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!

Porchside Pairing: H. Upmann 1844 Añejo with Old Elk Cigar Cut

Another evening of beautiful weather meant another sit on the porch. With no other plans, I dug into the humidor for something on the larger side and landed on the H. Upmann 1844 Añejo Toro. At 6 x 54, it promised a solid couple of hours of enjoyment.

The cigar wears a smooth, oily Ecuadorian Habano wrapper that shimmered in the fading sunlight. Construction was excellent — an even, seamless roll. Beneath the wrapper, a Pennsylvania Broadleaf binder holds filler tobaccos from the Dominican Republic, Honduras, and Nicaragua. This blend, aged for at least five years (as suggested by the name Añejo — Spanish for “old” or “vintage”), promises depth and complexity. Mine had been resting in the humidor about nine weeks, part of the June COTM shipment from Cigar and Pipes.

The smoke opens with rich notes of cocoa, coffee, and mild pepper spice, soon joined by hints of caramel sweetness and a sturdy woodiness. Cedar and pepper weave in and out throughout the long burn, but the profile stays balanced — complex yet approachable, with a satisfying full body. Construction was spot-on, delivering a steady burn and clouds of creamy smoke.

I was so caught up in the cigar that I nearly neglected the pour at my side: Old Elk Cigar Cut bourbon. Typically a celebratory pour for me, it felt right for this leisurely evening.

This bottling was the first “cigar blend” release from Old Elk Distillery in Fort Collins, Colorado. Built on six-year-old bourbons further finished in Sherry, Armagnac, Port, and Cognac casks, it’s bottled at 110.6 proof. On the nose, caramel, vanilla, toasted oak, and spiced fruit draw you in. The palate reveals layers of dark chocolate, toffee, and baking spice, with faint notes of tobacco and leather lingering in the long, warming finish.

Like the cigar, the bourbon is layered and complex. I’ve always found port- and sherry-finished bourbons to pair beautifully with cigars, and the additional cask influences here add even more depth. It remains one of my favorite pours to enjoy with a full-bodied smoke — though it has become increasingly elusive on shelves. Old Elk has also released a Cigar Cut Island Blend, but that one still eludes me.

What more could I ask for? A bold, flavorful cigar, an exceptional pour, the setting sun, and blues floating from the outdoor speaker. A perfect evening.

Cheers!

Elegance & Power: H. Upmann 180th Anniversary Meets Knob Creek Bourbon x Rye

I first smoked the H. Upmann 180th Anniversary Churchill back in May. The cigar impressed me then, and I suspected it would only improve with some rest in the humidor. After nine months of humidor rest, it was time to find out.

Released in July 2024, this limited edition celebrates 180 years of the H. Upmann legacy, a brand founded in 1844 by German banker Herman Upmann in Havana, Cuba. The Churchill is an elegant 7 x 50 cigar dressed in a chocolate-hued Nicaraguan medio tiempo wrapper — a rare leaf that appears on only about two percent of plants. Typically used sparingly in filler blends, medio tiempo is prized for its concentrated strength and flavor, making it a unique choice for a wrapper. The binder and fillers are also Nicaraguan, lending further depth and character.

From the first draw, the cigar opened with rich notes of chocolate and dark raisins, soon joined by a complex medley of black coffee, pepper, and cinnamon, underpinned by a creamy fruit sweetness. Full-bodied, flavorful, and refined, it proved worthy of the 180-year milestone it commemorates.

For the pairing, I reached for Knob Creek Bourbon x Rye Whiskey, bottled at 113 proof. Knowing this would be a long smoke, I wanted a spirit that could keep pace. Introduced in July 2024, this “Bourye” blend combines 30% 9-year-old Kentucky straight bourbon with 70% 7-year-old Kentucky straight rye. On the nose, rye spice and caramel sweetness greet you, while the palate leans rye-forward — bold pepper and cinnamon backed by brown sugar and dark fruit. I’ve enjoyed it neat before and find it a hearty pour on its own.

As the cigar progressed, I noticed the whiskey’s palate-coating spice was starting to overshadow some of the cigar’s subtle sweetness. A few drops of water changed the equation. After resting a moment, the whiskey softened, allowing more fruit and brown sugar to emerge — and that’s when the pairing truly clicked.

The H. Upmann 180th Anniversary Churchill delivered nearly two hours of steady, satisfying smoke with a flawless burn that needed no touch-ups. The extra time also left room for a second pour of the Knob Creek Bourbon x Rye, making for a thoroughly enjoyable evening.

Cheers!

H. Upmann 180th Anniversary Churchill Cigar Review – A Bold & Elegant Smoke

I’ve had several H. Upmann 180th Anniversary Limited Edition Churchill cigars resting in my humidor since last November. Released in July 2024, these cigars commemorate the 180-year legacy of the H. Upmann brand, founded in 1844 by German banker Herman Upmann in Havana, Cuba. I’ve been waiting for warmer weather to light one up — I didn’t want to risk a somewhat pricey cigar to cold temperatures or a rushed smoke.

The H. Upmann 180th Anniversary Limited Edition Churchill is an elegant 7 x 50 cigar. It features a chocolate-hued wrapper leaf, identified as rare Nicaraguan medio tiempo — a small, potent leaf that occasionally grows at the top of the tobacco plant. Harvested from only about two percent of plants, medio tiempo is prized for its rich flavor and concentrated strength, and is rarely used as a wrapper. The binder and fillers are also Nicaraguan, which adds to the cigar’s depth and character.

The cigar sports a striking primary band marking H. Upmann’s 180th year and an unusual, cap-like foot band covering the foot. While attempting to remove the foot band without tearing it, I accidentally cracked the wrapper at the foot. Thankfully, a quick touch-up with PerfecRepair resolved the issue. A straight cut at the cap delivered a smooth, open draw.

From the first puff, I knew this was going to be a flavorful and complex smoke. Even before it had a chance to fully warm up, it delivered rich notes of chocolate and dark raisins. Black coffee, pepper, and cinnamon soon followed. The bold, flavorful smoke was complex and full-bodied, yet never harsh. A layer of spiciness sat beneath the dark coffee and sweet, dark fruit flavors, adding complexity without overwhelming the palate.

I paired the cigar with a classic Negroni, as I often do when not drinking bourbon. The bitter, botanical drink pairs well with full-flavored cigars, especially robust Nicaraguan blends like this one.

The H. Upmann 180th Anniversary Limited Edition Churchill provided an hour and 50 minutes of rich, satisfying smoking pleasure. It’s likely as bold and complex as a cigar can get while remaining smooth and enjoyable. To say I enjoyed it would be an understatement. I held onto the tiny nub with my fingertips, trying to draw out the experience as long as possible. I’m already looking forward to lighting another from my stock — though it will definitely be saved for a special occasion.

Cheers!

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