A Cigar Adventure: a Visit to Up Down Cigars and a PCA Event in Chicago

I did something wild this week, for me at least.  I attended the Premium Cigar Association‘s Democratic National Convention event at Up Down Cigars in Chicago, IL.  I I made the whole trip within a 24 hour window.  Here’s how it went down:  I flew from Philly to O’Hare on Tuesday, arriving in Chicago around 1PM local time.  I walked about 22 miles from the gate to the train that would take me, eventually, to the Blue Line train into the city.  The “L” train stop was about 2 miles from the shop, so instead of trying to take a bus, I figured I had time to hoof it. Said bus passed me several times. Anyway, I got to Up Down Cigars around 3:30 for the 6:00 PCA event.  Rats, I’ll have to hang around a cigar shop for a couple hours.  The staff at this shop is quite knowledgeable and attentive, it’s not a large shop, cabinet humidors around the perimeter (actually fronts for the walk in behind it where the backstock is stored), with some cabinets here and there with accessories, pipes and humidors.  It’s rather cramped, by suburban store standards, but fairly typical for a city shop with a long history (The original owner, Diana Silvius, is a legend in the cigar business. Phil Ledbetter is the current owner, an instantly likable guy).  I perused the humidors looking for something to fill the time.  I was directed to a store exclusive, the Fausto 10/50.  

I’m going to pause here to talk about the cigar, the Fausto 10/50.  This was made for the 50th anniversary of the shop back in 2013, which was also Tatuaje Cigar‘s 10th anniversary.  This is a 6 3/8″ x 42 lonsdale, with an Ecuador Habano Maduro wrapper, and Nicaraguan binder and fillers, made at the My Father Factory in Esteli.  This is an exceptional cigar, I smoked two this week, one a the shop and one when I got home.  Smaller ring cigars need to be smoked slowly, this is one to be savored, first because over drawing it will make it burn hot and ruin it, second because it has some strength, and in the case of the one I smoked at the shop, I was pacing myself because it had already been a long day and I had a long night ahead of me.  It’s a heavy cigar with cocoa and some spice, an absolute bargain at $10.50, although with applicable Chicago taxes it was more like $13.75.  I really like the Fausto line, and this was a really good version. I bought 3, smoked two, have one left to savor at a future time!

Back to the trip.  Shortly after I arrived at the shop, Boston Jimmie of Stogie Press showed up and we hung out until the event at 6.  The PCA hosted events at both political conventions, I was unable to attend the one in Milwaukee for the RNC.  The event was held in the patio area behind the store, a maybe 30′ x 50′ tented area. Drew Estate was the cigar sponsor, so I had a Liga Privada No. 9 while there, although there were many choices available.  Ben Pearson, the area rep was there.  I finally met Josh Habursky who was recently appointed Executive Director after Scott Pearce left to head the Cigar Association of America. Scott was there as well and I had a chance to talk to him a bit.  I also got to hang out with my friend Luigi Lucente, the man behind the Cigar Medics Humidimeter, The Baller cigar cutter, and the Guillotina de Saka cigar cutter, among other

Photo Courtesy of Boston Jimmie

clever cigar accessories. I imagine there were somewhere around 100 people there.  It was a nice event with various hors d’oeuvres, wine, beer and liquor.  After the event Luigi dropped me at the train and I made my way back to O’Hare to await my 6am flight.  

They had issued something like 350 free tickets for this event with a waiting list of 200.  If everyone had showed up it would have been a disaster.  It occurs to me that they should have put a nominal fee on the tickets, which would incentivise people to attend if they really wanted to, and raise some money for the association.  I don’t know that any of the Democratic legislators who are key to the cigar industry fight against taxation and regulation were there, I have to think that holding it during the convention hours (and the convention center was 7 miles away, which might take 2 hours in Chicago traffic!) might have deterred their attendance.  It was a nice event, I’m glad I put myself through what I did to attend, but I can see how it could have been better.  I understand that the Milwaukee event was more elaborate, given the way many in the cigar industry lean politically, I can see where more might have gone into that one.  Anyway, good event, great people and a really nice shop. I discovered that walking through a deserted O’Hare was surreal, and I’m too old for pulling all nighters!

That’s all for today, until the next time, 

CigarCraig