The Bootleg: Minnesota's signature country-club cocktail

Prohibition-era drink deftly masks taste of alcohol

I first heard about the Bootleg from Dean Phillips, of Phillips Distilling, who told me he'd served the drink at the Food & Wine Classic festival in Aspen to introduce Phillips's Prairie Organic Vodka. The Bootleg, Phillips explained, paired the vodka with citrus and fresh mint—several Minnesota country clubs served it.

A short while later, I was on the phone with Joe Kaplan of Joe's Garage when he mentioned that the Bootleg was his favorite summer sipper. And how had he been introduced to it? Back when Minnesota's drinking age was 18, Kaplan said, he spent many hot summer days at the Minikahda Club, where his friend's family had a membership. "We'd hang by the pool and look at girls and drink Bootlegs," he recalled.

You know how they say things come in threes? Well, shortly thereafter, one of my friends came back from his friend's cabin and wanted to tell me about a new drink he'd tried. "Let me guess," I said. "The Bootleg?" Apparently, my friend's friend had acquired the special Bootleg mix from his parents' country club. My curiosity was piqued: What was this secret country-club cocktail, and how could the rest of us get our hands on it?

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When I started calling local country clubs to inquire about the Bootleg, I got some funny responses. Two people started laughing, a third let out an intriguing "Oooh," and a fourth said, "Oh, wow, cool." When I told Mark Smiley, of Interlachen Country Club in Edina, that I was calling about the Bootleg, he paused and replied, "Somehow I knew you were going to ask about that. I've been pouring a million of them in the years I've worked here."

I wasn't so much concerned with the millionth Bootleg as with the first one, so I quizzed all the club managers about the drink's origin. Turns out the Bootleg shares a few characteristics with the Jucy Lucy: It's deeply imbedded in Twin Cities culinary culture—and more than one local establishment claims to have invented it.

Jim Sargent, the clubhouse manager at Woodhill Country Club in Wayzata, told me that he believed the Bootleg originated there. "I'm only the fourth person to be making the mix in the last 80 years or so," he explained. His understanding was that the recipe began with a Woodhill bartender named Walter who, during Prohibition, had invented it while working for a men's card club. (Walter had also worked at the now-defunct Charlie's Café Exceptionale, which at one time was the finest place to eat in Minneapolis.) Walter had passed Bootleg mix duties on to a man named Mike, who passed it on to another man named Jim, who made it for decades before letting Sargent in on the secret. "One person is the mix master," Sargent continued. "And they pride themselves on theirs being slightly better than everyone else's."

But then I talked to George Carroll, the general manager of Interlachen, who told me that he believed the Bootleg had come from Somerset Country Club in Mendota Heights, where his wife, Linda, used to work. Carroll recalled a bartender named Danny Stevens who had introduced the Bootleg to the Minikahda Club in Minneapolis. Stevens was also the bar manager at Pracna on Main, where he made batches of the mix and supplied it to other restaurants, including Lord Fletcher's. "Now if you go in there and ask for a Bootleg, they probably wouldn't know what you're talking about," Carroll said. (Carroll's hunch was correct. I called both Pracna and Fletcher's, and neither seemed to know anything about the Bootleg.) For whatever reason, Stevens's Bootleg never spread through the local restaurants. "It left with him, and he never told anybody the recipe," Carroll added. "And that was 30-some years ago."

So I called Somerset, hoping to learn more. The folks there confirmed that they believed the original Bootleg was created there, during Prohibition, by a bartender named Al Dunst—but that was all they knew. So I contacted Linda Carroll, who now manages at the White Bear Yacht Club, to see if she could give me more details. But instead of confirming the Somerset claim, Carroll offered a new twist. "My members swear it was originally made here," she said. "And I think they're probably right." Her suspicions were based on the fact that the White Bear club is one of the oldest in town—it celebrates its 120th anniversary this year.

I was hoping that, in the course of my inquiries, some retired bartender might lead me down a dark staircase, crack open a creaky safe, and procure a stash of handwritten recipes, photographs, or some other documentation that would prove his club had invented the drink. So far, no such luck.

Jay Fritzke, the clubhouse manager at Wayzata Country Club, was the first person I spoke with who claimed the superior Bootleg recipe. "We have the best," Fritzke boasted. "That's been known for some time." He says the club recently tweaked the drink's formula to sweeten it up, and since then it's become even more popular. "On a hot day there's nothing better," he said.

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