Cuban cigars can be frustratingly inconsistent. Cigars from the same box can vary wildly. Not always, but it does happen. Consistent inconsistency, if you like.

That said, in general, they hold their “DNA,” their flavors, their style. Quality may exceed expectations or occasionally fall short, but this has become part of the fun – although, to be honest, I think I would rather have a box of superb smokes every time than a lottery. Still, it is what it is.

We need to remember that this is a handmade product from start to finish. Some rollers are able to perform magic, others not so much.

If you purchase a box of Cubans, there is very little chance that the same roller is responsible for all the cigars in that box. Cigars tend to be grouped so that a box has a consistent appearance throughout. Leaves can vary in color, so you might have cigars from quite a few rollers. This is one of the reasons quality can vary. And never was this more evident than from some recent tastings.

One of the things I do is cigar videos with an industry friend – usually on my balcony with me providing a range of drinks to try with the cigar (see www.friendsofhabanos.com). These days, thanks to isolation, we are doing it by Zoom, so I am still fine for drinks, but my friend is getting grumpier and grumpier about missing my half of the contribution. This falls very much into the category of “first-world problems.”

Box of H. Upmann Sir Winston Cuban cigars

Recently, we looked at an absolutely classic cigar, the H. Upmann Sir Winston (AUD$1,750/USD$600), a famous cigar. Unfortunately, chunks of the video failed (in fairness, my friend’s technical ability rates on a par with crippled dinosaurs. And I am even worse). The good news is that we got to look at this cigar again to complete the video.

First time, we had two stunners. Mine was the best cigar I have tasted this year and I, if I may skip to the bottom line early, rated it a 99/100. He came in with a more than respectable 96 (we do vary in our assessments, but in general we are not often more than a point or two apart).

The box code was TRU from late 2019, so it would have been fair to make allowances for a very young cigar, but that was not necessary. It was a star.

H. Upmann Sir Winston Cuban cigars

From our second cigars (we are dedicated and thorough), his was even better, with a score of 97-98. Mine, on the other hand, was not. I went 87-88. Now that is not a disaster by any means, but after glories from the first stick, such a letdown.

It shows that this can be a lottery. It also shows how dangerous it can be to rate or review a cigar from a single stick. Sometimes you win the lottery. Other times try again. It would be silly to dismiss a cigar on the basis of one lesser experience.

In fairness to the Sir Winston, the  H. Upmann Sir Winston is normally one of Cuba’s most consistent and finest cigars. My second was that annoying outlier that happens. Not much you can do, except trust your source and buy the best you can. Overall, you’ll do very well.

H. Upmann history

H. Upmann has a long history. In 1844, the Hupmann brothers, Hermann and August, migrated from Britain to Cuba (one has to think that they had originally come from a Germanic country).

They opened the famous H. Upmann cigar factory in Havana. The current factory was once a must-visit, but it is a few years since I was there and there were numerous rumors about what is happening and what will happen to it. But it is centrally located, easy to find, and worth the visit if you are there when it is open.

There are three possible sources for the H. Upmann name – I am referring to the ultimate cigar book for this, Min Ron Nee’s extraordinary An Illustrated Encyclopedia of Post-Revolution Havana Cigars. It might be a little dated now, but for me it is still head and shoulders ahead of any other book on the subject, daylight second.

Upmann may have been a perversion of Hupmann over the years; it may have been named solely after the brother, Hermann; or the “H” may stand for hermanos, Spanish for “brothers.”

The family subsequently opened a bank in Havana, and the cigars became linked. A larger factory was opened. Sadly, the bank failed in 1922 and the factory went bankrupt (Frankau & Co. took it over). Pre-revolution, there were subsequent changes in ownership.

The cigars are world famous and especially popular in the UK.

H. Upmann Sir Winston Cuban cigars

The Sir Winston Churchill connection

Just when the Sir Winston was first produced, no one seems quite certain. But it was definitely pre-1960s.

Even though the producers usurped the great British leader’s name for the cigar, a tribute I have no doubt he loved, his favorite cigar was actually the Romeo y Julieta Churchill (yes, a size/shape of cigar was also named after the man).

However, given that Churchill is estimated to have smoked more than a quarter of a million cigars in his lifetime, I have no doubt he smoked his fair share of Upmanns as the damaged carpets and distraught hostesses in untold British mansions could have attested. He was also reputedly fond of the now-defunct La Aroma de Cuba. Often, he would not finish a cigar, but liked to chew on the end for a while.

Churchill never used a cutter, preferring to poke a hole with a long match specially imported from Canada. He had an ashtray shaped like a small pagoda that traveled with him everywhere. His suits were on an endless loop of repair to fix holes burned by dropped ash.

Cigars were not the only luxury product to benefit from Churchill’s name. His favorite champagne, Pol Roger, named its prestige cuvee after him, though this was only after his death. The first vintage of the Pol Roger Sir Winston Churchill was the 1975, available only in magnum.

Churchill would have loved that also. One of his most famous quotes was, “A magnum is the perfect size for two gentlemen to have over lunch, especially if one isn’t drinking.” He was believed to have enjoyed around 42,000 bottles of Pol Roger during his life, and no doubt many more from other makers. As he also said during the war, “Remember, gentlemen, it’s not just France we are fighting for. It’s champagne.”

Churchill maintained a supply of 4,000 cigars at his home at Chartwell Manor, expensive stuff even in those days. As one of his valets said, “It took me a little while to get used to the fact that in two days his cigar consumption was the equivalent of my weekly salary.”

Churchill first visited Cuba in 1895 during Cuba’s war against the Spanish empire. Thereafter, as he says, Cuba was always on his lips. He also described Cuba as a place where, “Here I might leave my bones.” He did not, of course.

The H. Upmann Sir Winston

H. Upmann’s Sir Winston is in the format known as a Churchill (Julieta), 178 mm in length with a ring gauge of 47 mm.

There is little point in reviewing the outlier, which was muted, never really in balance and just fair.

However, that first Sir Winnie is another thing entirely. Impeccable construction and balance, there was not so much as a hiccup at any stage. Flavors moved and evolved throughout with peanut notes, oodles of creamy coffee, brown sugar, a light dusting of cocoa powder, caramel, cinnamon, and chocolate. Plush, lush and silky, with a magic texture, just cushiony.

As I said, 99 for me. It was a truly glorious cigar and one that should be in every serious cigar lover’s rotation.

These are also cigars that age superbly; you can put a box away today for your unborn child’s twenty-first with confidence. Great stuff!

You may also enjoy:

Pol Roger 2012 Champagnes: Grand Releases For Perhaps The Grandest Vintage

Pol Roger Cuvée Sir Winston Churchill 2006: From A Long And Complex History

Hoyo de Monterrey Escogido Cuban Cigars: The ‘Chosen’ Few

Romeo Y Julieta Tacos Edición Limitada 2018 Cigars: An Old-Fashioned Smoke Built For The Long Haul