Cigars but first a rabbit hole.

You tell me that the guy to the left isn’t a time traveling Matrix character.

I promise cigars.  But here is a close up of the guy to the left of JFK.  This photo is credited as being at Hyannis.

“You hear that, Mr. Anderson? That is the sound of inevitability.”

Ok, I will get back to the central thesis.  But no promises that we don’t circle back.

A number of events coalesced.  First, I have a huge day on Monday that I have been working on for 6 years, and we are all praying that it ends with a cigar.  Then I got this great email from a reader/author here who sent me a link to an article he wrote about cigars here, it was fantastic.  I have been meaning to write about cigars.  Yesterday I had a cigar with a friend who has taken to reading the site and we talked OCBD’s for half an hour, it was fantastic.  It feels like fall, better cigar weather.  And so forth.

I started smoking cigars at 14 with two friends, Todd and Mike, on Sunday afternoons in Rhinebeck NY.  Todd had a driver’s license and a car so we bought Swisher Sweets and drove around and wrote a variety show that would up being a fundraiser for our church.  We called ourselves The Stogie Bros.   That should paint a picture.  In high school I worked pretty much full time so Sunday afternoons were precious and I learned, you spend your precious free time doing that which adds joy.

In my late 20’s I joined The Cigar Club in Greenwich.  I was “sponsored” by a friend I have lost touch with, and we would meet (no more than a dozen of us) at The Greenwich Cigar Store which was owned and operated by Jimmy.  One of us each week had it catered, everyone had their own bottle and we sat either outside on the sidewalk in folding chairs or inside on leather couches, smoked and drank from 7 – 10 every Friday night.  No exceptions and no new members, I was the last.  Never forget – one night we were sitting there and there is a crazy knock on the door.  It is a woman, frantic.  I was the newest and youngest member so I had to get up, I open the door, she pushes in.  “Does anyone here have a plane?  I need a plane.  Does anyone here have a plane,” she said.  She didn’t really ask it, she said it.  So I asked it.  “Why do you need a plane?”

“My gardener was cleaning our greenhouse, he fell through the roof and severed off his arm.  He is at Greenwich Hospital right now but there is a surgeon in North Caroline who can reattach it if we can get him down there now -”

That’s a big ask.  One guy gets up and walks over to the phone while the rest of us watch.  He calls, mumbles, hangs up.  “Go to Westchester Airport, Hangar 17 (I am making that number up) and there will be a plane and a pilot ready for you.”

Those were rarified air times, but the gentleman did give a plane.

Cigars and Ivy go hand in hand because, of course.  Blah blah blah.  Here is a truth about cigars, though, and it is a truth they share with Ivy clothes.  They are authenticators.  Truth serum of character.

Here is a man who smoked cigars, and had the best cigar quote ever in a movie:

Gene Hackman, Crimson Tide. “I don’t trust air I can’t see.”

You can also tell when someone is not telling the truth about cigars.  Demi Moore is attributed with this quote in Cigar Aficianado:   “I like the flavor. I like the taste. I enjoy the smell of a good cigar. It relaxes me. It’s a great social activity, because there’s something about smoking a cigar that feels like a celebration. It’s like a fine wine. There’s a quality, a workmanship, a passion that goes into the making of a fine cigar.”   No you don’t.  Cigars are horrible social activities, unless you are in the company of other cigar smokers.  And it is lazy to call wine “fine” anymore.  I am not saying she doesn’t smoke them, I have no idea, but I am saying that she didn’t say THAT.

It is tough to have a “secret passion” that one claims is a “great social activity.”

Now these, guys, these guys smoke cigars. 


I know, Einstein smoked a pipe too.  And I am not sure why Freud is twerking.  But I do know this, they are authentic cigar smokers.  That always adds to the experience for me.  When I am nervous, I light a cigar.  When I am relaxing, I light a cigar.  The people I associate with who smoke cigars really smoke a cigar.  There is an intention to the lifestyle that I really admire.  As opposed to people who use cigars as props.  Cigar Cosplay.

Gregory Hines PAID to have pictures of himself taken with cigars. That is IVY.

Finally, my all time favorite aspect of cigar smoking.  When one is deliberate about letting others know they are doing it, they are enjoying it, and they won something, even if it is just a day.

Penn beats Harvard, back in ’12 but a win is a win.

11 Comments on "Cigars but first a rabbit hole."

  1. I love that picture of Chens dressed up like Freud!

  2. But did the gardener get his arm back?

  3. Swisher Sweets were great in high school.

  4. Jesse Livermore | September 24, 2021 at 12:55 pm |

    Sometimes a cigar is just a smoke.

  5. I enjoyed going to A Little Taste of Cuba in Princeton when I was younger. I also visited the Carnegie Club in New York from time to time after work. Cigars were a nice way of enjoying a social ritual without the direct risk of lung cancer (though I knew there are other cancer risks associated with cigars). I still disliked the residual smell but didn’t have much need to dry clean the clothes I wore. Once I discovered pipes, however, I stopped smoking cigars altogether; I found it easier to sample different tobaccos and limit what I had in one sitting.

    Eventually I gave it all up; the smell, health risks, and what became a sizable dry-cleaning bill did it. Upon honest reflection, however, I do miss the ritual sometimes – even if I can’t accept the downsides anymore.

  6. On the golf course, deep sea fishing and around the campfire with friends.


  7. They always taste best to me in warm and humid locations. My love affair began with Royal Jamaicans back in 76. My humidor is lightly stocked these days with the very best. At this stage in life, if I’m going to have a smoke why waste it on a lesser quality product? Go big or…. 👍🏻

  8. And here, gentlemen, are Bruce Boyer’s articles that appeared in The Cigar Aficionado:

  9. Camelot bards recount JFK sending the man in the Matrix glasses to Cuba just prior to the signing of a certain embargo. He returned with a load of soon to be contraband.

  10. Marshall Baird | September 28, 2021 at 12:12 am |

    Do I still have to look at Gregory Hines every time I open Ivy Style? Poor guy really thinks he’s cool. Pitiable.

    Oh sir, Gregory Hines is cool. – JB

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