glass is not going to work.’”

But soon enough, Alexander was on board, and Maloney set out to convert his bar staff. At the beginning of the first training session, he asked the bartenders who among them liked gin. “Nobody raised their hand,” he recalls.

It was a motley crew. The opening bartending lineup at VH included not a single person with cocktail-bartending experience, save one: Rubel, whom Maloney convinced to move from New York over a bottle of rum. Brad Bolt had bartended at restaurants and a nightclub. Estopinal and Cole were kitchen holdovers from Del Toro.

“We had cooks, we had baristas, we had servers” behind the bar, says Maloney. “We were building it from the ground up. We were exactly the opposite of Pegu Club, which had a murderer’s row of bartenders. [At VH] it was people who literally didn’t know what a jigger was.”

Maloney’s brand of Kool-Aid, however, was quickly sampled and consumed. A few weeks after opening, Maloney noticed that Cole had hung a poster inside his workplace locker. It was a chart detailing the origin of every brand of whiskey.

The opening cocktail menu was devised entirely by Maloney. After six months, though, his protégés began submitting drinks. In a few cases, the student became the teacher. When Davidson presented his drink, The Art of Choke, which had a split base of rum and Cynar, Maloney was dumbfounded.

“That drink ran against everything I taught him,” says Maloney. But people ordered it. Today, the cocktail is considered a modern classic.

After half a year, Alexander and Maloney no longer worried about finding bartenders. People approached them for jobs. Soon after that, VH’s first class of cocktail bartenders began to leave the nest. Bolt was first, departing in late 2007 to open Bar DeVille. Cole soon followed, launching Barrelhouse Flat. Meanwhile, other bartenders not affiliated with VH followed the bar’s lead. By 2010, Chicago had cocktail options aplenty. Many of these new joints, however, were cut from a different, more ragged cloth.

The Violet Hour “put the cocktail on a pedestal, for better or worse,” Bolt says, “but it eventually led to people like myself opening up more casual spots that still focus on making great drinks in an environment that is more relaxed and sometimes a bit rowdy.”

Kenney Marlatt, an editor at the Chicago Tribune who follows the city’s cocktail scene, experienced that shift from the other side of the bar. “An acclaimed bartender might describe the flavor profile of a particular Italian amaro as they crack open a High Life for a guest down the bar,” Marlett points out. “What The Violet Hour exported to the rest of the city was their standards, if not their style.”

The Violet Hour will mark their 10-year anniversary this fall by reuniting some of the old gang, who will return to a very different Chicago. In 2007, you could tally the town’s cocktail bars on two fingers: The Drawing Room and The Violet Hour. Today, you’d need two hands and both feet, and still not be done.

“Violet Hour was a breeding ground for drink makers… [who] secretly affect how you drink today in so many bars and restaurants throughout the city,” says Nandini Khaund. “Metaphorically, it was like being in the Illuminati.”

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