Smoke and Spirit: La Madonna Negra and the Legacy of Uncle Nearest

I’ve enjoyed the Black Label Trading Co. La Madonna Negra numerous times over the past couple of years, and recently revisited one that had been resting in my humidor for nearly two years — left from my original pre-release order.

Cloaked in a rich U.S. Connecticut Broadleaf Maduro wrapper, the cigar features an Ecuadorian Habano binder and fillers from Nicaragua and Pennsylvania. It boasts a soft box press and is dressed with striking black, white, and gold-accented bands that contrast beautifully against the reddish-chocolate hue of the wrapper.

This well-aged stick burned evenly and delivered a medium- to full-bodied experience. Dark chocolate, espresso, and dark cherry took center stage, while subtle notes of black pepper and cedar added depth and complexity in the background.

That said, this particular cigar did present a tight draw initially. After a few minutes of struggling, I reached for the PerfecDraw tool and extracted a sizable stem that had clearly been restricting airflow. Once cleared, the draw opened up nicely, producing copious smoke and allowing the cigar’s full flavor profile to shine through.

As I enjoyed the La Madonna Negra, I reached for a nearly depleted bottle of Uncle Nearest 1856 Premium Whiskey — a bottle I realized I’ve somehow never written about in these Musings.

Uncle Nearest is a Tennessee distillery named in honor of Nathan “Nearest” Green, the formerly enslaved man who taught Jack Daniel the craft of distillation. The “1856” marks the earliest documented involvement of Nearest Green as the master distiller for the operation that would eventually become the Jack Daniel's Distillery

While technically not a bourbon due to Tennessee whiskey's legal classification requirements, Uncle Nearest 1856 is extremely close in profile. It undergoes the Lincoln County Process, which involves filtering the spirit through sugar maple charcoal before aging — an essential characteristic of Tennessee whiskey. In every other respect, it meets the legal standards of a bourbon. Whether Tennessee whiskey is bourbon remains a long-running (and mostly semantic) debate — one I’ll leave to others.

On the nose, the 1856 offers notes of vanilla, caramel, and toasted oak. The palate brings brown sugar, maple syrup, charred oak, and a touch of spice, all carried with a gentle heat from its 100-proof strength.

Compared to the Jack Daniel’s Old No. 7, the “classic” example of Tennessee whiskey, Uncle Nearest is richer, bolder, and more layered — closer to a classic bourbon than its softer Tennessee sibling. One reason my bottle’s nearly empty: I've found it makes a fine Old Fashioned and has often been in my rotation for that cocktail.

As for the pairing, La Madonna Negra was an ideal companion to the whiskey. The cigar’s dark chocolate and espresso notes harmonized with the whiskey’s vanilla and caramel, while the 100-proof backbone of the Uncle Nearest stood up well to the cigar’s bold character.

Cheers!