Quintessentially recently had the chance to meet up with Wingtip’s in-house tobacconist, Karl Theobald, to understand why the art of cigar-smoking is such a sensory experience.
 

Quintessentially: How long have you been smoking cigars? Do you remember your first one?


Karl Theobald: “I smoked my first cigar at age 20 while at UCLA. My friend had returned from Europe with a pack of Cuban Punch mini cigarillos and we smoked a couple. I got a huge buzz off those little minis. Then I didn't smoke another cigar until I was 25 and music directing a circus here in San Francisco. A regular customer always brought cigars to hand out and I wound up with a couple. The piano player on the show, when he saw what I was smoking, told me they were terrible cigars. I had no idea. The next day he brought me a Cuban Trinidad Fundadores, the cigar that changed my life. For the next several years, I went to as many cigar shops as possible, talking to as many cigar makers as possible, smoking as many different cigars as my budget allowed and making as many friends in the small Bay Area cigar community as I could. One of those friends recommended me to the Wingtip people when the job became available three years ago.”
 

Is there a cigar you prefer above all others?

“I have no favourite cigar, although I do love those that are spice-forward, creamy, complex, with hints of chocolate in the finish. I also love almost everything that comes from Tatuaje, My Father, the Placencia factory, the Eiroa Factory and Jochy Blanco's factory in the Dominican Republic.”
 

What makes a good cigar?

“When thought goes into the blend with the intention of making something special, as opposed to simply developing a new skew for their company, that’s when the magic happens.”
 

What’s unique about the experience of shopping for cigars at Wingtip with you?

“Cigar shoppers will find that I ask them questions no tobacconist has asked them before. Their experience is important to me and I take pride in recommending the perfect smoke for their event, drink, meal or break from work.”
 

Is there a Wingtip memory or event that you particularly relish?

“Honestly, every day at Wingtip is memorable. Getting to know the members and the staff - who are all amazing - has been incredible. The members are so generous, fun and kind. The first single memory that comes to mind though is after one of the big member parties when the entire staff and several of the die-hard members were smoking and drinking way after the party had ended. The chef just brought some snacks out that he decided to whip up at the spur of the moment. That was a great night.”
 

Do you have any advice for a novice cigar smoker? 

“For someone just getting into cigar smoking I'd suggest starting on the lighter side with something from the Dominican Republic. Tobacco from the D.R. typically has less nicotine and will be less likely to give you a big head buzz or upset your stomach.Once your body is used to that sensation, though, smoke everything you can get your hands on. There are so many different flavour profiles, body intensities, sizes, shapes and complexities. The more I learn, the more I realise I need to learn. It's never ending. Once you find a brand you like, ask your local tobacconist what else they recommend that's like that brand, or that specific cigar. Any good cigar shop should be able to show you several other things you'd probably love.”
 

Explain a pairing that stands out for you…

“In terms of pairings, it really depends on the individual palate. I'm a huge fan of bourbon with a spicy Nicaraguan cigar. But I've been seen drinking wine, tequila, rum, scotch, mezcal or gin. It depends on the body, flavour profile and strength of the cigar. Chocolate is usually pretty amazing as well.”


For information on Karl Theobald’s unique cigar service, please get in touch with your lifestyle manager.