American Trilogy

The American Trilogy is what happens when two bartenders decide an Old Fashioned should have a thesis. Michael McIlroy and Richard Boccato built it in the Milk & Honey orbit in the mid-2000s by splitting the base between rye whiskey and applejack, sweetening with demerara, and finishing with orange bitters. It is a small change on paper and a large one in the glass: the apple brandy pulls the whole drink toward orchard fruit without ever making it taste like a flavoured whiskey.

Two Bartenders, One Bar, Two Dates

The drink comes out of the Milk & Honey school — Sasha Petraske's New York bar and the people it trained — and is credited to Michael McIlroy and Richard Boccato. Beyond that the record wobbles, and it is worth saying so. Some accounts put it at Milk & Honey, others at Little Branch, Petraske's follow-up bar where both men also worked. Dates split between 2006 and 2007. Nobody involved seems to have written it down at the time, which is how most bar-built drinks of that decade go.

What is not in doubt is the intent. This is an Old Fashioned rebuilt out of specifically American parts, and the name is the giveaway. The usual explanation for the "trilogy" is that the drink names three American ingredients: rye, the first whiskey distilled in the colonies; applejack, the first spirit distilled in them at all, made by freezing cider through New England winters; and orange bitters, in the form of the American-made Regan's No. 6. Read it that way and the name stops being a riddle. Read it as "three parts" and it will bother you forever.

The Spec

An even ounce of each spirit, a quarter ounce of rich demerara syrup, two dashes of orange bitters, stirred and served over one large cube with an orange twist. The demerara is doing more than sweetening — its molasses edge is what stops the applejack from reading as apple juice and keeps the drink in the same register as the Old Fashioned it is quoting.

Bonded applejack, and why it matters

Reach for bottled-in-bond if you can — Laird's is the one most people will find. Bonded means 100 proof, one distilling season, one distillery, four years in wood, and for this drink the proof is the point: a 40% apple brandy simply disappears under an ounce of rye. Laird's also sells an "Applejack" that is largely neutral grain spirit with a minority of apple brandy blended in, and it makes a noticeably thinner drink. Check the label for the word bonded or for a straight apple brandy, and if neither is available, a Calvados works and takes the drink somewhere drier and more rustic.

A 50/50 split is a real decision

Most split-base drinks lean — a base spirit with a modifier alongside it. This one refuses to. Equal rye and applejack means neither spirit is in charge, and the drink sits in a register that is not quite whiskey and not quite brandy. That is exactly what makes it interesting and exactly what makes it hard to guess blind. Tip the ratio to an ounce and a half of rye and you have made a decent apple-inflected Old Fashioned. You have also thrown away the reason the drink exists.

Orange bitters, not Angostura

Swapping the aromatic bitters for orange is the third leg of the substitution, and it changes the drink more than the small volume suggests. Angostura's clove-and-cinnamon weight would sit on top of the apple and flatten it; orange bitters lift it instead, and they meet the expressed orange twist at the surface so the nose and the first sip agree with each other. Regan's No. 6 is the reference and the one the name is pointing at.

Bottom Line

This is the Old Fashioned variation I make most often at home, and I think it is better than most of the famous ones. It costs you nothing but a second bottle, it teaches you what applejack is actually for, and it does the rare thing of being a history lesson that is also a good drink at eleven at night. Buy the bonded bottle.

The Old Fashioned Family