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!

A Summer Sobremesa: Wine, Smoke, and Setting Sun

After a hearty steak dinner accompanied by a good bottle of wine, we moved out to the deck to continue the evening under the open sky. As I perused the humidor in search of a fitting cigar to round out the experience, I selected the Sobremesa Solita Toro — a standout offering from Dunbarton Tobacco & Trust. It had been resting in the humidor for two months so was well-primed for lighting up.

The name Sobremesa — Spanish for “upon the table” — refers to the cherished Latin tradition of lingering at the table after a meal, enjoying conversation and company. Though we’d shifted from the dining room to the deck, the sentiment carried through.

The Solita Toro is a well-constructed 6 x 52 cigar, dressed in a smooth Ecuadorian Habano wrapper that takes on a reddish hue in the evening sun. Beneath the surface lies a binder of Mexican San Andrés Negro and a filler blend of Nicaraguan and Pennsylvania Broadleaf ligero. The presentation is understated, adorned only with two simple gold bands.

My cigar had a slightly snug draw — tighter than I usually prefer — but not enough to warrant any correction. The burn was slow and even, delivering an ample, satisfying volume of smoke.

Medium-bodied in profile, the Solita offered a rich mix of cedar, cocoa, and coffee as core flavors. A gentle hint of pepper emerged on the retrohale, and the finish settled into a creamy sweetness. The cigar’s balance and nuance encouraged slow, thoughtful draws and a lingering exhale to fully savor its complexity. 

It burned evenly and cool for a long, relaxing 1 hour and 40 minutes — an ideal companion to an unhurried evening.

The wine of the night was Videre from Wilderness Run Vineyards — a 50/50 blend of Merlot and Malbec. Both varietals are personal favorites when pairing wine with food, and this blend hit a pleasing middle ground. Medium-bodied, it brought the bold, dark fruit notes characteristic of Malbec, while Merlot softened the tannins and softened the finish. The wine’s fruit-forward profile paired beautifully with the cigar’s creamy finish, creating a complementary interplay of flavors.

As the sun dipped below the trees and the temperature cooled ever so slightly, birdsong filled the air — an idyllic soundtrack to our “sobremesa.” It was a perfect way to end a meal and enjoyed the shared relaxation.

Cheers!

Five O'Clock Friday: Travel Provisions

Entering the weekend well prepared. 

Looks like an Italian First-Aid kit.

Cheers!

Action Item From Cigar Rights of America

Attacks on the premium cigar industry seem relentless. Fortunately, the Cigar Rights of America (CRA) stands as the first and only consumer-based public advocacy group dedicated to protecting your right to enjoy premium, hand-rolled cigars. Their efforts have been instrumental in pushing back against the bureaucratic overreach of the FDA.

Now, the CRA is urging all cigar enthusiasts to support H.R. 2111 — the CIGAR Act, which seeks to exempt premium cigars from FDA regulation. Your voice matters in this fight for cigar freedom.

Why H.R. 2111 Matters:

Congressman Byron Donalds (R-FL), joined by a bipartisan group of lawmakers, has introduced H.R. 2111 – the CIGAR Act. This commonsense legislation would establish a clear exemption for premium cigars from FDA regulation, ensuring they are treated distinctly from mass-market tobacco products and protected from future regulatory overreach.

Why H.R. 2111 Matters:

✅ Protects Consumer Choice: Premium cigars are handcrafted products, enjoyed occasionally by informed adults. H.R. 2111 puts in place protections that ensures they’re not swept up in regulations meant for entirely different products.

✅ Prevents Future Overreach: While a federal court vacated FDA authority over premium cigars, that protection isn’t permanent. This bill codifies a clear definition and exemption into law, guarding against future regulatory reversal and preventing FDA from regulating premium cigars again.

✅ Supports Small Businesses: Family-owned manufacturers and specialty retailers face crushing compliance costs under FDA regulation. H.R. 2111 shields them from red tape that threatens their survival.

Take action now! Contact your representatives in Washington today, and tell them to support H.R. 2111 and stand up for common sense protections for premium cigars!

Take a few minutes to contact your representatives in Washington with this convenient form and urge their support of H.R. 2111.

Sign the CRA petition in support of H.R. 2111

Cheers!

Joya de Nicaragua Cuatro Cinco and a Perplexing Angel's Envy Triple Oak

I was pleasantly surprised to see the Joya de Nicaragua Cuatro Cinco Toro included in the April Luxury Cigar Club package. This was a cigar I had not smoked in several years, but one I had enjoyed frequently in the past. After letting this one rest for a couple of months, I finally lit it up on a warm evening.

The Cuatro Cinco is an impressive-looking cigar. This 6¼ x 50 Toro is wrapped in a dark, oily Nicaraguan Habano leaf from the Jalapa Valley. Both the binder and filler are also Nicaraguan, including some 5-year-aged ligero that’s been finished in oak barrels. Even the band — black, white, and gold — adds boldness to the presentation.

The cigar was originally released to commemorate the 45th anniversary of Joya de Nicaragua. A closer look at the band reveals clever design details: the “a” in Cuatro is shaped like an upside-down 4, and the second “C” in Cinco mirrors a flipped 5. Cuatro Cinco translates literally to “four five.”

It opens squarely in the medium-bodied range, gradually edging toward full-bodied strength by the halfway mark. This is a rich, complex smoke, with flavors of dark chocolate, espresso, nuts, and cedar, accompanied by a moderate spice of pepper and cedar. The finish is fairly short, but a fleeting, creamy sweetness emerges on the back end.

