H. Upmann Sir Winston

Description

Winston Churchill consumed so many of these cigars that Habanos S.A. eventually named the entire vitola after him. Seven inches of hand-rolled Cuban tobacco, crafted in the same format the British Prime Minister reached for during the darkest hours of World War II. This isn’t just a cigar—it’s a ritual, a commitment, and one of the last true Churchills remaining in the Cuban portfolio.

The Smoking Experience

First Third: The Sir Winston opens with remarkable grace. Cedar greets you immediately—not the sharp pencil-shaving kind, but warm, aged wood like opening an antique humidor. Floral notes dance at the edges, delicate and unexpected. A whisper of graham cracker sweetness develops on the retrohale. The draw is perfect, offering just enough resistance to slow you down and make you pay attention. This is a conversation starter, not a sprint.

Mid-Section: Here’s where the magic happens. The cedar mellows into cream, and suddenly you’re tasting marzipan—those almond paste confections your grandmother kept in a tin. Dark chocolate emerges, rich and bittersweet, intertwined with roasted coffee notes. The smoke is clean, pale grey, voluminous without being aggressive. This transition from early florals to nutty sweetness is one of the most rewarding evolutions in the Cuban catalog.

Final Third: The sun sets on this smoke with dignified intensity. Not stronger in nicotine—the Sir Winston never punches—but deeper, more contemplative. Burnt almonds join the chocolate. A damp earthiness enters, that unmistakable “Upmann funk” that tells you this tobacco has been aged properly. Leather notes take center stage while maintaining that creamy backbone. The finish lingers for an hour after you’ve set down the nub.

Flavor Profile

The Legacy of H. Upmann

Founded in 1844 by German banker Herman Upmann, this marca began as a way to send cigars back to Europe. The bank eventually failed, but the cigars endured—a testament to where true value lies. The H. Upmann factory, known as José Martí, sits in the heart of Havana and has produced some of Cuba’s most celebrated smokes for nearly two centuries. The Sir Winston represents the pinnacle of their craft: unhurried, sophisticated, built for those who understand that great things require time.

Perfect Pairings

• Whisky: Highland single malt—Glenfiddich 18 or Macallan 12. Honey and heather notes complement without competing. Avoid peaty Islay malts that would drown the cigar’s subtlety.
• Rum: Diplomático Reserva Exclusiva or Ron Zacapa 23. The vanilla and caramel notes mirror the cigar’s marzipan sweetness.
• Coffee: Medium roast Ethiopian Yirgacheffe. Its bright, fruity acidity cuts through the smoke’s richness while echoing the chocolate notes.
• Non-Alcoholic: Rich dark hot chocolate. The bitterness creates harmony with the cigar’s cocoa undertones.

Ideal For

The H. Upmann Sir Winston demands two hours of uninterrupted peace. This is not your Tuesday lunch break cigar. Save it for milestone moments: a promotion, a reunion, a clear evening with nowhere to be. Experience level matters less than patience—beginners who can commit the time will find an approachable medium body, while veterans will appreciate the layered complexity that reveals itself slowly. If you chase Nicaraguan ligero bombs for their nicotine hit, look elsewhere. But if you want a cigar that tells a story, that rewards attention with nuance, that leaves you thinking about it days later—this is the one Churchill chose for a reason.

Collector’s Note: The Sir Winston improves dramatically with age. A few years in your humidor transforms it from good to transcendent. If you find a box, smoke one now to understand the baseline, then forget the rest exists for three years. Your future self will thank you.