Rob Roy Cocktail and the Bartender who created it

The Rob Roy cocktail is a true classic. It is essentially a Manhattan with Scotch substituted for North American Whiskey.

The drink benefitted from Scottish whisky becoming widely available for the first time in 1890 North America.

Fun fact, in 1898 the first commercial ever shown before a motion picture was an advert for Dewar’s Scotch.

Rob Roy was a real historical character, but the name of the drink is a reference to a popular operetta. Opening in New York, October of 1894, the hit play’s name of Rob Roy served as inspiration for the cocktail because of the obvious reddish color of the drink and use of Scotch.

Frank Caiafa, Beverage Manager of the modern Waldorf Astoria, notes that Herald Square hosted the operetta. Herald Square was very close to the original Waldorf. It stands to reason they’d have wanted to create association with their bar.

Naming cocktails after popular plays and films was common practice. The Trilby, Blood And Sand and Tom And Jerry cocktails all support this trend.

There are three common ways to serve a Rob Roy. The standard is with sweet vermouth and doesn’t need specified when ordering. “Dry” calls for dry vermouth and “Perfect” is when you do a mixture of sweet and dry vermouth. Angostura Bitters were the standard in the Rob Roy and today we have much room for experimentation.

Creator of the classic Aviation Cocktail, Hugo R. Ensslin offered a “perfect” Rob Roy variation while working at New York’s Hotel Wallick. In his book, “Recipes for Mixed Drinks” (1916), Ensslin called the Rob Roy variation The Affinity.

Most publications say that the creator of the Rob Roy cocktail is lost to history. That is partly due to Prohibition.

One of the last Barmen at the Waldorf Astoria Hotel before Prohibition was Joseph “Dan the Barboy” Taylor (1894-1920). Albert Stevens Crockett wrote a book called, Old Waldorf Bar Days”  (1931). Based on the “Dan the Barboy” diary of the bars history and included many recipes copied in shorthand. Sadly, by the early 1930’s so much bar knowledge had been lost that many people could barely understand the recipes, mystified by the ingredients and styles recorded. Crockett himself was unfamiliar with most of the recipes and ingredients Taylor gave him. Much less able to fully credit bartenders for their creations. Crockett stated that the recipes were “decoded, rearranged and more or less classified” but also admitted he understood little about cocktails. The original bar diary by Taylor was lost to history.

One of the most glaring mistakes in Crockett’s book is that he calls for Gin instead of Gum (Simple) Syrup in many Waldorf Bar recipes.

Johnnie Solon was another very noted Waldorf Bartender, he started working at the Hotel in 1899. Credited by Crockett as being the inventor of the Bronx Cocktail. But then there’s this…

Bronx Cocktail, Rob Roy Cocktail, John "Curley" O'Connor
“The Virginia Enterprise”. February 15, 1901 credits John “Curley” O’Connor as creator of The Bronx Cocktail.

So who invented the Rob Roy Cocktail?

John "Curley" O'Connor, Rob Roy

In the late 1890’s the Bronx cocktail appeared on Waldorf menus attributed to John “Curley” O’Connor. Bartending at the Waldorf from 1893, John “Curley” O’Connor likely created one of the most popular drinks of all time. It stands to reason he could have easily done it twice, inventing the Rob Roy Cocktail. There were other bartenders at the Waldorf then, but none of them did anything notable beyond a record of employment in the Waldorf Archive. (Paddie ‘Patsy’ Hafer, Billie Lahiff, Frank MacAloon, Mike O’Connor)

John “Curley” O’Connor continued as a bartender until late in life, eventually setting up shop in Miami in the 1940’s.

John "Curley" O'Connor, Rob Roy Cocktail
John “Curley” O’Connor bartending in 1941, aged 70

Rob Roy Cocktail recipe:

Rob Roy Cocktail, John "Curley" O'Connor, Classic Drinks with Three Ingredients

1.5 parts Compass Box Blended Whisky of choice
1 part Fine Vermouth 
3 dashes Bitters 
Stir with ice and strain into chilled coupé. Express lemon oil over drink and garnish with lemon peel twist.

We got the rare opportunity to play with Compass Box “The General”, which’s named for Buster Keaton’s classic 1926 film. Too perfect for the purpose of honoring a drink named after a play. There were only 1668 bottles produced of this amazing blend. At a cask strength of 53.4% it is both wonderfully reminiscent of a fine XO cognac in flavor and mouthfeel yet boldly spicy as any over-proof whisky.

We loved hearing that Compass Box produce with cocktails in mind and are non-chill filtered without any caramel coloring. For the Vermouth, the quality and bite of Cocchi Americano was enticing. Dillons Bitters ESB add aromatic cherry notes, with overtones of vanilla, cloves, allspice, and cassia bark. The balance and complexity of the Rob Roy will make any fan of spirit forward cocktails want to try it again and again with every Scotch in their collection.

Thank you to David Wondrich, Waldorf Archivist Erin Allsop and Waldorf Astoria Beverage Manager Frank Caiafa for their help in researching this piece.

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