Best Churchill Cigars To Try in 2021

A spirit like Sir Winston’s is greatly missed in trying times. We definitely wish he were here to take a big bite out of the ass out of all the problems we face. Unfortunately, he’s unavailable. We’re going to have to find a substitute, and in the meanwhile, we can keep our morale up with some of the best and highest-rated Churchill cigars around.

You can use these Churchills for relaxing, but if you really want to honor Winston’s memory and follow his example, you’ll puff away on one while working and gnaw on the damn thing when it goes out. Save your corner of the world, even if it’s only the size of your own home, from whatever rampaging animals are threatening it. It’s what Churchill would have wanted.

Montecristo Platinum Series Churchill Cigar – What’s in a Name?

Let’s kick this list off with perhaps the best Churchill of 2021, the Montecristo Platinum Series Churchill cigar. For those who have heard the Montecristo name, it’s important to note that the company has two branches. One brand operates out of the Dominican Republic, while the other is still made in Cuba. This 7x50 Platinum Churchill comes from the Dominican branch of Montecristo. As you can see by the 94-point rating, of course, the quality is still outstanding.

This cigar features a three-country filler blend of tobaccos from the Dominican Republic, Nicaragua, and Peru, so we’re getting a lot of variety in it. Strong international collaboration is something Churchill the man could certainly get behind, right? The binder holding this blend together is also Dominican tobacco, but the finisher is special – it’s a Mexican-grown habano-seed wrapper. This is how you know you’re going to get that spice that so many of us love!

The reviewers at Cigar Aficionado who blessed this smoke with its impressive rating raved about the fruitiness of it. Not bright citrus, but rather dense raisin, black cherry, and plum. They also noted a woody core of earth and hickory. To finish things off, you can’t miss the little pepper touch – a little spank on the tongue from the San Andrés valley.

Churchill fans will be fully satisfied.

Black Label Trading Co. Lawless Churchill Cigar – An Underdog with a Surprising Bite

The Black Label cigar brand has been around since 2013, but still feels like a boutique blender in how they approach many things. It’s under the umbrella of the Oveja Negra (“black sheep”) company run by James and Angela Brown in Estelí, Nicaragua. Aside from killer cigar art, the company makes some outstanding blends. This year, the Lawless Churchill is definitely turning some lighters in their direction.

With 93 points from the tastemakers at Cigar Aficionado, this 7x48 cigar is long enough to keep you busy puffing without being so fat that you’re held down for the count. It delivers medium-ish strength, and rewards smokers with a palate of chocolate, leather, and roasted (of course) peanuts. The binder and filler comes from soil not far from the Oveja Negra factory in Nicaragua, but the wrapper is what elevates this Churchill cigar into the best of 2021 category. It’s reddish brown Ecuadoran habano rosado tobacco, and it’s as pretty as it is tasty.

We’re definitely continuing to keep our eye on Oveja brands like Black Label, Emilio, and Dissident. The funny thing is, James isn’t in any hurry to take over the game. He describes himself as “a regular guy who has a love for tobacco and a passion for the process of cigar making.” The climb and grind continues – but like all great artisans, the team at Black Label is making it all feel like a natural ride down a countryside road through the tobacco farms.

Thanks for the delicious Churchill, folks.

La Aroma de Cuba Mi Amor Churchill Cigar – Still Amazing After All These Years

Having one of the absolute best cigar brands in the world in My Father isn’t enough for José "Pepin" Garcia. He’s got to put out these stealth blends under the Aroma de Cuba brand, too. Well, we’re on to you Don Pepin! You can’t hide your tasty blends from us – we know that masterful balance any time we smoke it, and we can trace it right to you.

This time, we’re savoring a 93-rated Churchill cigar that’s totally satisfying at 50x7 with medium-full strength. It’s actually got quite an array of flavors, all in a delicate mix where nothing seems out of place. That’s the signature of Don Pepin, to us – that subtle blending where it just seems like there’s the right amount of each flavor note. In the Mi Amor Churchill, we’re treated to a dessert smoke featuring cocoa, coffee, and caramel – then we’re sent to the next level by a tastefully spicy finish.

The filler and binder is Nicaraguan tobacco, which is wrapped in a Mexican habano leaf. Don’t sleep on this one, though. It’s been charting for almost a decade (it was Cigar Aficionado’s #2 cigar of 2011), and is still smoking up better than 90% of the cigars out there.

A Churchill cigar for the ages, no doubt.

H. Upmann 175th Anniversary Churchill Cigar – AJ Fernandez + Rare Leaf = Primo Smoke

Goodness gracious. Winston himself would have considered this brand old, but here we are, smoking it up as we have been since the mid 1800s. As ridiculous as that sounds, it certainly provides plenty of time for a company to learn how to make fine cigars. Of course, while we can’t imagine how much of the old way survives to today, we can report that a collaboration with Cuban-born A.J. Fernandez (Man O’ War, Diesel, Enclave) has breathed plenty of new life into this blend.

First off, it’s a beautiful 7x50 Churchill cigar with a gorgeous golden band reminiscent of H. Upmann’s history of high finance. Second, it smokes up fantastically, earning a 93-point rating from Cigar Aficionado. The tasty chocolate, cherry, and salty leather smoke carries a medium full strength, and the intriguing flavor is largely due to the wrapper. This is one of the best Churchill cigars to try thanks to a medio tiempo, high priming wrapper. They don’t always sprout out of a tobacco stalk, but when these leaves did, AJ knew what to do with them. Three years of careful fermentation later, here we are enjoying a fine cigar that adds another page to one of the longest stories in the cigar world.

E.P. Carrillo Core Plus Maduro Churchill Especial No. 7 Cigar – Irresistible Broadleaf Flavors

Ernesto Perez-Carillo has worked for quite some time in cigars, and like anyone who spends many years in the industry as a blender, there will eventually come a time when a man has to do his own thing. In this case, it’s E.P.’s factory La Alianza in the Dominican Republic. There, he has total control and can showcase a fine Connecticut broadleaf wrapper as in the 7x49 Core Plus Maduro Churchill. The Nicaraguan binder and filler, supply a nice woody, nutty core, but the broadleaf adds that chocolatey taste that brought the smoke into a more special category. With 92 points, this was Cigar Aficionado’s #23 cigar of 2019. With medium full strength, we’re getting the “plus” part of this smoke, and enjoying every draw. It’s a great Churchill to add to your humidor if you like a blend of woody and earthy flavor.

Espinosa Crema No.1 Churchill Cigar – A Gentle Goodbye

We’ve seen Churchills of various types on this list. The Espinosa Crema No. 1 Churchill is a nod to those who like to keep some gentler blends in their collection, without losing too much of the richness that makes cigars so damn nice. This one scored 91 points with the judges at Cigar Aficionado, and measures 7x48. It’s mild to medium, with a classic blend of Nicaraguan filler tobacco and an Ecuadorian Connecticut wrapper. Super smooth and buttery, it’s a Churchill from the “right side of the tracks.” We’re really enjoying the silkiness here, and hope you will too.

Please browse our selection of the best Churchill cigars at your leisure.

And here’s to Sir Winston. Rest in power, king.