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?
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.
There's a surprising amount of variation in Bootleg recipes, considering it's such a simple drink. For the citrus component, some use fresh-squeezed juice, while others use concentrate. Most recipes call for lemonade or a lemonade-limeade blend, though a few use sweet-and-sour mix. Sometimes the mint is muddled, other times it's blended. A couple of the clubs make each drink individually, but most make up batches of the mint-citrus mix ahead of time. The most common version of the Bootleg is served in a pint glass filled with ice, though a few clubs blend the drinks until they're slushy.
Jim Sargent told me that in the early days, Bootlegs were mixed with gin, but that today the alcohol of choice tends to be vodka. Some people, he said, add bourbon or rum. "People mix Chardonnay with it, believe it or not," he noted. And the virgin version? It's called Bootade, of course.
The Bootleg's refreshing nature makes it similar to a daiquiri, a margarita, or a mint julep, though it's probably most closely related to a mojito or the Southsider, a popular East Coast drink suspected to have originated during Chicago's gangster days. One of the Bootleg's defining characteristics is its ability to mask the taste of the alcohol entirely—an important quality if the drink indeed originated during Prohibition, as most drinkers could only get their hands on rotgut alcohol. The Bootleg can get a little "dangerous," more than one manager noted. "You can't taste the alcohol in 'em," George Carroll said. "And it's possible to drink too many on a hot summer day and not know what's going on."
Carroll also points out the Bootleg's big downside: "You smile and you've got the mint in your teeth. People know what you're drinking." Darrell Scharber, the bar manager at Oak Ridge in Hopkins, solves that problem by blending the mint with sweet-and-sour mix and then straining out the flecks. One more secret to Scharber's 30-plus-year-old recipe: He adds a couple of drops of green dye to the mix. "Otherwise it looks like swamp water," he explained.
Some clubs consider their Bootleg recipe top secret, but others happily share it with their members. Town and Country offered me theirs, which I'll pass on, in case you'd like to make Bootlegs at home.
To make the mix, combine 32 ounces of Sunkist frozen lemonade and a handful of fresh mint leaves (no stems) in a blender and mix. Add 1 to 1.5 ounces of vodka, rum, or gin to 2 to 3 ounces of Bootleg mix, then top with an ounce or two of club soda. (Some prefer 7-Up or Sprite.)
Even when club members know the recipe, they'll often buy the mix from the club instead of making it themselves. One manager estimated that he makes close to 120 quarts of mix a week. He's overnighted the stuff halfway across the country to snowbirds wanting a taste of home.
According to Colin Knudtson, of the Lafayette Club in Wayzata, many clubs consider the Bootleg their signature drink. "In the private club it's kind of like a guarded secret," he said. "Everyone has their own opinion, and they think they have the greatest Bootleg around." At the Lafayette Club, he said, the Bootleg is the best-selling summer drink. Part of the Bootleg's allure is that the club only serves them seasonally. "People are begging for the drink before Memorial Day weekend," he said. "They ask, 'Do we have Bootlegs yet?'"
For whatever reason, Bootlegs rarely seem to show up outside of private clubs, though a few restaurants serve them. Joe's Garage makes one, as do W.A. Frost and Brit's Pub (one of Brit's owners is a longtime Minikahda member). None of the managers I talked to had heard of a Bootleg being served outside the Twin Cities, except in the rare case of a former Twin Cities manager who had moved to a club in another state and introduced it there. Why hasn't it spread beyond the private clubs? "I don't know," said Jay Fritzke of Wayzata. "It's just one of those things. It's old and it's traditional. Lots of parents of members drank them and passed it along to their kids."
Hoping to recreate the Bootleg's heyday, I sipped one at St. Paul's University Club, at the old wooden bar that was once autographed by its members—one of the signatures, which reads "John F. Scott," was supposedly penned by F. Scott Fitzgerald. I'd heard the Bootleg was Fitzgerald's favorite drink, though I have my doubts that such a notorious drinker would have bothered with something so sweet. The University Club's bartender told me that Fitzgerald's drink of choice was a gin martini with a black olive, served neat. But, he added, in the summer Fitzgerald apparently drank gin rickeys—a lime-based cocktail that's not so different from the Bootleg.
The University Club makes its Bootleg with muddled mint and fresh-squeezed lemonade—I prefer its subtlety to the concentrate blend, actually. I looked out over the leafy green treetops knowing that the view below me would soon transition to its autumnal golds, oranges, and reds. My drink—liquid summer in a glass—was a manifestation of an all-too-short season. I sensed that one of Jim Sargent's remarks about the Bootleg would soon ring true. "As winter weather comes," he said, "it just doesn't taste right."