The 5 Years of #1 Cigar of the Year V2 Sampler is a celebration of modern cigar greatness — five blends that each rose above the rest to earn the highest honor in the industry. These aren’t just highly rated cigars; they are the cigars that defined their respective years, recognized for exceptional construction, balance, and unforgettable flavor.

First in the lineup is the Casa Magna Colorado Robusto, which stunned the cigar world with a towering 97 rating when it captured the #1 spot. This Nicaraguan puro delivers bold, earthy richness layered with dark cocoa, espresso, and a peppery finish that showcases depth without overpowering the palate.

Next is the My Father Flor de Las Antillas Toro, a Cuban-inspired masterpiece that earned a 96 rating on its way to the top. Silky, box-pressed, and beautifully balanced, it offers notes of toasted cedar, sweet cream, nutmeg, and a gentle spice that builds steadily from foot to nub.

The E.P. Carrillo Encore Majestic Robusto, rated 96 in its winning year, brings lush Nicaraguan character to the forefront. Expect creamy smoke layered with coffee, earth, and subtle sweetness, all delivered with the refined balance that defines Ernesto Perez-Carrillo’s blending style.

Following it is the E.P. Carrillo Pledge Prequel Robusto, which claimed cigar immortality with an incredible 98 rating. Rich yet polished, this cigar delivers waves of cocoa, dark fruit, espresso, and oak, with a velvety texture that makes every draw feel luxurious.

Rounding out the sampler is the My Father The Judge 560 Box Pressed, a bold Nicaraguan powerhouse that earned a 97 rating when it took top honors. Deep notes of leather, spice, roasted nuts, and dark chocolate create a full-bodied experience that remains remarkably smooth and controlled.

Together, these cigars tell the story of evolving excellence — from the trailblazing Casa Magna to the modern sophistication of Pledge. Each represents a moment when craftsmanship, tobacco selection, and blending artistry aligned perfectly.

Vintage Vinny says: “This sampler is like opening a time capsule of greatness — every cigar changed the conversation when it won.”
Nicaraguan Nick adds: “You can taste the progression of Nicaraguan blending across these five legends.”
Toro Tommy notes: “Different factories, different styles — but everyone delivers championship-level balance.”

For collectors, enthusiasts, or anyone wanting to experience what true top-tier cigars taste like, this sampler offers a rare chance to enjoy five defining blends side by side.

All tasting notes and quotes from our “Cigar Sommeliers” are voiced by fictional AI personas created for educational and storytelling purposes. Flavor descriptions reflect general impressions; individual experiences may vary.

A sweet and affordable assortment of 5 Years of #1 Cigar of The Year includes 1 of each of the following cigars....

1 - 2008 Casa Magna Colorado Robusto

1 - 2012 My Father Flor de Las Antillas Toro

1 - 2018 E.P. Carrillo Encore Majestic Robusto

1 - 2020 E.P. Carrillo Pledge Prequel Robusto

1 - 2024 My Father The Judge 560 Box Pressed