Famous Cigar Smokers Throughout History

Winston Churchill smoked an estimated 250,000 cigars during his lifetime — roughly 8-10 per day for over 60 years. His brand of choice was Romeo y Julieta, and he had a custom size created for him (the Churchill vitola, 7 inches × 48 ring gauge, now an industry standard). But Churchill is just the most photographed member of a long line of cigar-obsessed figures who shaped how the world sees cigar culture.

Political Leaders

Winston Churchill (1874-1965)

Churchill discovered Cuban cigars during a visit to Havana in 1895 as a young war correspondent. He was rarely photographed without one. During WWII, he required a constant supply — special arrangements ensured Cuban cigars reached him despite wartime shipping disruptions. His favorites: Romeo y Julieta, Camacho (then known as La Aroma de Cuba), and various custom-rolled Cubans. The Churchill vitola (7" × 48) was named in his honor and remains one of the most popular sizes worldwide.

John F. Kennedy (1917-1963)

The night before signing the Cuban Embargo in February 1962, Kennedy allegedly sent his press secretary Pierre Salinger to buy every H. Upmann Petit Corona in Washington. Salinger returned with 1,200 cigars. The next morning, Kennedy signed the trade embargo that would make those same cigars illegal to purchase in the US. Whether the story is perfectly accurate or embellished over decades, it captures how seriously cigar smokers — even presidents — took their supply chain.

Fidel Castro (1926-2016)

The irony of Cuba's most famous leader being a cigar icon isn't lost on anyone. Castro smoked Cohiba Lanceros — a brand originally created exclusively for him and Cuban diplomats in the 1960s before becoming commercially available in 1982. He reportedly quit smoking in 1985 for health reasons and public image, though some accounts suggest he continued privately. Cohiba remains Cuba's most prestigious brand.

Ulysses S. Grant (1822-1885)

After his victory at Fort Donelson in 1862, newspapers reported Grant smoking a cigar during the battle. Admirers sent him over 10,000 cigars in response. This turned a casual smoker into a dedicated one — Grant reportedly smoked 20+ cigars daily for the rest of his life, eventually dying of throat cancer. His wartime images with a cigar became iconic Civil War photography.

Entertainment and Arts

Groucho Marx (1890-1977)

Marx's cigar was a comedy prop as much as a habit — he used it for timing, punctuation, and physical comedy. He'd hold it while delivering a punchline, tap ash for emphasis, or use it to point accusingly at his straight man. He preferred inexpensive domestic cigars and was known to smoke anything available, treating the cigar as a performance tool rather than a luxury indulgence.

George Burns (1896-1996)

Burns smoked El Producto Queens — a budget machine-made cigar — for most of his 100-year life. He estimated he smoked 10-15 per day and credited them (jokingly) with his longevity. Like Groucho, his cigar was integral to his comedic persona — a prop that gave him something to do with his hands and natural pauses in delivery.

Mark Twain (1835-1910)

Twain claimed to smoke 22 cigars per day (likely exaggerated in his characteristic style) and was famously cheap about it — he preferred 5-cent domestic cigars and openly mocked expensive imports. His quote: "If I cannot smoke in heaven, then I shall not go" summarizes his relationship with the habit. He also wrote extensively about tobacco in his essays.

Arnold Schwarzenegger

Schwarzenegger is perhaps the most visible modern cigar advocate — photographed smoking Padrón and Cohiba cigars regularly, he's been open about the habit throughout his career as actor, governor, and public figure. He launched the cigar dinner concept in Hollywood and remained a cigar smoker even during his governorship (famously setting up a smoking tent outside the California Capitol since the building was smoke-free).

Business and Sports

Michael Jordan

Jordan's post-championship cigar celebrations became iconic imagery of the 1990s Bulls dynasty. Beyond celebrations, he's a dedicated daily smoker who gravitates toward Cuban cigars (Partagás, Hoyo de Monterrey) and has his own private humidor facilities. His influence helped normalize cigar smoking among professional athletes during the 1990s cigar boom.

Jack Nicklaus

Golf and cigars share a natural connection — the pace of a round matches a cigar's burn time. Nicklaus smoked throughout his career and helped establish the golf-course-cigar tradition. Many modern golfers (including occasional tournament winners lighting up on the 18th green) follow in his tradition.

J.P. Morgan (1837-1913)

The financier reportedly spent over $5,000 annually on Havana cigars — an extraordinary sum in the early 1900s (equivalent to $150,000+ today). He smoked large, custom-rolled Cubans and was photographed with cigars in nearly every portrait. His consumption symbolized Gilded Age excess and helped establish cigars as a marker of financial success.

The Cigar as Symbol

What connects Churchill, Marx, Jordan, and Twain isn't taste in tobacco — it's the cigar's dual function as both personal pleasure and public statement. A cigar says something. Whether that message is power (Churchill during the Blitz), humor (Groucho's timing device), celebration (Jordan's championships), or defiance (Twain's anti-establishment cheapness) depends on the smoker.

The 1990s cigar boom — driven partly by celebrity adoption — created a new wave of famous smokers. But the tradition stretches back centuries. Columbus's crew observed indigenous Cubans smoking rolled tobacco leaves in 1492, and within decades, European aristocracy had adopted the habit. Every generation since has produced its iconic cigar figures.

For the broader history, see our piece on Cuban cigar history from Columbus to the embargo. And for the economic boom that celebrity endorsement triggered: the 1990s cigar boom explained.

Political Leaders and Cigars

Beyond Churchill, numerous political figures maintained notable cigar habits. John F. Kennedy famously ordered 1,200 Cuban Petit Upmanns the day before signing the Cuban embargo in 1962, securing his personal supply before the ban he himself was enacting. Ulysses S. Grant smoked 20 cigars daily during the Civil War, receiving thousands of boxes as gifts from supporters after his victories at Vicksburg and Appomattox. Fidel Castro smoked Cohiba Lanceros for decades before publicly quitting in 1985, though associates reported he continued privately for years afterward.

Modern political cigar culture is more discreet due to public health messaging, but cigar dinners remain standard fundraising events for both American political parties. The Cigar Rights of America organization actively lobbies against tobacco taxation and regulation, maintaining relationships with sympathetic legislators who understand the difference between premium cigars and mass-market tobacco products in both manufacturing quality and usage patterns.

Entertainment Industry Influence

Hollywood's relationship with cigars has fluctuated across decades. Golden Age actors like Groucho Marx and George Burns made cigars central to their personas. The 1990s brought Michael Jordan, Arnold Schwarzenegger, and Jack Nicholson to Cigar Aficionado covers, associating cigars with athletic success, physical power, and cultural sophistication simultaneously. Modern celebrities including Jay-Z, Matt Damon, and LeBron James maintain visible cigar habits that influence younger generations of potential enthusiasts.

The entertainment industry's cigar influence extends beyond individual celebrity to content creation. Television shows like Mad Men and Boardwalk Empire normalized period-accurate cigar smoking on screen. Podcasts and YouTube channels dedicated to cigar reviews have created a new category of cigar celebrity where knowledgeable reviewers build audiences rivaling traditional media. This democratization of cigar culture through digital content has replaced the top-down magazine model of the 1990s with grassroots community-driven enthusiasm accessible to anyone with internet access and curiosity about the hobby.