ReviewsDominican

E.P. Carrillo Pledge Prequel: The 2020 Champion, Earned

Name: E.P. Carrillo Pledge Prequel: The 2020 Champion, Earned
Item: Prequel
Rating: 93
Author: Theo Bennett

Reviewed cigar

E.P. Carrillo Pledge Prequel

Brand: E.P. Carrillo
Line: Pledge
Vitola: Prequel
Wrapper: Connecticut Habano (USA)
Binder: Ecuador
Filler: Nicaragua
Size: 5 inches × 50 ring
Strength: Full
Origin: Dominican Republic
Price: $11–15
Smoking Time: 75 min

July 29, 2026

By Theo Bennett

Last updated: July 29, 2026

Construction

Draw

Flavor

Burn

Value

Overall / 100

Who should buy

Smokers who want a bold, evolving full-bodied cigar
Anyone curious to taste a genuine Cigar of the Year
Collectors drawn to a distinctive Connecticut Habano wrapper

Who should skip

Milder palates put off by a spicy, peppery opening
Smokers wanting a light, easygoing everyday cigar
Beginners not yet used to full strength

The 2020 champion, and it earned it

The E.P. Carrillo Pledge Prequel was Cigar Aficionado's number one Cigar of the Year for 2020, rated 98 - a landmark for Ernesto Perez-Carrillo Jr. and his Tabacalera La Alianza factory in the Dominican Republic. Its signature is the wrapper: a Cuban-seed Habano varietal grown in Connecticut, distinct from the mild shade leaf the state is famous for. I judge a cigar on whether it has genuine character or is merely competent, and awards make me more skeptical, not less. This one holds up to the scrutiny.

The flavor arc is the whole argument. It opens bold and zesty - black pepper and spicy oak with licorice underneath - then transitions into a rich core of black cherry, dark cocoa and espresso, finishing on toasted almond. That is a real evolution, bold to rich to polished, backed by flawless construction: straight burn, firm ash, effortless draw. Cigars that win these titles are sometimes safe crowd-pleasers. This is not that; it has genuine intensity and complexity.

On value, it is that rare top-rated cigar that is actually attainable, running roughly eleven to fifteen dollars - a fair ask for this quality, even if prices crept up after the win. If you want the same maker with a darker, sweeter San Andres profile, the E.P. Carrillo La Historia E-III sits near eleven dollars and is superb. If you want comparable full Ecuadorian-Habano-style power for a little less, the Oliva Serie V Robusto delivers around ten. But the Prequel offers something specific - that bold-to-refined evolution and a genuinely distinctive Connecticut Habano wrapper - and it is one of the few Cigar of the Year winners I would tell someone to buy without a second thought.

Where it fits is broad for a cigar this good: it works as a special-occasion smoke that lives up to the hype, and as a periodic treat for anyone who likes bold, evolving tobacco. It is not a mild everyday cigar, and a beginner might find the opening intense. But for a smoker who wants to taste why this won its title, the Prequel is a rare recommendation with no asterisk - buy one, give it an hour, and let the arc from pepper to cocoa make the case itself.

Pre-light & Cold Draw

A Connecticut Habano wrapper - Cuban-seed leaf grown up in Connecticut, not the pale shade most people picture - so it reads a rich, oily medium-brown. The robusto is firm and evenly filled, a hint of a press to it. The cold draw came sweet with cedar and a dry spice on the lips. This is the cigar Cigar Aficionado crowned number one in 2020, and there is a certain pressure smoking one of those: it either earns the title or it doesn't. I cut it curious.

First Third

It comes out swinging. Black pepper and a zesty, spicy oak lead the first inch, bright and lively, with a licorice note threading underneath. This is a bold opening - not harsh, but assertive, the kind that wakes up the palate. The draw was excellent and the burn set off razor-straight, laying a firm ash. What impresses early is that the intensity has shape to it; there is licorice and a dark-fruit sweetness organizing the spice rather than just heat for its own sake.

Second Third

The middle is where it justifies the trophy. The pepper mellows and a black-cherry sweetness rises, dark cocoa building underneath, espresso arriving behind that. It goes from bold to rich, layering flavor without losing its backbone. This is genuinely complex smoking - the sort of second third you slow down for. The construction stayed flawless: an even burn I never touched, a firm grey ash holding well past an inch. Everything is working at once here.

Final Third

The close brings a toasted almond note in behind the cocoa and espresso, the pepper settling to a warm hum, the body sitting at a comfortable full through roughly seventy-five minutes. Some smokers find it mellows to medium-full by the end; on my palate it stayed rich and substantial to the nub. It never turned hot or bitter. This is a cigar that opens loud, deepens, and finishes with real polish - the arc a champion should have.

Pros

Genuine evolution: bold pepper and oak into black cherry, cocoa and espresso
Flawless construction - straight burn, firm ash, effortless draw
A top-rated Cigar of the Year that stays attainable at $11-15

Cons

Bold, spicy opening may be much for milder palates
Prices crept up after the 2020 award
Full strength throughout - not a light, easygoing smoke

Frequently asked questions

Does the Pledge Prequel really earn its 2020 title?

I came in skeptical, because awards make me more critical, not less. It holds up: the arc from bold pepper and oak into black cherry, cocoa and espresso is genuine, backed by flawless construction. This is not a safe crowd-pleaser - it has real intensity and complexity.

What is unusual about the wrapper?

It is a Cuban-seed Habano varietal grown up in Connecticut, not the pale shade leaf the state is famous for. That gives it a rich, oily medium-brown look and a lot of its character. It is one of the more distinctive wrappers in this price bracket.

Is it too strong for a beginner?

The opening is bold and spicy, so a new smoker might find it intense. It stays full through most of the smoke. I would steer a beginner to something gentler first and save this for when full strength is welcome.

Is it worth the price?

Yes, and that is rare for a top-rated cigar. At roughly eleven to fifteen dollars it is genuinely attainable for this quality, even if prices crept up after the win. I would buy one without a second thought.

What if I want the same maker but sweeter or cheaper?

The E.P. Carrillo La Historia E-III near eleven dollars gives you a darker, sweeter San Andres profile and is superb. For comparable full power for a little less, the Oliva Serie V Robusto delivers around ten. But the Prequel's bold-to-refined evolution is its own thing.

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