The Chicago Handshake is not mixed, not stirred, and not, by most honest accounts, pleasant on the first attempt. It pairs a shot of Jeppson's Malört — the famously punishing Chicago wormwood liqueur — with a cold can of Old Style, the lager long tied to the city's ballparks and corner taverns. You drink the shot, you chase it with the beer, and you have effectively shaken hands with the town. It is less a cocktail than a rite of passage, and it is documented here in that spirit.
The first shot is a dare; the beer that follows is the apology.
A Chicago Ritual
Jeppson's Malört is a bäsk — a Swedish-style wormwood liqueur — brought to Chicago by immigrant Carl Jeppson, who reportedly kept selling it through Prohibition on the logic that something this bitter could only be medicinal. For decades it was a strictly local curiosity, the brand passing through the Carl Jeppson Company and, eventually, Chicago's CH Distillery, which acquired and revived it in 2018. Old Style, brewed by G. Heileman and now under Pabst, carried the same hometown loyalty, pouring at Wrigley Field for generations.
The pairing of the two — a Malört shot and an Old Style — got the name Chicago Handshake in the city's bars sometime in the early 2010s. The exact coinage is uncertain and we will not pretend otherwise; it spread through bartender lore and the internet rather than from a single documented inventor. What is certain is that it stuck, becoming the standard way for a Chicago bar to welcome — or haze — a newcomer.
The Spec
There is no technique to hide behind here, which is the point. A standard 1 1/2 oz pour of Malört goes in a shot glass; a cold Old Style stands beside it. The only real decision is the order, and even that is settled by tradition: the shot first, the beer as relief.
Why Malört, specifically
Any bitter spirit would technically chase, but the Handshake is Malört or it is nothing — the joke and the local pride both depend on the brand. Its grapefruit-pith, gasoline-and-wormwood finish is the entire performance; a smoother amaro would defeat the purpose. If you cannot find it outside the Midwest, the drink simply does not travel, and that, too, is part of the legend.
Why Old Style earns its place
The beer is not garnish. A light, dry American lager does the real work, scrubbing the wormwood off your palate fast enough to let you keep talking. Old Style is the canonical choice for civic reasons, but any cold, cheap, unfussy lager honors the spirit of the thing. A heavy IPA would only get in the bitter's way.
The order is the technique
Shoot the Malört first, while your resolve is fresh, then reach for the Old Style. Sip the beer between rounds rather than gulping it; the lager is the long game and the shot is the short, sharp opening. Done right, the whole thing is over in a breath and remembered for considerably longer.
Bottom Line
The Chicago Handshake is a regional handshake in the literal sense: a small, deliberately uncomfortable gesture that means you belong. It will not win a cocktail competition and was never meant to. Order one when you want to taste a city's sense of humor about itself — bracing, self-deprecating, and gone before you can change your mind.