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!