The Churchill That Made Me Feel Stupid

H. Upmann 180 Anniversary Churchill – Bury the Leaf

Sometimes the cigar that makes you feel stupid is the one you needed to smoke.

Not because it embarrassed you. Not because you couldn’t figure it out. Because somewhere along the way, you decided you already knew enough to leave it alone.

H. Upmann has been one of those brands for me.

The name lives in that old-world corner of the cigar universe where my brain immediately goes to Cuba, history, and something that doesn’t quite feel connected to the cigars sitting in an American humidor today. So while I’ve filled humidors with Rocky Patel, Oliva, My Father, and plenty of other familiar names, H. Upmann mostly watched from the sidelines.

Then an H. Upmann 180 Anniversary Churchill showed up in a Cigar Page Plus Mystery Flight.

And for $8.60 delivered to my door, it proceeded to make a pretty convincing argument that I’ve been doing this wrong.

This wasn’t merely a good cigar from a brand I’ve overlooked. It was one of those evenings when you eventually realize you’ve stopped reviewing the cigar and started simply enjoying the damn thing.

Maybe there’s something to this trying-new-things business after all.

By the Numbers

• Vitola: Churchill
• Wrapper: Nicaraguan
• Filler/Binder: Nicaraguan
• Cut: Colibri SV cut
• Procured from: Cigar Page — Page Plus Mystery Flight
• Price Paid: $8.60 shipped
• Estimated MSRP: Not established in session notes
• Duration: 1 hour, 26 minutes
• Band Rating: 4 Bands — Box Worthy

Construction & First Impressions

Let’s start with the obvious: a Churchill just looks distinguished.

My preferred vitola is generally the Toro, and I’ve never really given the Churchill much attention. Maybe I subconsciously associated the extra length with an unnecessary time commitment. Which makes very little sense considering I’ve never had a problem picking up a 6×60 and disappearing into the lounge for a while.

But put a Churchill in your hand and suddenly you feel like you ought to have an opinion on foreign policy.

The 180 Anniversary looked the part.

The wrapper had an unusual texture that immediately reminded me of velvet. Not particularly oily, but soft-looking and tactile, with plenty of visible veins and some pronounced seams. The cap work was solid, and the cigar felt well constructed from the start.

Then there’s the presentation.

Around the foot was an additional band that effectively enclosed it, creating the appearance of a closed foot without actually using wrapper leaf to do it. It’s unnecessary. It’s decorative. It’s exactly the sort of little touch that can become gimmicky when the cigar underneath it doesn’t deliver.

Fortunately, that wouldn’t become a problem.

The wrapper and foot offered sweet tobacco and cocoa, while the cold draw moved firmly toward milk chocolate. The Colibri SV made easy work of the cap, although it also produced a small wrapper crack — something I’ve encountered with that cutter before. Nothing looked serious enough to derail the evening.

Once lit, the first aroma immediately abandoned the sweetness of the cold draw. What came off the cigar instead reminded me of fresh topsoil: earthy, dark, unmistakably cigar-like and surprisingly inviting.

That earthiness became the foundation almost immediately, with chocolate hanging somewhere behind it and pepper beginning to make its presence known.

And then this cigar got weird.

In the best possible way.

First Third

Follow me here.

Imagine a desert rose dipped in honey.

I have no idea whether growing roses in the desert is practical, and I don’t recommend dipping perfectly good flowers in honey. But that was the picture this cigar painted.

There was a dry quality to the smoke accompanied by enough sweetness to soften it, then a subtle floral note underneath everything. Pepper followed close behind, keeping the profile grounded rather than allowing the sweetness to take over.

It was unusual as hell.

It was also delicious.

The smoke production was fantastic from the beginning, and the burn settled in beautifully. This cigar had spent a little over a month acclimating in the humidor, and it seemed perfectly content with the arrangement.

A restricted exhale brought a little grass into the picture, which made sense alongside all that earth. There was also a sweetness that kept threatening to break through without ever completely taking control.

Then came another oddball combination: berry and mixed nuts.

Raspberry or blueberry came to mind alongside something closer to cashew and peanut. I’m well aware that sounds like somebody dumped trail mix into a fruit bowl, but my palate is my palate, not the palate. Around here, if something weird shows up, we’re calling it out.

As the first third developed, the profile became creamier. Buttery leather and spice joined the earthiness, and everything started settling into place.

At that point, I had to admit something.

This cigar was exposing a bad habit.

I tend to find something I like and ride that horse until the poor bastard needs medical attention. Find a Rocky Patel I enjoy? Suddenly there’s a humidor full of Rocky Patel. Discover another Oliva? Better make room. My Father earns my attention? Apparently we need those by the box now.

