Honoring Winston Churchill: A Tribute Through the Lens of Cigar History

As we commemorate the birthday of Sir Winston Churchill on this 30th of November, it is only fitting to reflect on one of his most enduring legacies in the world of cigars: the iconic Churchill size. Churchill’s name has become synonymous with this timeless vitola, yet the story behind its origins is steeped in mystery, myths, and fascinating anecdotes.

To mark this occasion, we revisit an insightful article by Simon Chase, one of the most respected figures in the cigar world, whose expertise sheds light on Churchill’s enduring connection with Havana cigars. Chase’s exploration of Churchill’s smoking habits, the legends surrounding his favorite brands, and the historical moments that intertwined cigars with Churchill’s remarkable life serves as a perfect tribute to the man himself.

In this detailed narrative, we uncover the role cigars played in shaping not only Churchill’s personal image but also their surprising influence during pivotal moments in history. From wartime generosity to post-war diplomacy, the relationship between Churchill and his cigars remains a source of intrigue and inspiration.

Let us dive into this journey and celebrate the legacy of a leader whose presence, like a fine cigar, lingers far beyond his time.

You would imagine that the day when the word Churchill entered the language of cigars to describe the size we all know is well documented.

It is not.

Instead there are countless legends, rumors and hypotheses not only about the origins of the size name but also about what cigars Winston Churchill actually smoked particularly during and after the Second World War.

In 2007 a young Scottish journalist and author named Stephen McGinty published a book entitled “Churchill’s Cigar” (Macmillan £12.99). Early on in his research into the great man’s passion Stephen contacted me confident that I would be able to provide a few basic facts.

I furnished him with the conventional wisdom that Romeo y Julieta was the great man’s preferred brand, that the date the size was introduced followed closely on the heels of Churchill’s only 20th century visit to Havana in February 1946 and that the first Churchill cigar was the Romeo. However I had no supporting evidence, so I asked Stephen to seek out the truth in which I would be extremely interested.

His extensive research into the Churchill archive and to a lesser extent amongst the records in Havana revealed a plethora of previously unknown information, at least to me.

For example, although some seemingly reputable sources claim that the Romeo y Julieta factory sent regular shipments to Churchill throughout the war, Stephen could find no evidence of it. Instead he unearthed an intriguing story about a New York businessman named Samuel Kaplan, who was so impressed by Churchill’s single-handed stand against the Nazis that he resolved at his own expense to keep the British Prime Minister supplied with first class Habanos.

Kaplan’s gifts were large La Corona, 5,000 of which he had secured from Havana in the middle of 1940. The first batch was sent to the British Embassy in Washington towards the end of the year to coincide with one of Churchill’s frequent visits to the USA.

Further deliveries were sent directly to London causing Churchill to refer to them in a letter to Kaplan as “Those wonderful cigars that have cheered my long path through the war.”

In another letter thanking Kaplan for his generosity Churchill reported: “You will be interested to know that the bands on which you have had my name printed are regarded as souvenirs and gladly accepted wherever I go.”

This is the first record of the name Churchill appearing on a cigar.

However their exact size remains a mystery despite that fact that a part smoked example can be found behind glass in the Churchill Museum section of Cabinet War Rooms in London. As you can see one end is chewed and the other has been cut off in its prime. Although I was not permitted on a recent visit to handle the relic, I would estimate that it is fatter than the 47 ring gauge found on a Churchill and was probably a Double Corona in size.

Kaplan’s were not the only cigars Churchill received as gifts during the war. Literally tens of thousands flooded in from well-wishers most of which were sent to the incinerator either because their quality did not meet his exacting standards, or because their source worried the security services.

On two occasions the Cuban government sent cigars to London. The most notable arrived at 10 Downing Street on 19th September 1941 during a meeting of the Chiefs of Staff held to decide how much military aid Britain could afford to send to the Soviet Union. After many hours of bitter dispute the meeting was in deadlock. Then Churchill decided to hand a cigar to each member of the group. They lit up and within thirty minutes the matter was resolved; a perfect example of how Havana cigars have influenced the course of world history.

Several people claim that, during his February 1946 visit to Havana, Churchill had gone to see the Romeo factory and that this sparked the birth of the cigar. Again Stephen could find no record or photograph of such a visit.

What he did find out was that Churchill had met a new cigar patron, another businessman, this time a Cuban named Antonio Giraudier. Giraudier shared Kaplan’s admiration for the great man and supplied cigars to Churchill free of charge up until the Cuban revolution.

