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Michael Bilandic and the cocktail he inspired.

One-term Mayor Michael Bilandic’s downfall in 1979 has become a cautionary tale to future would-be mayors of Chicago: Always make sure the snow gets plowed. His chilly defeat inspired this iced cocktail.

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William Hale “Big Bill” Thompson and the cocktail he inspired.

William Hale “Big Bill” Thompson was arguably the most corrupt politician Chicago has ever seen. He inspires a bourbon-based cocktail topped off with a taste of Chicago.

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It’s never been easy or popular in America to be an egghead. Just ask Adlai Stevenson, who once remarked, “the way of the egghead is hard.” For a drink befitting Stevenson’s balance and brainpower, we create the Old Shoe from equal parts Old Tom gin, vermouth and applejack.

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We honor Anton Cermak’s immigrant story with a Chicago-brewed Czech pilsner, Revolution Brewing’s Rev Pils, and spike it with the spirit of a more recent group of Chicago immigrants: tequila.

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We toast Chicago’s first mayor with a drink that gives a nod to William B. Ogden’s influence on city bridges and railroads: the Boilermaker.

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This week, we raise a glass to five-time U.S. Congressman and two-time U.S. Sen. Paul Simon, the O.G. hipster of the Senate, with a new twist on an old-school cocktail.

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Longtime U.S. Congressman Dan Rostenkowski famously called Chicago politics “blood sport.” We raise a glass to one of Chicago's own (who also happened to have one of the all-time great heads of political hair) with a Polish twist on a classic cocktail.

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Whether it was dancing with a polka queen or meeting with protesters, Mayor Harold Washington was always smiling. We celebrate Chicago’s first and so far only African-American mayor with the signature drink, How’s Harold?

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Chicago’s early history has a surprising amount of Kentucky in it, including five-time Chicago Mayor Carter Henry Harrison. We honor Harrison’s old Kentucky home by putting a Chicago spin on the classic mint julep.

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Forty years after Richard J. Daley’s death, Chicago still identifies itself with the man who steered it for more than two decades. Belly up to the bar and get a little taste of Chicago’s spirited history: an Irish whiskey and smoky mezcal blended drink.

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Following a whopper of a blizzard in 1979, Sauganash native Jane Byrne narrowly upset Mayor Michael Bilandic for the Democratic mayoral nomination. Belly up to the bar and get a little taste of Chicago’s spirited history: a frosty milkshake spiked with whiskey and vodka.

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Last week, we introduced you to the Hinky Drink. For our second installment, we’re saying “cheers” with the Lord of the Levee drink, inspired by Aldermen “Bathhouse” John Coughlin and Michael “Hinky Dink” Kenna.

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Belly up to the bar and get a little taste of Chicago’s spirited history. We're raising a glass to Michael “Hinky Dink” Kenna, who famously crowed “Chicago ain’t no sissy town.”

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