The Chicagoan Recipe

Build and stir

Chill a rocks glass by filling with ice or placing in the freezer for a few minutes. In a mixing glass add 2 oz rye whiskey, 1 oz rotating amaro, 3 dashes black walnut bitters and 1/4 tsp demerara or rich simple syrup if you prefer a touch of sweetness. Fill the mixing glass with large, fresh ice.

Stir for dilution

Using a bar spoon, stir the mixture briskly for 20–30 seconds (roughly 20–30 full spoon rotations) until the outside of the mixing glass feels cold and the liquid is properly diluted and slightly viscous. Aim for about 20–25% dilution of the spirit volume for a well-balanced sip.

Prepare glass and garnish

Discard ice from the chilled rocks glass. Place a single large ice cube in the glass. Express the oils of one orange peel over the stirred cocktail by holding the peel over the glass with the outer (colored) side down and giving it a firm twist to spray oils across the surface; then rub the rim with the peel and drop it into the glass as garnish.

Strain and serve

Double-strain the stirred mixture from the mixing glass into the prepared rocks glass over the large ice cube using a julep or hawthorne strainer (and a fine mesh if desired) to catch any small chips of ice or citrus. Serve immediately.

Notes on rotating amaro

The recipe calls for a "rotating amaro" — choose one amaro to feature and rotate periodically for different flavor profiles. Suggestions: Averna (mild, caramel & chocolate), Montenegro (bright, orange & floral), Cynar (artichoke bitterness, vegetal), Nonino (grapey, bittersweet), Amaro Lucano (herbal, balanced). Each will shift the cocktail's balance; you can adjust the optional syrup by ±1/8–1/4 tsp to taste.