At Churchill’s request, Giraudier’s first gift was 500 Por Larrañagas, probably the Magnum size (6.625 inches by 50 ring gauge), but by 1950 he was sending a brand called Don Joaquin made by a small manufacturer named Joaquin Cuesta. Churchill liked these cigars, but he was less enthusiastic about the band, which carried a picture of Señor Cuesta resembling a mafia boss. The request came from London to remove his image, which was duly done.

A box of these cigars with the amended bands can be seen today in the museum of J. J. Fox of St. James’s, the shop where, when it was known as Robert Lewis, Churchill was a regular customer. They measure 6.5 inches by 48 ring gauge, shorter and a little fatter than a true Churchill.

So where does this leave us on the origin of the Churchill size? I must admit that my research was floundering until I managed to contact a man called Peter Knight, whose family company Knight Brothers had been the UK importers of Romeo y Julieta up until 1990.

Peter recalled that his father’s cousin David Knight together with John Croley of Robert Lewis had approached the Churchill family to ask if they could use his name on a Romeo y Julieta cigar. Precisely when this took place he was not sure. Anyway the Churchills had agreed.

The size chosen by Knight and Croley was 7 inches by 47 ring gauge, which is known in the Cuban factories as the Julieta No. 2. It had been sold by Romeo y Julieta since the 1920s or’30s under two names: the Prince of Wales and the Clemenceau. The Prince of Wales was not, of course, the current incumbent, Charles, but his great uncle (later the Duke of Windsor) with whom Churchill had sided during the 1936 abdication crisis.  And Clemenceau was France’s cigar-loving First World War Premier, who coincidentally had toured the trenches in 1918 with Churchill, then Britain’s Minister for Munitions.

For a time I assumed that this had happened after Churchill’s death in January 1965, therefore after the Cuban revolution, because Peter Knight had told me how touchy Churchill was about his name being exploited for commercial reasons. Then, on a Saturday morning visit to my local cigar shop, Cigars Unlimited in Fulham, I was shown no less than three remarkable full boxes of Romeo y Julieta Churchills in aluminum tubes that had been sold by Dunhills in 1956.

Not only did they have all the correct marks for the period, but Peter had also explained to me that the original idea agreed with the factory in Cuba was to introduce the Churchill only in aluminium tubes, leaving the untubed version of the same size as either Prince of Wales or Clemenceau.

By the time you read this article, these original Romeo Churchills, probably amongst the first ever made, along with an outstanding collection of other Cuban cigars from the 1950s, 60s and 70s will have been sold at auction by Cigars Unlimited. If you want to know how much they made; visit www.cigarsunlimited.co.uk

Faced with this evidence, the date can be narrowed down to between 1956 and 1952, which was the year when dollar controls were first lifted by the British Government and Havanas could be imported to the UK for the first time since 1939.

The spread of the Churchill name to other brands like Punch and Bolivar did not take place until the early 1980s, by which time the name Churchill was firmly established in our lingo for a 7 inch, 47 ring gauge cigar.

Did Churchill ever smoke the cigar that bears his name? Possibly not; Peter Knight is adamant that the cigar Churchill chose to buy, as opposed to receive as gifts, was called the Romeo y Julieta Piramide No. 1, no doubt a torpedo measuring 6.125 by 52.

If the history that lies behind the cigars you smoke appeals to you a visit to London could prove rewarding.

Smoking restrictions apart, there has never been a better time for a cigar enthusiast to cross the pond mainly due to a new toy that has just been produced by a company called Cities in Sound. Cities in Sound makes award winning audio walking tours of great European cities that you download for a modest fee from its website onto your iPod or MP3 player. Then, when you get to your destination, you simply turn it on, follow the instructions and enjoy an audio tour conducted by experts which will reveal not only the well known landmarks but also many hidden secrets as well.

Its proprietor, Nic Wing is a cigar smoker and he has just added a new title to his portfolio: The Cuban Cigar Walk: London.

It starts at the famous statue in Bond Street where Franklin D. Roosevelt and Winston Churchill are seated together on a bench. It then leads you on a walk thru many of London’s most famous and lesser known streets and squares ending at the Cabinet War Rooms and Churchill Museum. Along the way you are introduced to four of the city’s most renowned cigar merchants: Alfred Dunhill, now in its newly refurbished 18th century splendor at Bourdon House, Desmond Sautter’s Mayfair store, Edward Sahakian’s Davidoff Shop and J. J Fox & Robert Lewis where the Churchill cigar was conceived.

The proprietors or managers of each shop have contributed their wisdom to the soundtrack and you will receive a memento of your pilgrimage at the last shop you visit.

But perhaps most useful of all, you will learn of all the places where you are welcome to sit down, light up and enjoy a good cigar. To find out more visit www.citiesinsound.com