Introduction: A Box of Legends
There’s something deeply satisfying about opening a beautifully crafted cigar box, especially when it contains not just one exceptional smoke, but three legendary cigars that have each earned their place in the pantheon of premium tobacco. The E.P. Carrillo Trilogy box set represents exactly this kind of rare treasure – a collection that brings together three of the most celebrated cigars from master blender Ernesto Perez-Carrillo Jr., two of which have earned the coveted Cigar of the Year title from Cigar Aficionado.
As someone who remembers their first tentative puffs on a premium cigar, I understand the overwhelming nature of choosing where to begin in the vast world of fine tobacco. This is precisely why I wanted to explore whether this prestigious trilogy box set might actually be an ideal starting point for beginners in 2025, despite its award-winning pedigree. After all, wouldn’t it be wonderful to begin your cigar journey with the best, rather than working your way up to them?
The E.P. Carrillo Trilogy contains the Pledge Prequel (No. 1 Cigar of 2020), the Encore Majestic (No. 1 Cigar of 2018), and the La Historia E-III (No. 2 Cigar of 2014) – a trifecta of excellence that showcases the breadth of Perez-Carrillo’s blending mastery. But beyond the accolades and reputation, what makes this collection special is how it offers three distinct smoking experiences that can educate and delight both novices and veterans alike.
Let’s embark on a journey through each of these remarkable cigars, exploring their construction, tobacco origins, flavor profiles, and ultimately, their suitability for those just beginning their love affair with premium cigars in 2025.
The Pledge Prequel: A Bold Introduction
The newest member of this illustrious trio, the Pledge Prequel, earned Cigar of the Year honors in 2020, and after spending time with this remarkable 5 x 50 robusto, it’s easy to understand why. The cigar features a Connecticut Habano wrapper – a leaf grown in the Connecticut River Valley but from Cuban seed – creating a beautiful marriage of American terroir and Cuban heritage.
Visually, the Pledge Prequel makes an immediate impression with its soft box-press, dark espresso brown wrapper, and noticeable veins that run along its length. There’s a substantial amount of oil present, giving it a luxurious sheen that hints at the richness within. When I first held it, I was struck by its solid construction – just short of rock-hard when gently squeezed, suggesting a well-packed, expertly rolled cigar.
The pre-light aroma offers a complex bouquet of cocoa nibs, milk chocolate sweetness, leather, creamy cedar, hay, and subtle almond notes. This complexity carries through to the cold draw, which adds hints of bitter espresso beans, earth, and vanilla bean sweetness.
Upon lighting, the Pledge Prequel announces itself with authority – a burst of spice on the tongue and black pepper on the retrohale that might initially seem overwhelming to a beginner. However, this intensity quickly settles, revealing the cigar’s true character: a dominant combination of creamy cedar and cocoa nibs, followed by notes of leather, earth, bread, peanut shells, espresso beans, and hay. There’s also a noticeable caramel sweetness on the retrohale that balances the experience beautifully.
For beginners, this initial intensity might be surprising, but I find it educational – it teaches patience and shows how a cigar can evolve dramatically from first light. The construction proves impeccable throughout the smoke, with a razor-sharp burn line and ideal draw resistance after a straight cut. The smoke production is generous, creating thick, aromatic clouds that enhance the sensory experience.
As the cigar progresses into its second third, the flavor profile shifts subtly. The caramel sweetness begins to recede while a distinct vegetal note reminiscent of asparagus emerges on the finish. The dominant flavors remain consistent – creamy cedar and cocoa nibs – but additional notes of leather, bitter espresso, toast, hay, cinnamon, peanut shells, and floral hints weave in and out, creating a complex tapestry of flavor.
The final third brings renewed vigor to both the spice and black pepper elements, while maintaining the core identity of creamy oak and cocoa nibs. The strength builds gradually throughout the smoke, starting relatively mild and finishing at a solid medium-plus intensity – a journey that I find perfect for beginners who want to experience how a cigar can build in character over time.
What makes the Pledge Prequel particularly suitable for beginners in 2025 is its remarkable balance between complexity and accessibility. While offering a sophisticated flavor profile that will satisfy experienced palates, it remains approachable enough for newcomers who are ready to experience a premium cigar that doesn’t overwhelm.
The Encore Majestic: A Nicaraguan Symphony
The Encore Majestic, crowned as Cigar of the Year in 2018, represents a different approach in the trilogy. This 5⅜ x 52 robusto is a Nicaraguan puro, meaning all of its tobacco – wrapper, binder, and filler – comes from Nicaragua. This single-country focus creates a harmonious expression of Nicaraguan terroir that showcases why these tobaccos have become so prized in the cigar world.
