The Story Behind The American Trilogy

From the film world to horse racing, there's a reason trilogies are a mainstay — things that come in threes just feel epic and complete. That's also true in the beverage world, and a prime example is the American Trilogy, a cocktail that documents the nation’s early days of distillation in one glass. The Old Fashioned riff, created in 2007 by Richard Boccato and Michael McIlroy at New York City’s Little Branch, combines orange bitters with two notable spirits: applejack, the first distilled spirit in the country, and rye whiskey, the original American whiskey.

Like many modern classics, this drink evolved from a pre-existing template. Boccato and McIlroy replaced the original Old Fashioned build’s bourbon with a hearty split-base of rye and bonded applejack. The duo also added brown sugar to the cocktail to sweeten up the cocktail and balance its boozy intensity.

Chefs and mixologists often say, “if it grows with it, it goes with it,” and the historic ingredients in the American Trilogy are no exception. Applejack traces back to the early 1700s when Laird & Company was founded in Scobeyville, N.J. Originally made via an unrefined process called “jacking” in which apple distillate is frozen and excess water is then removed, our modern, commercial applejack production involves distilling fermented cider and mellowing it out in oak barrels. The spirit finds itself in a number of classic cocktails like the Jack Rose, the Widow’s Kiss, and the Diamondback. While some applejack is made from a blend of apple brandy and neutral grain spirits, bonded applejack is 100 percent apple brandy, imparting baked apple and caramel notes on this cocktail.

Around 1750 and shortly after the advent of applejack, rye whiskey distillation began in Pennsylvania when Scottish and Irish immigrants attempted to recreate the whiskeys of their homelands with American grains. Due to the abundance of rye grain in Pennsylvania and  neighboring states, it became the go-to grain for whiskey production. In the early 1800s, early American cocktail culture started forming, and with that came the first commercially available aromatic bitters courtesy of the Angostura brand. Orange bitters made their commercial debut later that century. In this cocktail, the bitters add a citrus peel-like undertone to the rye’s assertive spiciness.

Boccato made the American Trilogy the house Old Fashioned at his own Queens bar, Dutch Kills, and McIlroy still frequently serves up the cocktail at his bar, Attaboy, which he co-owns with fellow Milk & Honey alum Sam Ross. When stirring up the drink, we recommend straw tasting the cocktail to periodically check in on the level of dilution.


  • 1 ounce bonded applejack
  • 1 ounce rye whiskey
  • 1 brown sugar cube
  • 2 dashes orange bitters
  • 1 splash of soda
  • Garnish: orange twist


  1. Add a brown sugar cube, bitters, and a splash of soda to an Old Fashioned glass.
  2. Gently muddle into a granulated paste.
  3. Add applejack, whiskey, and a large ice cube.
  4. Stir until the paste is dissolved and the cocktail is chilled.
  5. Express an orange twist over the glass, then garnish.

Rate This Recipe:

(39 votes)

Yield: 1
Calories: 155
Updated: 2024-05-06

American Trilogy Recipe Video