I was recently reacquainted with the concept of rum-running while reading Mallory O’Meara’s excellent book Girly Drinks. The book details women’s significant contributions to the history of alcohol. One of the most memorable figures in the book is Gertrude “Cleo” Lythgoe, who smuggled spirits (mostly whiskey) into the United States via the Bahamas during Prohibition. Rum-running was a huge business during Prohibition, and Lythgoe was one of the key players in a network that kept the American drinking public supplied with top-shelf booze.
The history of this drink, like many, is difficult to verify. According to some accounts, it was created by a bartender in the Florida Keys in the 1970s as a tribute to the people who kept America wet during Prohibition. At first glance it might look like a gruesome hodgepodge of ingredients, but I liken this drink to a fruitier rum version of a Singapore Sling—perhaps a bit overstuffed, but certainly more than the sum of its parts, which is a key attribute of all great drinks.
Some recipes call for light and dark rum, but I’ve simplified things a bit and just gone with dark for this rendition. If you happen to have another dark berry liqueur on hand, like crème de cassis or Chambord, feel free to use that in place of the blackberry liqueur if you don’t feel like adding another bottle to your home bar. And for the pineapple juice and grenadine: Store-bought is fine if you must, but making your own adds a delicious shine.
—John deBary
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