The Bootleg: Minnesota's signature country-club cocktail

Prohibition-era drink deftly masks taste of alcohol

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."

The infamous Bootleg: The upper crust's secret summer sipper
Megan Thompson
The infamous Bootleg: The upper crust's secret summer sipper
"John F. Scott": Was Fitzgerald a Bootleg fan?
Megan Thompson
"John F. Scott": Was Fitzgerald a Bootleg fan?

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." 

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