The draw was initially tighter than I prefer, but a quick adjustment with the PerfecDraw tool cleared out an obstructing stem. From then on, the draw was spot on, and smoke production was plentiful. The Joya de Nicaragua Cuatro Cinco is a flavorful, satisfying cigar I’ve enjoyed on multiple occasions — and this one was no exception.

The go along with the smoke, I decided to revisit the Angel's Envy Triple Oak Bourbon. Released in late 2024, the bourbon undergoes a unique finishing process. After first aging in the standard new American white oak barrels, the aged bourbon is portioned to undergo secondary finishing in three different oak casks: 20% in French Oak for at least three months, 40% in Chinkapin Oak for at least six months, and 40% in Hungarian Oak for six or more months. The “triple oak” mix is then blended for bottling at 92 proof.

My impressions of this bourbon have been mixed. On the nose, it’s fruity and slightly sweet, with little hint of the oak-forward profile to follow. On the palate, dry, raw oak dominates. There are notes of dark fruit, brown sugar, and spice, but they’re often overshadowed by the bourbon’s woody core.

I’ve returned to the Triple Oak several times and still haven’t quite figured it out. It’s not unpleasant — just different. It lacks the sweet, fruit-forward character typical of many bourbons. Curiously, during a previous tasting, I noted more sweetness and better balance than I did this time around. I’m well aware that cigars, food, and even mood can significantly influence flavor perception. I now suspect this bourbon might actually shine in a cocktail, where its oakiness could be tempered and complemented by other ingredients.

Despite my ambivalence toward the bourbon, the pairing made for an enjoyable and flavorful experience. The Joya de Nicaragua Cuatro Cinco remains a standout cigar, one I return to with confidence. Unlike the bourbon, there’s no question in my mind about the quality and depth of the smoking experience it delivers.

Cheers!

Aperol Spritz & the Liga Undercrown Shade: A Summer Pairing

They call it a “heat dome.” I call it summer in Virginia. With the afternoon sun ablaze and humidity thick in the air, bourbon — my usual standby — took a backseat to something lighter and more refreshing: the Aperol Spritz. It was Sunday leisure time, and the mood called for something bubbly, herbal, and slightly bitter.

Choosing a cigar to match the drink and mood was a bit more challenging. I wanted something on the milder side — which, frankly, isn’t a strength of my humidor. After a quick scan, I settled on the Liga Undercrown Connecticut Shade Gran Toro, figuring it was about as close to “mild” as I’d get.

This 6 x 52 Toro wears a pale Ecuadorian Connecticut Shade wrapper over a Sumatra binder, with Dominican Criollo, Nicaragua Criollo and Corojo fillers. Despite its delicate appearance, the cigar was beautifully rolled and had been resting for about nine weeks.

It began with more flavor than I expected — creamy coffee, sweet nuts, and a gentle pepper tingle. I’d peg it as mild-to-medium in body at first, though as it progressed, the coffee deepened into something darker, and the pepper picked up a bit more punch. A touch of citrus zest and sweetness lingered in the background, adding complexity. By the final third, it was firmly in medium-bodied territory.

Some salty potato chips with olive and cream cheese dip rounded out the aperitivo. While the Undercrown Shade isn’t a cigar I reach for often, it paired nicely with the refreshing spritz. Still, if I’m being honest, I prefer something bolder alongside Aperol’s bittersweet character — even if I’m not enjoying it on a cobblestone patio in Italy.

Cheers!

Summer Solstice: A Smoke, a Beer, and Spicy Shrimp

While running errands on June 20 — the Summer Solstice — conversations everywhere seemed to center on the approaching heat wave. Like clockwork, the first truly warm days of the year shift everyone’s focus to “keeping cool.” My usual response is something along the lines of, “Well, it is summer… in Virginia.” I typically follow up with a contrarian remark about my dislike of cold weather.

To mark the glorious end of chilly days, I enjoyed lunch out on the sunny deck. A plate of steamed shrimp and a cold beer made for a delightful Friday afternoon meal. It was warm, yes, but hardly oppressive. I’ll admit the black arms of my chair were scorching from the sun, and when I tried to read a bit on my phone, I was greeted with an alert: iPhone needs to cool down before you can use it. Even my phone was joining the chorus of complaints about the heat.

After finishing my meal, I grabbed another beer from the fridge and selected a cigar from the humidor. Back in my seat, I lit up and continued soaking in the warmth.

I had chosen the Foundation Aksum — a cigar I often reach for when I want something smaller and quicker. This 5 x 50 Robusto is wrapped in a dark Ecuadorian Sumatra leaf, with a Connecticut Broadleaf binder and Nicaraguan fillers from the Jalapa and Estelí regions. 

The Aksum offers a bold smoking experience, led by rich notes of sweet espresso and dark chocolate. Hints of black pepper, dark cherry, and raisin make their way in as well, all tied together by a lingering spicy finish. It paired beautifully with the hoppy Sierra Nevada Pale Ale — a fitting dessert after a spicy meal.

Eventually, I moved to the covered screen porch to get out of the direct sun. There, I finished my beer and cigar while enjoying a bit of reading in the breeze from the fans — a most relaxing afternoon.

Cheers!

Five O'Clock Friday: Live Wisely

Life is full of decisions. Make the right ones.

Enjoy the weekend.

Cheers!