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This is a better cocktail than the similar but honey-sweetened De Rigueur Cocktail, as unless you have a very full-bodied honey, maple syrup's 'tang' sits...
I was actually surprised by how good this turned out to be. I was inspired by Roi's comment below and added a (heavy) barspoon of honey vinegar, which really brought more focus and clarity to the drink, without turning it into a sour. I used Yellowstone bourbon (eh). It starts off with maple flavors, and after a brief grapefruit detour, ends with bittersweet bourbon notes. Overall I found it highly enjoyable.
Made again with the exact same specs, but subbing honey for the maple syrup, and I much prefer the maple version. I found the maple to combine with the other ingredients in a way that was both more harmonious and more interesting, while the honey was kind of just there.
I've been enjoying a version of this that incorporates apple cider vinegar (2 ounces bourbon, 1 ounce grapefruit juice, 1/2 ounce each of honey syrup and apple cider vinegar). It's really well balanced.
You claim that the use of honey syrup in the Brown Derby is a 'misguided belief' which stems from the '33 book "Hollywood Cocktails," but the only evidence you've given that maple syrup was in the original recipe is a column published 6 years later in '39, which uses an entirely different spirit and citrus. Seems a little dubious. Made a rather nice cocktail nonetheless.
Perhaps there is an inference in Mr. Difford's review that the "1930 The Savoy Cocktail Book" describes a recipe for a Brown Derby with maple syrup but "when made with honey this is a De Rigueur cocktail"?
Fan of the original, but tried with reposado tequila (and a pinch of salt) in place of the bourbon and really enjoyed the result – like a short, sweet Paloma.
At first, I felt it was a bit too Bourbon forward for my taste. Then it turns out that I forgot 10ml of grapefruit juice. Added it after the fact and it was genuinely amazing from there. The tartness of grapefruit melds well with the slight woodiness of the maple syrup and the mellowness of the Bourbon. Easily my favourite Bourbon drink from my (limted experience). Uses WT101.