Recipe: The Ultimate Dessert Manhattan

updated Dec 17, 2019
Drink Recipe: The Ultimate Dessert Manhattan
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(Image credit: Christine Han)

This riff on a Manhattan isn’t your run-of-the-mill cocktail. No, it’s a special cocktail — one that should be made with care and sipped with some sense of occasion — and not just because of its ingredients, which (we’ll say in advance) may require a trip to the liquor store. This is a cocktail with a racy (or quite literally racing) past. You see, this cocktail was named after a Kentucky bookie and a bootlegger by the name of Jack Fry.

The Story Behind the Bootlegger Behind the Manhattan

If we had to guess, we’d say Kentucky has its fair share of bookies and bootleggers. But how many of those go on to become famous restaurateurs? We know, for sure, of just one: Jack “Malachi” Fry.

Jack Fry was a bootlegger who was also known to attend some sporting matches and horse races and wager a bet or two. Well, one of those bets (or perhaps two) paid off and Fry used the winnings to buy a restaurant in Louisville’s Highlands. He named it after himself (modesty, we’re guessing, wasn’t one of his virtues) and ran it with his wife, Flossie, for nearly 40 years.

During that time, Jack Fry’s evolved from a hangout for sports-lovers and bourbon-drinkers like himself into one of the city’s top fine dining establishments. And, after a brief interlude as a Mexican restaurant called Por Que No, today Jack Fry’s is carrying on its founder’s proud tradition of sports (through memorabilia) and booze (now legally).

(Image credit: Christine Han)

Malachi’s Manhattan, which takes its name from Jack’s middle name, is a riff on the Manhattan with a few notable swaps.

First, there is the vermouth. Here, it is not vermouth at all, but rather amaro — a type of Italian liqueur typically consumed post-dinner. The recipe calls specifically for Amaro Meletti, which is rich and almost chocolatey.

Then there is the addition of Giffard Vanilla Liqueur, which adds a warm, toasty quality. And finally, there is the substitution of black walnut bitters for the more traditional Angostura bitters, which lends the drink a nutty roundness.

All together the effect is a Manhattan that’s the ultimate dessert companion. We suggest a slice of Kentucky bourbon and walnut pie.

Drink Recipe: The Ultimate Dessert Manhattan

Makes 1

Nutritional Info


  • Ice

  • 2 ounces

    Bulleit Rye Whiskey

  • 1/2 ounce

    Amaro Meletti

  • 1/2 ounce

    Giffard Vanilla Liqueur

  • 4 dashes

    black walnut bitters

  • Luxardo cherry, for garnish


  1. Fill a cocktail shaker with ice. Add the whiskey, amaro, vanilla liqueur, and bitters. Stir until well-chilled. Strain into a martini glass and garnish with a cherry.

(Image credit: Rotem Raffe)