There’s a factory vitola designation, probably stamped on a cedar box in Havana sometime in the mid-twentieth century, that simply reads: Julieta No. 2. Seven inches, 47-ring gauge. A size that had already been around for decades — Romeo y Julieta had even offered a version called the Clemenceau, named for the French Prime Minister who also had a taste for large Cuban cigars.
Then Winston Churchill visited Cuba in 1946, and the cigar world got its most durable brand name.
The Man Who Gave a Size His Name
Churchill’s relationship with cigars started in 1895, during a trip to Cuba as a young war correspondent. He was twenty years old. He would go on to smoke between eight and ten of them a day for the next sixty years.
That number requires some context. Churchill was not a careful, reverent smoker who honored each cigar with deliberate ceremony. He chewed on them. He let them go out and relit them. He frequently discarded a half-smoked cigar and started a fresh one. His home in Kent maintained a cellar holding three to four thousand at any given time. During World War II, he had a special oxygen mask designed that allowed him to smoke mid-flight — the man understood that pressurized cabins at altitude weren’t suitable for open flame, and he solved the problem accordingly.
His preferred brands ran toward Romeo y Julieta and La Aroma de Cuba, with a consistent preference for larger formats. When the Romeo y Julieta factory formalized the naming of the Julieta No. 2 after his 1946 visit — sometime between that year and the early 1950s, accounts vary slightly — they were recognizing what everyone who’d watched him work already knew: the man and the format were a natural fit. Both took up space. Both commanded patience from whoever was in the room. Both communicated something serious about the person holding them.
What a Churchill Actually Is
The standard: 7 inches long, 47 to 50-ring gauge. Some manufacturers shade toward 6¾; others push to 7⅜. The ring gauge has crept up modestly in recent decades, and you’ll find Churchill-labeled cigars running to 52 or 54 at some houses. But the classic expression — the one the format was built around — is the long, relatively lean version. Elegant rather than beefy.
What that dimension does to a smoke is specific and worth understanding if you’ve never committed ninety minutes to one.
The smoke channel is long. That matters because smoke cools as it travels, and a cooler smoke delivers flavor without the harshness that comes from heat. A robusto at five inches produces the same tobacco character faster and hotter; a Churchill gives those compounds time to settle before they reach your palate. The result is a progressively developing smoke rather than one that hits the same note for an hour.
The format also demands blending discipline. When a cigar runs ninety minutes, the thirds matter — they need to be distinct without being jarring, each building on what came before. A Churchill that smokes identically from light to nub is a wasted canvas. The best ones open with restraint, deepen through the middle, and reward patience in the final stretch. Designing that arc over seven inches is harder than building a great robusto. It’s the difference between writing a short story and writing a novel.
How the Great Houses Have Handled It
Romeo y Julieta still makes the Churchill. The Cuban original is among the most storied production cigars in the world — cedar, cream, subtle floral notes that age remarkably well, medium body that reveals more complexity over time than it initially suggests. It’s the reference point. Everything else is measured against it.
Montecristo has the Churchill in both its Cuban and Dominican expressions. The Cuban version earned a 91 from Cigar Aficionado. The Dominican Original Churchill, wrapped in Connecticut shade, is a softer, more approachable version — a good entry point for anyone who wants the format without the full complexity of the Cuban leaf.
Davidoff entered the conversation in 2007, when Winston Spencer-Churchill — the statesman’s grandson — collaborated with them on a line bearing the family name. That line was later reblended and relaunched in 2015 as the Davidoff Winston Churchill series, built in two expressions: the Original Series (Ecuadorian Habano Rojiza wrapper, medium body, cedar and toasted nuts) and the Late Hour Series, launched in 2017, which is the genuinely interesting one.
The Late Hour uses a Habano Oscuro wrapper and filler that includes Nicaraguan Condega leaf aged six months in Speyside single-malt Scotch whisky casks. It’s full-bodied, focused, and tastes like something you smoke after midnight when the conversation has gotten serious. Davidoff — whose house style tends toward the refined and restrained — releasing a full-bodied Scotch-aged cigar is the brand acknowledging something about Churchill’s actual life: the late-night cognac-and-cigar sessions that ran to 1 or 2 AM, the work that happened when the official day was done. The Late Hour isn’t a tribute to the statesman in the Cabinet room. It’s a tribute to the person he was at the end of the evening.
Their Limited Edition 2025, called The Artist, honors Churchill’s often-overlooked secondary career as a painter. He completed over five hundred paintings. The Churchill who lit up during wartime Cabinet meetings is the one history remembers — but there was another version of him, quieter and meditative, standing in front of a canvas. That one smoked too. The format suits both.
Why the Format Still Matters
The Toro won the size wars. Ring gauges ballooned through the 2000s and 2010s, and the default modern cigar sits around 6 x 52. The Churchill, with its more modest ring and longer body, fell slightly out of fashion as the industry chased density and boldness over elegance and duration.
But something persistent has happened. Blenders who want to make a statement — who have a tobacco combination they believe in and need room to let it develop — keep returning to the Churchill. The format is too specific to be casual. A manufacturer doesn’t put a blend in a Churchill because it’s convenient; they do it because they believe the tobacco earns that kind of canvas.
There’s also the time argument. A Churchill demands ninety minutes. That’s not a smoke you light between meetings. Lighting one is a declaration: you’re done rushing for a while. Whatever felt urgent an hour ago will still be there when you’re finished, and you’re going to let it wait.
Churchill himself — who ran a world war on cigars, champagne, cognac, and almost no sleep — understood something the modern world tends to undervalue: that the act of pausing, deliberately and without apology, is not an indulgence. It’s infrastructure.
The cigar that carries his name remains the best argument for that idea.
Ready to start? The Romeo y Julieta Churchill (Dominican) is the accessible entry point. The Davidoff Winston Churchill Late Hour is where you go when the evening has earned it.