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Reinventing the Old Fashioned for Exceptional Cigar Pairings

Reinventing the Old Fashioned for Exceptional Cigar Pairings

It rarely comes up during the cigar events I participate in but I also have a background in mixology and when a finely crafted cocktail meets a well-aged cigar it is always a thing of beauty.

I find the art of pairing cocktails with cigars a truly rewarding experience. In this article I’m excited to share three versions of a classic cocktail, the Old Fashioned, these unique variations will beautifully complement your favorite cigar.

The Old Fashioned is a cocktail steeped in history, dating back to the early 1800s. It’s a testament to simplicity and balance, traditionally made with whiskey, sugar, water, and bitters. For those keen to try their hand at crafting this timeless drink at home, you’ll be pleased to know it doesn’t require fancy  equipment - a stirring glass, a bar spoon, and a strainer is all you’ll need.

“It’s the perfect example of the saying ‘Less is more,’” says Aubrey Slater, bartender at Honeybee’s in New York, about the Old Fashioned Cocktail.

“The Old-Fashioned was an evolution of the Whiskey Cocktail, which was simply whiskey, sugar, bitters, and water, and was served as early as 1800 or so,” explains cocktail authority Robert Simonson, author of The Old-Fashioned: The Story of the World’s First Classic Cocktail, with Recipes and Lore. “When bartenders in the 1870s and 1880s began adding embellishments to their Whiskey Cocktails, some customers rebelled against the innovations, preferring the traditional version and thus ordering “old-fashioned whiskey cocktails” instead. “That name was eventually shortened to Old-Fashioned.”

Now, let’s talk about the stirring method. Stirring a cocktail, unlike shaking, is about gently combining the ingredients, chilling them, while preserving the texture and clarity of the drink. To stir a cocktail, add your ingredients to a stirring glass filled with ice, then use a bar spoon to stir smoothly for about 20-30 seconds depending on how much dilution you want added to your drink.

I created a few variations of this drink which I often enjoy depending on the day and cigar I am having and here are 3 of the ones I most often make.

                       

1. Tobacco Old Fashioned:
This variant is a nod to the traditional cigar lover. Start with 2oz of a robust Bourbon – Woodford Reserve Double Oaked or Old Forester 1910 are excellent choices. Add in 2 dashes of simple syrup for a touch of sweetness, then 3-4 dashes of Tobacco Bitters (I used Fee Brothers Turkish Tobacco Bitters) for an added layer of complexity. This cocktail mirrors the rich, tobacco leaf tones of a cigar, making each sip a journey deeper into the heart of tobacco’s essence.
I pair this with a full bodied habano like the Bolivar Libertador.
Originally released as a French regional cigar with limited distribution, the Bolivar Libertador quickly gained a well-deserved regular release. It’s an aromatic delight for special occasions measuring at 164mm by a 54 ring gauge.

This is a pairing that will never disappoint since flavors go impeccably well together, tobacco, honey sweetness, cedar and oak, cinnamon spice…absolutely gorgeous

                        
2. Maple Old Fashioned:
A delightful pairing; this version is like a dessert in a glass. Use 2oz of a maple cask-aged Bourbon; I used  the Woodford Reserve Maple Wood Finish. It has rich and sweet hints of brown sugar, milk chocolate, and fresh toasted oak. Warmth of cinnamon spice and faint hints of maple syrup are also present. Finish is amazing with with delicate maple syrup notes lingering on. If you find this one pick up a bottle since this was released on 2010 only. You can also use Widow Jane Decadence Maple Syrup Barrel Finish - another gorgeous whiskey maple expression.
The addition of 2-3 dashes of Angostura Bitters and a teaspoon of Maple Syrup creates a harmonious blend of sweet and spicy. This cocktail’s sweetness complements the cigar’s spiciness, while the chocolate and toasted oak notes offer a delightful pairing experience with the tobacco’s natural flavors.
This is a more desert forward cocktail, it replaces a chocolate cake with pride and will not disappoint.

This is a desert worthy of a fantastic full bodied habano, something in the Prominentes vitola, also known as a Double Corona maybe?
The Bolívar Double Coronas Edición Regional Medio Oriente. A mighty 49ring x 194mm habano released in 2007. This was a spectacular pairing from beginning to end.

                        
3. The Rum and Coffee Old Fashioned:
This elegant and refined variation is for those special moments. Choose a high-quality rum, like the Havana Selection de Maestros, measuring 1 and ½ oz. Mix this with ½ oz of Mr. Black Cold Brew Coffee Liqueur and 2 dashes of Angostura Bitters. The rum’s rich, velvety texture combined with the coffee liqueur’s depth makes for a luxurious pairing with a full-bodied cigar. It’s a testament to how premium ingredients can elevate a cocktail to new heights, matching the sophistication of a well-crafted and aged cigar.

For this cocktail I chose a special cigar, I needed something with a lot of smoothness but with a big enough kick to keep up with the intense flavors of the cocktail. The Cohiba Behike 52 needs no introduction. Absolutely fantastic pairing. The coffee, the rum, the spices and the tobacco were absolutely amazing. The core flavors we all love in any cigar are very well expressed in this rich and delicate pairing.

​​Each of these cocktails brings something unique to the table, enhancing different aspects of a cigar’s profile. The Tobacco Old Fashioned emphasizes the robust, tobacco leaf tones of the cigar, creating a rich and immersive experience. The Maple Old Fashioned, with its sweet and spicy notes, offers a delightful experience. Finally, the Rum Old Fashioned, with its luxurious and deep flavors, complements the complexity and richness of a premium cigar, making each puff and sip a truly indulgent affair.

​​So, as you explore these pairings, remember it’s not just about the taste – it’s about the experience. Here’s to enjoying the finer things in life – cheers!