There’s nothing wrong with keeping favorites around. That’s the whole point of finding favorites.

But there’s a difference between having staples and building walls around your palate.

The H. Upmann 180 Anniversary was making a pretty compelling case for knocking a few of mine down.

Second Third

The sweetness eventually packed its bags.

If that milk chocolate from the cold draw ever truly arrived, it basically got its passport stamped, looked around the country, and got the hell back out.

The desert rose disappeared with it.

What replaced them was an entirely different animal: wood, earth, leather and pepper. The cigar went from unusual and slightly delicate to something considerably more rugged.

Downright manly is probably the easiest way to put it.

Mixed nuts returned underneath the heavier flavors, and a little coffee joined them. Nothing needed to dominate. The blend simply kept changing gears without grinding them.

The wood became increasingly prominent as the cigar progressed, while the leather began backing away. Spice remained underneath everything rather than punching through it.

Meanwhile, the construction was giving me essentially nothing to complain about.

The smoke output remained impressive. The ash held well and dropped naturally. The draw behaved. The burn behaved. The wrapper kept that same velvet-like appearance and texture it had before lighting.

For a cigar carrying anniversary branding and special presentation, that’s important.

Fancy bands can get you through the front door. They can’t keep you at the party.

The 180 Anniversary was earning its stay.

More importantly, the Churchill format wasn’t becoming the marathon I’d apparently convinced myself it would be. The cigar was long, sure, but the experience never felt long. There’s a meaningful difference between the two.

When you’re watching the clock, the cigar has probably already lost.

I wasn’t watching anything but the smoke.

Final Third

Eventually the wood stopped sharing custody.

Oak took the cigar.

Not cedar. Not that brighter, sometimes almost mineral character I can occasionally mistake for something metallic.

Oak.

The kind of oak that makes brisket great.

It wasn’t overpowering, but it was strong enough to command the room. The earth remained underneath it, and a restrained spice continued working in the background, but the oak had become the identity of the final third.

If acorns had started falling from the ceiling of The Evening Draw Lounge, I probably would have just accepted that as part of the experience.

Hell, if I were a squirrel, this is apparently the portion of everybody’s discarded cigars I’d be collecting.

That’s a terrible analogy.

We’re keeping it.

The only meaningful construction issue of the entire smoke appeared here when part of the wrapper began lagging behind the burn. Even then, it wasn’t dramatic. I gave the cigar a chance to sit rather than immediately attacking it with the lighter, and physics handled most of the problem without petroleum.

That’s a win.

The ash remained respectable, smoke production stayed strong, and that velvety wrapper maintained its character nearly all the way down.

By this point the cigar had also made its larger point.

Presentation matters when the cigar can back it up.

The 180 Anniversary arrives dressed like an occasion. The ornate anniversary band and unusual foot treatment tell you before the first cut that somebody intends this to feel different.

Sometimes that’s where the experience ends.

Here, it was just the introduction.

Millennium of Aftermath

I spent a long time treating H. Upmann like a name I already understood without actually giving the cigars enough opportunity to explain themselves.

That’s on me.

The 180 Anniversary Churchill didn’t just give me a reason to revisit H. Upmann. It reminded me why blindly stacking familiar cigars can eventually become its own kind of rut.

I know what I like.

That’s useful right up until it keeps me from finding something else I like.

This cigar came from a mystery sampler. Left entirely to my own habits, there’s a good chance I would have spent the same evening reaching for a My Father Le Bijou 1922, a Rocky Patel Edge Habano, or another familiar resident of the humidor.

Instead, I got honeyed floral weirdness, berries and nuts, buttery leather, earth, pepper, coffee and eventually enough oak to start attracting woodland creatures.

That’s a hell of a trade.

It also reinforced why samplers, cigar-of-the-month programs and good brick-and-mortar lounges still have a place even when online cigar shopping makes it dangerously easy to buy exactly what you already know.

Ask somebody what you’re missing.

Buy two or three cigars you’ve never smoked instead of another ten you already have.

Let the humidor have a few question marks in it.

Because every once in a while, one of those question marks turns into this.

The H. Upmann 180 Anniversary Churchill delivered excellent construction, substantial smoke production and a flavor progression that genuinely evolved from beginning to end. More importantly, the experience never felt like the investment its Churchill dimensions suggested.

I paid $8.60 shipped.

At that price, this isn’t even a conversation.

The harder question is what happens when you find it closer to full retail, and based on this experience, I’m still interested.

Five Bands remain reserved for the cigars that force me to start stacking replacements. One cigar isn’t enough to cross that line.

But this one came knocking.

4 Bands — Box Worthy.

H. Upmann spent plenty of time sitting outside my regular rotation.

The 180 Anniversary just opened the door.