The Encore’s wrapper has a slightly lighter shade than the Pledge, with a reddish-brown hue that’s equally attractive but distinct. The box-press is elegant, and the construction feels solid and well-executed. What’s particularly impressive about the Encore is how it demonstrates the diversity possible within Nicaraguan tobacco – utilizing leaves from Condega, Jalapa, and other growing regions to create a complex blend.
Upon lighting, the Encore Majestic presents a different character than its trilogy sibling. The initial profile offers earth, pepper, and sweet notes in perfect balance. What surprised me most was the richness of the smoke – it’s full-flavored without being overwhelming, a difficult balance to achieve. As the cigar progresses, the earth notes gradually give way to more sweetness and floral characteristics, creating a dynamic evolution that keeps the palate engaged.
The construction proves excellent, with only minor waviness in the burn that quickly self-corrects. The draw has a slight resistance – just enough to produce optimal smoke without requiring effort. This kind of construction excellence is particularly important for beginners, who might be discouraged by cigars that require constant attention or relighting.
What makes the Encore Majestic particularly special is its perfect balance. As one reviewer aptly noted, “There is such a great balance between flavors that you can honestly tell this smoke was blended perfectly.” The pepper provides just enough kick without dominating, allowing the sweeter and more nuanced flavors to shine through.
For beginners in 2025, the Encore Majestic offers an ideal introduction to what a perfectly balanced cigar should taste like. It’s complex enough to be interesting but harmonious enough to be approachable. The medium-full strength builds gradually, making it accessible to those still developing their palate and tolerance.
The La Historia E-III: A Cross-Border Masterpiece
The elder statesman of the trilogy, La Historia E-III, earned the No. 2 spot in Cigar Aficionado’s 2014 rankings. This 6⅞ x 54 cigar is the largest of the three, offering a longer smoking experience and a different blend profile that showcases Perez-Carrillo’s range as a blender.
La Historia features a Mexican San Andrés Maduro wrapper, an Ecuadorian Sumatra binder, and a filler blend of Nicaraguan and Dominican tobaccos. This international combination creates a distinct character that stands apart from its siblings in the trilogy.
Visually, La Historia makes a statement with its dark, toothy wrapper and traditional round parejo shape (unlike the box-pressed formats of the other two cigars). The band is particularly ornate, featuring a vintage photograph that pays homage to the Perez-Carrillo family history – a touching detail that connects the smoker to the legacy behind the cigar.
The smoking experience begins with pronounced chocolate notes – a characteristic often associated with Mexican San Andrés wrappers. This dominant chocolate is joined by floral and herbal elements that create a sophisticated profile from the first puff. The draw is excellent despite the larger ring gauge, and the burn line remains impressively even throughout the smoke.
As La Historia develops, it reveals additional layers of complexity. Pepper notes emerge to complement the chocolate, while wood and leather join the chorus without overwhelming the primary flavors. What’s notably absent are the hay, earth, and barnyard notes that sometimes dominate cigars – instead, La Historia maintains its refined chocolate-forward character throughout.
The final third introduces espresso, sweetness, nuttiness, and bread notes, creating a satisfying conclusion to a remarkable smoke. As one reviewer noted, “It is no ‘yard cigar,’ no ‘car cigar,’ it needs to be savoured with time and concentration. Then it shines.”
For beginners in 2025, La Historia offers perhaps the most accessible entry point in the trilogy. Its chocolate-forward profile is immediately recognizable and enjoyable, while its gradual introduction of complexity serves as an excellent education in how a premium cigar evolves throughout the smoking experience. The larger size also allows newcomers to experience how a cigar’s character can develop over a longer smoking session.
The Trilogy Experience: Greater Than the Sum of Its Parts
What makes the E.P. Carrillo Trilogy box set particularly valuable for beginners in 2025 is how the three cigars function together as a comprehensive introduction to premium tobacco. Each cigar showcases different wrapper types, countries of origin, and flavor profiles while maintaining the consistent excellence that has become synonymous with the Perez-Carrillo name.
The Pledge Prequel demonstrates the magic possible with Connecticut Habano wrapper, the Encore Majestic showcases the harmony of Nicaraguan puros, and La Historia E-III reveals the rich character of Mexican San Andrés leaf. Together, they provide a masterclass in how wrapper varieties and tobacco origins influence the smoking experience.
