Famous Cigars, Smokers and Unbelievable Facts: Unique Stories from the World of Cigars

Cigars aren’t just about craftsmanship—they’re about culture, character, and often, legacy. Throughout history, political leaders, authors, entertainers, and even psychologists have turned to cigars as symbols of relaxation, intellect, indulgence, or rebellion. Many of them had personal favorites, unique habits, and even shaped the cigar industry itself through their visibility and influence.

Here’s a deeper look at the famous cigars, smokers, and the unexpected stories that define the rich tapestry of cigar history.

Famous Smokers & the Cigars They Made Famous:

Cohiba – Castro’s Private Reserve

Few cigar brands carry the mystique of Cohiba, which was created in 1969 specifically for Fidel Castro and high-ranking Cuban officials. Originally blended by Eduardo Rivera, the cigars were rolled in secret at El Laguito factory in Havana and distributed in unbanded boxes to Castro. It wasn’t until 1982 that Cohibas became available to the public, introduced during the World Cup in Spain. Known for their rich, full-bodied profile, Cohibas remain a symbol of Cuban excellence. Castro himself favored the Cohiba Lancero, a long, elegant vitola that became iconic in photographs. SHOP COHIBA CIGARS SOLD IN THE STATES

Ulysses S. Grant – War, Presidency, and 20 Cigars a Day

General Grant became a symbol of determination during the Civil War—and a symbol of cigar devotion. After word spread that he smoked a cigar during a key battlefield victory, Americans began sending him thousands of cigars in appreciation. At the height of the war, Grant reportedly smoked up to 20 cigars a day, and continued the habit through his presidency. While records don’t name a specific brand, it’s believed he smoked strong, full-bodied cigars, often gifted or locally available during the era. His smoking was so visible that political cartoons of the time frequently depicted him with a cigar clenched in his teeth.

Mark Twain – A Humorist’s Fiery Habit

Samuel Clemens, better known as Mark Twain, had a cigar habit as large as his literary legacy. He famously smoked between 20 and 40 cigars a day, mostly inexpensive, locally rolled cigars in bulk—believing the cheaper smokes were actually less harsh. He once gave up cigars to appease his wife but claimed he became too ill without them and promptly resumed his routine. Twain favored Connecticut broadleaf-wrapped cigars, though he was never too particular—as long as they were plentiful. His classic quote: “If smoking is not allowed in heaven, I shall not go,” remains one of the most famous cigar lines in history.

Winston Churchill – The Original Namesake

One of the most iconic cigar smokers of all time, Winston Churchill was rarely seen without a cigar. He reportedly smoked 8 to 10 cigars a day, often during meetings, meals, and speeches. His favorite was the Cuban Romeo y Julieta, particularly the Churchill-sized vitola—a long, robust smoke that now bears his name. He also enjoyed La Aroma de Cuba, a lesser-known Cuban brand at the time. Churchill’s name became so synonymous with cigars that “Churchill” is now a widely used size in the cigar world (7 x 47).

John F. Kennedy – One Last Cigar Run

Before signing the embargo against Cuba in 1962, President John F. Kennedy famously instructed his press secretary, Pierre Salinger, to purchase as many of his favorite Cuban cigars as possible. Salinger returned with 1,200 H. Upmann Petit Coronas, after which Kennedy signed the trade ban, cutting off all legal access to Cuban cigars for Americans. It’s a legendary moment in cigar lore that underscores just how much Kennedy loved his smokes.

Ernie Kovacs – Cigar Humor and Commercial Genius

Television pioneer Ernie Kovacs wasn’t just a cigar smoker—he built them into his persona. He reportedly smoked 20 Cuban double coronas a day, especially while working on scripts or rehearsing. He and his wife, Edie Adams, created unforgettable commercials for Dutch Masters and Muriel cigars, often blending dry wit with surreal visuals. While specific brands changed over the years, Kovacs had a fondness for larger ring-gauge Cubans, appreciating their flavor and longevity.

Sigmund Freud – A Theorist with a Cigar Always in Hand

The father of psychoanalysis, Sigmund Freud, was known for his intense daily cigar routine. He smoked up to 20 cigars a day, despite developing oral cancer later in life. Freud believed cigars helped him concentrate and once dismissed psychoanalytic speculation about his habit with the famous line, “Sometimes a cigar is just a cigar.” His favorite cigars were reportedly Austrian and German-made, particularly Don Pedro and Reichstag, which were milder and more floral than modern Nicaraguan or Cuban styles.

Michael Jordan – A Modern Icon with a Refined Palate

Basketball legend Michael Jordan is one of the most influential cigar smokers of the modern era. He smokes at least one cigar a day, often on the golf course or while relaxing at home. Jordan has publicly expressed his love for Cohiba, Partagás Lusitania, and Hoyo de Monterrey Double Coronas, favoring large-format Cuban cigars with balance and complexity. He’s also a fan of Dominican blends like Fuente Fuente OpusX and La Flor Dominicana. Jordan’s presence has helped bring cigars into pop culture, making them symbols of celebration and personal luxury.

Other cigar fun facts...

What is the Most Expensive Cigar in the World?

The Gurkha Royal Courtesan – A Cigar Worth a Fortune

The most expensive cigar in the world, the Gurkha Royal Courtesan, carries a staggering price tag of $1.36 million per cigar. Made with Himalayan tobacco infused with Louis XIII Cognac, the cigar is wrapped in gold leaf, features diamond-encrusted bands, and is hand-rolled by a blindfolded master roller to enhance tactile sensitivity. It’s more statement than smoke—but a testament to how far the cigar world can stretch into the realm of luxury.

What is the Oldest Cigar in the World?

Mayan Cigars and 600-Year-Old Smoke

In 2012, archaeologists discovered ancient Mayan cigars in a sealed clay pot in Guatemala. Amazingly preserved thanks to airtight conditions, the cigars are believed to be over 600 years old and marked with glyphs indicating they were gifts for elite rulers. Though unsmoked, they remain one of the oldest intact cigars ever found—proof that tobacco’s ceremonial and cultural legacy goes back centuries.

Timeless Appeal of Cigars

From the battlefields of the Civil War to the back rooms of political power, from literary salons to sports arenas, cigars have left their mark on history through the people who smoked them. Each story adds another layer to the timeless appeal of cigars—more than a luxury, they are a ritual, a symbol, and in many cases, a signature of the person behind the smoke.

Whether you’re puffing on a budget bundle or savoring a top-shelf treasure, remember: you’re part of a global tradition filled with characters, craft, and a whole lot of personality.

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