Even if you’re not a smoker, you probably know that Cuban cigars are the cream of the crop when it comes to stogies. Maybe it’s got something to do with the iconic images of former world leaders like Fidel Castro and Sir Winston Churchill puffing on cigars while in the throes of diplomatic crises. Or perhaps it’s how difficult these highly prized cigars can be to find. But how exactly did the tiny Caribbean nation of Cuba become known as the world’s foremost cigar producer, and why are Cuban cigars so rare? 

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THE HISTORY 

If you believe expert historians, the Mayans were the first to roll dried tobacco in plantain leaves and create the cigar—for medicinal purposes and religious ceremonies, of course. When Christopher Columbus showed up in the 15th century, he and his sailors took to smoking stogies, then took the production techniques and tobacco plants (called “cohiba”) back to Spain, and made cigars popular across Europe.  

For a long time, Spain maintained its hold on Cuban tobacco and cigar production, making massive profits and banning Cuba from creating its own cheroots. When, in the 18th century, it was discovered that finished cigars were better at surviving the transatlantic journey than tobacco leaves, Spain eased its hold. In the early 1800s, Cuba got its first commercial cigar factory and by 1810, Cuban cigar brands began registering their own trademarks.  

After the Cuban revolution, the cigar industry went through some turbulence as it was nationalised but survived with help from the Soviet Union. After a brief golden age, the industry suffered another setback thanks to bad weather, shortages of fuel and fertiliser, failed production schemes, and a shortage of knowledgeable staff.  

Since 2002 though, Cuba’s torcedores (cigar rollers) have embraced traditional techniques and revived the quality of their cigars, driving increased demand and higher prices.  

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WHAT MAKES THEM SPECIAL? 

For starters, the torcedores have had centuries to perfect their cigar-making techniques. Then there’s the fact that these stogies are made with only the highest-quality materials—including 100% Cuban tobacco—and laser-like attention to detail. In fact, it’s rumoured that there are over 100 steps to produce a true Cuban. Add the fact that the government heavily regulates the industry to ensure that every cigar is perfect, and you begin to understand why Cubans have attained such rarefied status.  

The final key to the puzzle is, of course, how rare real Cubans are outside the island. Thanks to the American embargo—in place since the 1960s—commercial imports into the US are banned (though you can sneak a few in your suitcase if you manage to take a holiday there). Even further afield, fakes are as common as the real deal.     

With such history and cachet, it’s no surprise that Cuban cigars find fans everywhere. Here are some of the world’s most famous cigar smokers and their favourite roll-ups. 

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FIDEL CASTRO

Arguably the world’s most iconic cigar smoker, the former Cuban leader was almost single-handedly responsible for boosting Cuba’s cigar industry and its image on the world stage. Case in point? He played a big role in Cohiba, one of the most famous Cuban cigar brands, and harboured a decided preference for Cohiba Corona Especiales. 

JAY-Z 

The king of rap loves a good cigar, especially if they’re from Cuba. He’s a fan of Ramon Allones and Montecristo, but he also has his own cigar production plant and team at Cohiba, where he produces the Comadors. 

RIHANNA 

The Grammy-winning Barbadian singer appreciates the finer things in life, and that includes cigars. Her favourites include mentor Jay-Z’s Cohiba Comadors, though in her video for “Can’t Remember to Forget You,’ she puffs on several different brands. 

SIR WINSTON CHURCHILL

Another iconic cigar aficionado, the former British Prime Minister cultivated his love of cigars while stationed in Cuba as an officer and later stockpiled nearly 4,000 cigars at his home in Chartwell. His favourites? The Montecristo No.2 and Romeo Y Julieta. 

MICHAEL JORDAN

The basketball legend began smoking cigars in 1991 and was known to light one up to calm his nerves before a big game. He’s particularly partial to the Partagas Lusitania.