Pairing The Banker Annuity with Chattanooga Single Barrel

I had the cigar I wanted to smoke in hand — the H. Upmann The Banker Annuity. I knew it to be a medium-bodied smoke, perhaps even leaning even a bit milder. Scanning the whiskies on the shelf, I was torn. I was in the mood for a higher proof pour but didn’t want to overwhelm the cigar. I settled on the Chattanooga Whiskey Single Barrel Bourbon. Despite its 121.2 proof, I recalled it drinking on the milder side.

H. Upmann positions The Banker as a tribute to the brand’s founders — the Upmann brothers, German bankers who produced a special Cuban cigar in the 1800s for their most important clients. The modern line carries that inspiration forward.

The Annuity vitola is a 6″ × 52 with an Ecuadorian Habano wrapper, a Nicaraguan binder, and aged Dominican and Nicaraguan fillers. This stick had been resting in my humidor for nine weeks.

Chattanooga's Single Barrel is a “High Malt” bourbon made as part of the distillery’s single barrel and experimental programs. The mash bills feature at least 25% specialty malted grains, supplementing corn with malted barley and other malts. This particular barrel, B091, incorporates Yellow Corn, Malted Rye, Caramel Malted Barley, and Honey Malted Barley, and was aged at least four years.

Going into the pairing, The H. Upmann landed firmly at a low-medium body with cedar, almond, pepper, and coffee forming the core profile. A touch of sweetness developed late. The burn was wavy and required several touch-ups, though the ash itself held well.

The Chattanooga Single Barrel delivered dessert-like flavors — caramel, honey, citrus, and a hint of char. The finish was sweet and bready, capped with a bit more heat than ideal for the cigar. A few drops of water helped bring forward the fruit and soften the finish, creating a more harmonious combination.

As I settled into the smoke and sip, I enjoyed the shared dessert tones of the pairing, even if it didn’t quite rise to the level of exceptional. I did pour a little more whiskey as the 90-minute session continued, and despite the burn issues, the cigar stayed cool and enjoyable down to a finger-warming nub. In the end, the two may not have been a perfect match, but they proved satisfying companions — a pairing that came together even better than I first expected.

Cheers!