YOU GOTTA TRY THIS- How to smoke a cigar like a fucking gentleman.

Large5/09/2025 7:30 PM

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I know a lot of people who smoke cigars, and a good number of those people look like fucking idiots when they do.

I am not trying to be "Miss Manners" here, judging what should be a non-judgmental hobby/vice. Still, there are a couple of intricacies to enjoying a good stick that would benefit anyone who wants to smoke a cigar for the purpose of more than just looking good on a social media post or never-aired Gatorade commercial.

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Since I am not an expert in the fine art of cigars, I invited a gentleman (whose name is Tom, but that's not important) from a small company outside of Chicago that makes one of my current favorite cigars… the "Il Piccolo" from NEVERASH.

Tom and I broke down the whole process of getting the most out of what you're smoking, including…

How to choose a cigar.
How and where are they made.
The different ring sizes and lengths.
How to light it properly.
When should the band be removed.
How much ash should you leave at the tip.
What to pair with a good cigar.
How much of a cigar you should smoke.
And even how to put it out once you're finished.

We also did a little history segment, where I mentioned the time JFK (who was an avid smoker of Petit Upmanns) ordered his press secretary, Pierre Salinger, to round up one thousand of his favorite Cubans in twenty-four hours. It was short notice, but the president had his reasons, considering he was in the process of signing an embargo that would prevent any products from Cuba from entering the United States.

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Fortunately, Sallinger was able to fill the order on time and managed to find a total of 1,200 cigars. Once the president had his stash, he signed off on the embargo, Cuba was cut off, and Kennedy was able to enjoy a post-coital smoke after raw-dogging the living shit out of Marilyn Monroe… Allegedly.

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The whole episode will be lost on people who will never have a real cigar game and/or elevate their existing game past what you can buy at the bodega. But for everyone else, it might be worth a listen.

So, if you're on the golf course…