American Trilogy

whisky/brandy old-fashioned, US-American style.
1 oz Applejack
1 oz Rye
14 oz Grade A dark amber maple syrup
2 ds Orange bitters
1 twst Orange peel (as garnish)
Combine liquid ingredients in a rocks glass. Stir with ice. Garnish with twist of orange peel.
Based on a cocktail developed at Little Branch in New York City.
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Sasha Petraske founded both

Sasha Petraske founded both Milk & Honey and Little Branch.

The cocktail's co-creators are Richard Boccato and Michael McIlroy.  They both worked at both bars. But Little Branch probably deserves the nod. In Regarding Cocktails, Boccatto's quote about this drink:

Once in the midst of a sleepy shift at Little Branch, I asked Mickey whether or not a cocktail could be built in the glass and devised with ingredients that were slightly different from those that we used to make our house Old Fashioned.

This is a modern classic & I'd think Bocatto & McIlroy's original version (rather than the minor alterations made in PDX) should be found somewhere here.