This was invented by one Lucian C. Sprague, president of the Minneapolis and St. Louis Railway back in presumably the 1940s and into the 1950s, as the drink first appears in Ted Saucier’s 1951 Bottoms Up. I thought this one would be pretty tasty, but as I was making it, I began to think, “Hmmm…not a lot of sweetener in here, but a lot of lemon juice…uh-oh.”
1 jigger (1.5 oz) bourbon
1 jigger applejack or apple brandy
1 dash Angostura bitters
1 barspoon (1/2 tsp.) Cointreau
The juice of half a lemon
(I added one tsp. of rich simple syrup – see below)
Shake with ice and strain into an old-fashioned glass over cracked ice (or a huge ice cube, as I did). Garnish with a twist of orange peel.
My fears were not unfounded. This was about the sourest drink I’ve ever tasted. It was in fact undrinkable. I added a teaspoon of rich simple syrup, and that did the trick, although it was still a tad sour. Stirring in the syrup afterward was not as effective as shaking it in would have been, so I think this would be even better if you put the sweetener in with everything else right off the bat. The rye and apple brandy blend well together, and the orange peel and Cointreau add a nice hint of orange. In fact, this might be even better with just a few dashes of lemon juice instead of the half a lemon’s worth. In any case, with the simple syrup, four livers.