What Cigars Did Winston Churchill Smoke? The Man Behind the Churchill Size

Ray, a retired Marine who sits at our Thursday table, only smokes Churchills. Long, elegant, seven inches or so. When Theo asked him why, Ray said, "Because it was good enough for Churchill." Which raised a better question: what did Churchill actually smoke? The answer surprised all of us, Ray included.

It started in Cuba, in 1895

In late 1895, a young British officer named Winston Churchill traveled to Cuba with a fellow officer to observe the Spanish army's campaign against Cuban rebels. He was there partly as a soldier and partly as a war correspondent. He turned 21 on the island.

According to Cigar Aficionado's profile of him, Churchill and his companion arrived in Havana and spent their first days living on little more than two local specialties: oranges and cigars. He'd been introduced to cigars before the trip, but Cuba is where the habit took hold. From then on, for Churchill, a cigar meant a Cuban cigar.

The brands he favored

Two names come up again and again: Romeo y Julieta and La Aroma de Cuba.

Romeo y Julieta is the best documented. The records of J.J. Fox, the London tobacconist that supplied him, show repeated purchases of Romeo y Julieta cigars, including sizes that are no longer part of the main Cuban Romeo line. La Aroma de Cuba, the Cuban brand he enjoyed, no longer exists in its original form. (There is a modern, non-Cuban brand that carries the name today.)

Here's what surprised Ray. Churchill didn't stick to one size or one brand. According to reporting based on those J.J. Fox records, he bought many different brands and sizes, often several at once. He was, in that sense, much like a modern cigar smoker: curious, exploring, not locked into a single vitola. Cigar Aficionado also recounts a 1963 telegram in which he ordered a gift box for his grandson, asking for cigars "of good quality, but not quite as good as the Romeo & Juliet." Even late in life, he knew exactly where his favorite sat.

How the Churchill size got its name

The Churchill is one of the classic cigar sizes. In Cuba it's traditionally about 7 inches long with a 47 ring gauge, named in his honor. Outside Cuba, you'll see "Churchill" used a little more loosely, typically around 7 inches with a ring gauge somewhere in the high 40s to around 50.

The irony is that the size that carries his name wasn't the only thing he smoked, and the name came from his fame rather than from a single cigar he was loyal to. He became the face of the long cigar because he was almost never photographed without one.

How he kept them

Churchill took storage seriously. At Chartwell, his country home in Kent, England, he kept thousands of cigars, mostly Cuban, in a room next to his study. Accounts describe boxes on shelves labeled by size and by whether the cigars were wrapped in cellophane or not.

I build cabinets for a living, and I love that detail. It's a system. A man running a country during a world war still had his humidor organized by size and wrapper. That's not excess. That's someone who cared about getting the details right.

What his habits can teach a modern smoker

I'm not here to tell you to smoke like Churchill. The stories about how much he smoked are part of the legend, and quantity is the least interesting thing about it. What's worth borrowing is his approach.

He explored. He didn't let one brand or one size define him. If you've been smoking the same cigar for a year, try a different size of it. You'll be surprised how much a change in length and ring gauge changes the smoke.

He knew his favorite. Exploring doesn't mean having no opinion. After all that variety, he still knew Romeo y Julieta was his benchmark. Build your own benchmark cigar, the one you measure everything else against.

He kept things organized. Labeled shelves at Chartwell. A tobacconist with a record of every order. You don't need a room, but you do need to know what you have and what you thought of it. (A sealed container works fine; here's how to store cigars without a humidor.)

He took his cigars seriously and himself less so. The Churchill cigar is part of his public image because it was simply part of him, present through the hardest years of his life, not a prop.

Smoking a Churchill today

If you want to try the size, give it the time it asks for. A Churchill can easily run an hour and a half or more. That's a whole ballgame, or a long dinner conversation, or a few sides of a good record. Don't start one if you have somewhere to be.

A few ways in, all in the LongestAsh Library:

• A classic Cuban-heritage brand in the Churchill size, like the Montecristo Churchill.
• The modern La Aroma de Cuba Churchill, a nod to one of his old favorites by name.
• Davidoff's Winston Churchill line, made in tribute to him.
• Or pick a cigar you already love and try it in its Churchill size, and notice what changes.

The last word goes to Ray

After all this, Theo asked Ray if he was going to start smoking other sizes. Ray thought about it for a long draw and said, "Maybe a robusto. On a weeknight." From Ray, that's a revolution.

When you're ready, log your Churchill in LongestAsh. Note the length, the pairing, and how long you sat with it. Churchill would have appreciated the record keeping.