Winston Churchill

Winston Churchill is an iconic leader who was well known for always having a cigar in his mouth. Probably well after the cigar had been smoked down to the nub. Which who can blame him, the stress from the war must have been crazy.
Winstons Favorite Cigar:
- Romeo y Julieta
Winstons Favorite Pairing:
- A glass of Brandy (or two)
Like most of us can probably relate, theres nothing better than getting home from a long day at work and sitting down to a nice delecate glass of something that punches us in the face. On the rocks of course, just to remind us that the work is never done. Oh yeah and pairing that with a beautifully crafted cigar.
So, next time you feel the weight of the world on your shoulders, channel a bit of Churchill’s swagger. Grab a Romeo y Julieta, pour yourself some brandy, and remember, every puff is a testament to forging ahead, no matter what.
Ernest Hemingway
Ernest Hemingway didn’t just write adventure stories he lived for the adventure. Whether in Paris, Key West, or a dusty street in Havana, cigars were always part of his story. That creative mind paired with a fine Cuban Montecristo was a force to reckon with. I wander if the cigar gave him super writing powers?
Hemingways Favorite Cigar Brand:
- Montecristo
Hemingways Favorite Cigar Pairing:
- A glass of Rum
So, if you’re looking to channel a bit of Hemingway’s genius, take up a Montecristo after a long day. Pair it with a glass of something robust, and let your thoughts wander to literary creativity. You might not pen prize-winning novels, but you’ll definitely enjoy the journey.
John F. Kennedy

John F. Kennedy had a thing for cigars. Before signing the embargo against Cuba, he made sure his aide had secured a hefty stash of H. Upmann cigars. It was a clever move, showcasing political acumen mixed with personal indulgence.
Kennedys Favorite Cigar Brand:
- H. Upmann cigars
Kennedys Favorite Cigar Pairing:
- Politics
Feeling a bit presidential? Step into JFK’s shoes with the classic touch. Enjoy an H. Upmann and imagine the blend of tradition and modern thinking in every draw.
Sigmund Freud
Sigmund Freud was a thoughtful man with a cigar in hand. The man who unraveled the mysteries of the mind enjoyed an excellent cigar.
Freuds Cigar:
- Vienna-crafted Trabuco cigars
Freuds Favorite Pairing:
- Coffee
The psychoanalyst once famously quipped, “Sometimes a cigar is just a cigar.” This statement was more than just a witty retort. It hinted at his ability to see complexities without overcomplicating every detail. For Freud, cigars were perhaps a moment of simplicity amidst a world of intricate thoughts.
life have you stressed? Channel your inner Freud. Take a moment with a fine cigar, maybe a Trabuco if you can find one, and unwind with a coffee. Let your mind wander freely, and you might find clarity in the most expected or unexpected places.
Groucho Marx

Groucho Marx, with his signature glasses and exaggerated mustache, had cigars that became part of his comedic genius. Every flick of the ash or puff of smoke was like a punchline, bringing that extra flair to his routine.
Groucho Marx Favorite Cigar:
- La Palina cigars.
Groucho Marx Favorite Pairing:
- Comedy
Craving a bit of old-school humor with a touch of class? Spark up a La Palina, channel Groucho’s spirit, and film your own bit, if you dare. I can’t promise you will get famous however, you’ll sure have the props to get started.