I think Drew Estate’s Undercrown is the cigar I’ve burnt the most of, in my life. Seriously. I’d guess that over the last five years or so I’ve gone through maybe… six boxes of these in total. That’s across almost every size – I’ve gone from Gran Toro, to the Gordito, to the Corona Viva, to the Corona Doble, and back to the Gran Toro over the years. Now six boxes might not seem like a lot for those guys out there who consistently buy the same box month in and month out. But that’s never been me, I’ve always been one to jump around from brand to brand. 

All that being said, Undercrown is a cigar I’ve always returned to, always recommended, and always enjoyed. Today, I want to explain why.

Before we jump into all that, I want to explain the background of the “Undercrown” for those who don’t know. Let’s jump back in time seven or eight years. It’s 2010 — the iPhone 4 was just released, Bing and Yahoo have decided to combine search tech to try to take down Google (spoiler alert: it doesn’t work), Drew Brees is the MVP of the Super Bowl after whipping the Colts, and a little cigar company known for their infused blends is killing the game with a cigar called “Liga Privada No. 9”. Now Liga Privada gets a lot of its success from the high-quality leaves contained inside it — the maduro wrapper is fermented extra-slowly and longer than most, and only the highest-quality filler leaves make their way into the final product. The rarity of the tobacco had a lot to do with the unique flavor, and the reviews were good. In fact, this hype surrounding this cigar was SO good, Drew Estate couldn’t keep up with production. 

So the decision comes down from the Drew Estate higher-ups: cigar rollers, “torcedores”, can no longer enjoy the Liga Privadas they roll while they’re rolling them. They need to light up something else. And, as the story goes, a few of these torcedores went on to combine alternate vintages and primings of the same leaves as the Liga 9 into a cigar of their own. After enjoying a few of these cigars themselves, the Drew Estate team realized they had something special here. A cigar crafted by the people, for the people — and so, Undercrown was born. 

Now don’t get confused. Just because this cigar was blended with “leftover” tobacco from the LP9 doesn’t mean it isn’t a premium experience. Take, for example, the Mexican San Andres maduro wrapper. On a lesser cigar, this wrapper leaf is gritty and rustic. On Undercrown, it’s oily, expertly applied, and nearly seamless. Underneath, you’ll find a Connecticut River Valley Stalk Cut and Cured Sun Grown Habano binder and a mixture of handpicked Brazilian Mata Fina and Nicaraguan Habano long-fillers. In each cigar, these tobaccos are rolled perfectly, with a great weight in the hand and an equal firmness all the way up the length of the 6” x 52 Toro. In (literally) over 100 of these cigars I’ve enjoyed, I’d be hard pressed to think of one with bad construction. 

Toasting the foot of this cigar and taking a couple draws you’ll find a full-flavor, with tons of production off each puff. The flavor is surprisingly creamy, for a cigar this dark. There’s a natural sweetness here, complemented by notes of woodsy flavor and vanilla (or “oak”, some would call it). While there’s a lot going on here, the cigar never inches all the way up the strength dial, resting just below what I’d call full-bodied. As it continues, coffee and black pepper join the mix, until, by the end, the sweetness is mostly gone and what’s left is a more typical Nicaraguan maduro experience — plenty of spice and earth. 

So why do I keep coming back to Undercrown? It’s consistent, it’s reliable, and it is, to me, a shining example of what a maduro cigar should taste like. Never overpowering, never disappointing, and never one-dimensional. If you haven’t tried Undercrown yet, grab a 5-pack of the Gran Toro or the Corona Viva size and give it a whirl. As a note, the Corona Viva contains a higher-ratio of ligero than the other sizes, so it’ll give you more of a spicy kick. And if you have enjoyed Undercrown before this, maybe it’s time to revisit this classic cigar. I guarantee you’re going to be happy you did.