All three cigars share impeccable construction – a hallmark of cigars produced at Perez-Carrillo’s Tabacalera La Alianza factory in the Dominican Republic. This consistency in quality makes the trilogy particularly beginner-friendly, as newcomers can focus on appreciating the flavor differences without being distracted by construction issues.
Comparison to Other Beginner Sets in 2025
While the E.P. Carrillo Trilogy represents premium cigars at their finest, it’s worth comparing it to other options marketed specifically to beginners in 2025.
Many starter sets in today’s market focus on milder cigars with Connecticut Shade wrappers, operating under the assumption that beginners prefer milder experiences. Popular options include the Arturo Fuente Hemingway Sampler, the Ashton Classic Collection, and various mild sampler packs from major retailers.
These traditional beginner sets certainly have their place, and the milder profiles can be less intimidating for absolute newcomers. However, they often lack the complexity and character that make premium cigars truly special, potentially giving beginners a limited understanding of what fine cigars can offer.
The E.P. Carrillo Trilogy takes a different approach. Rather than assuming beginners need to start with the mildest options, it offers three medium to medium-full bodied cigars that showcase the depth and complexity possible in premium tobacco. This approach respects the intelligence and curiosity of newcomers, inviting them to dive into the deep end of cigar appreciation rather than wading in the shallows.
Another popular option for beginners in 2025 is the “World Tour” style sampler, which includes cigars from various countries to showcase different growing regions. While these can be educational, they often include cigars of varying quality levels. The E.P. Carrillo Trilogy, by contrast, maintains consistent excellence while still demonstrating regional differences through its varied wrapper selections.
Pricing and Availability in 2025
When the E.P. Carrillo Trilogy was first released in 2021, it carried a suggested retail price of $36 for the three-pack. In 2025, the set typically retails between $45-55, depending on local taxes and retailer markup. While this represents a premium price point compared to some beginner samplers, it offers exceptional value considering the pedigree of the cigars included.
Availability has improved significantly since the initial release. While the first shipment was limited to just 100 boxes, E.P. Carrillo has continued production due to high demand. The set can now be found at most premium cigar retailers, both brick-and-mortar and online. Specialty shops like Small Batch Cigar, Cigar Page, and Neptune Cigar consistently carry the trilogy, often with promotional pricing during special events.
For beginners concerned about the investment, it’s worth noting that purchasing these three cigars individually would typically cost $10-15 more than buying the trilogy set, making it an economical way to experience these exceptional smokes.
Is the E.P. Carrillo Trilogy Relevant for Beginners in 2025?
After thoroughly exploring the E.P. Carrillo Trilogy, the question remains: Is this premium set truly appropriate for beginners in 2025?
My answer is an enthusiastic yes – with one caveat. This set is ideal for the curious beginner who approaches cigars with genuine interest and openness to experience. If you’re someone who wants to understand what makes premium cigars special and is willing to invest time in developing your palate, the trilogy offers an unparalleled education.
However, if you’re looking for the mildest, simplest introduction to cigar smoking, there are certainly more accessible options available. The trilogy demands attention and appreciation – these are cigars to be savored mindfully, not smoked casually while multitasking.
What makes the trilogy particularly relevant in 2025 is how it aligns with broader consumer trends toward quality over quantity. Today’s beginners in many luxury categories – whether wine, whiskey, or cigars – often prefer to start with fewer, better experiences rather than working their way up from entry-level products. The trilogy caters perfectly to this mindset.
Additionally, the set offers excellent value in an era of rising cigar prices. While premium cigars have seen significant price increases in recent years due to supply chain challenges and increased regulation, the trilogy remains reasonably priced considering the quality and accolades of the cigars included.
Conclusion
The E.P. Carrillo Trilogy box set represents a remarkable opportunity for beginners to experience three of the finest cigars produced in recent years. Rather than starting your cigar journey with forgettable smokes, why not begin with cigars that demonstrate the heights this art form can achieve?
What I appreciate most about this collection is how it respects the intelligence and curiosity of newcomers. It doesn’t assume beginners need to be coddled with the mildest, simplest cigars – instead, it invites them to dive into the rich complexity that makes cigar smoking such a rewarding pursuit.
The trilogy also offers an efficient education in premium tobacco. By experiencing these three distinct blends, beginners can quickly develop their palate and preferences, gaining insights that might otherwise take months or years of exploration.
For those beginning their cigar journey in 2025, the E.P. Carrillo Trilogy represents not just three exceptional smokes, but a passport to the world of premium tobacco – a world where craftsmanship, heritage, and flavor create experiences worth savoring. Whether you’re just starting out or looking to experience some of the finest cigars of the past decade, this trilogy deserves a place in your humidor.
