I could tell you about what it was like writing about the news that STG was purchasing Alec Bradley on my phone while taxing to take off for Las Vegas on Wednesday morning.

I could give you some feedback about what companies are saying during the first day of the Total Product Expo (TPE) trade show.

I could talk about how the current scheduling conflict of TPE 2023 and Procigar 2023 taking place during the same time. I could talk about the potential 2024 schedule when the PCA Convention & Trade Show is rumored to take place in April.

But instead, I’m going to talk about Sergio.

In the corner of J.C. Newman’s TPE 2023 trade show booth is this poster of Sergio Montolfo, the late evp of operations for Phillips & King who passed away less than a month ago. Phillips & King is a large California-based tobacco distributor owned by Kretek, which also owns TPE, the trade show we are currently in Las Vegas to cover.

I despise when people are all of a sudden best friends with the recently-deceased. Unlike a lot of the people at TPE 2023, I had probably only a few dozen interactions with Sergio over the last decade, most of them were at various TPE trade shows. There’s only one I distinctly remember, it’s the time I met Sergio for the first time.

The first TPE trade show I attended was 2017. TPE asked me to be on a panel alongside executives from premium cigar companies to talk about how TPE’s then-target audience—tobacco outlets, convenience stores, etc.—could sell premium cigars. Tommy Chong—yes, that Tommy Chong—was TPE’s keynote speaker and spoke before our panel, I believe the start time of the keynote from one half of Cheech & Chong was 8:00 a.m. I wasn’t surprised to see the room half full. But by the end, the room was full and it oddly stayed that way by the time we got on stage.

At this point, there were very few premium cigar companies at TPE, more than a quarter of them were represented on this five-person panel. TPE was a lot smaller, CBD was just starting to enter the mainstream—Chong was there to promote a licensed CBD product—and for cigar people, TPE wasn’t too far removed from being easily confused with the now-defunct NATO trade show.

I met Sergio, at least in earnest, at that 2017 TPE trade show. He wanted to help me. I don’t know what he was trying to help with—in complete contrast to TPE 2023, there wasn’t much for me to write about at TPE 2017—but he wanted to be helpful. At some point I found myself in the P&K booth—or perhaps it was called the Kretek booth—and was sitting at a long table butted up against another table where Sergio was meeting with a customer. After finishing my meeting with P&K, I didn’t have much else to do, so I just sat there, finished my cigar and eavesdropped on Sergio Montolfo working for his customer’s business—business that could not have been worth his time—in a way that remains unrivaled to this day.

If memory serves correct, the total size of the deal was less than $15,000 after discounts. The customer was attempting to stack various promotions from Altadis U.S.A., Drew Estate, Rocky Patel, General Cigar Co. and others, along with deals P&K was offering into one larger order through P&K. The customer wanted a combination of discounts and free goods—two countertop cabinet humidors from either Altadis or General were a sticking point—that were explicitly not supposed to be combined into one deal. Further complicating the matter was the fact that he wanted to be able to redeem a promotion General Cigar Co. was running if you placed order through General by buying the products through P&K.

By the time my meeting had started, it was apparent that Montolfo’s meeting had already gone off the rails. But Sergio was going to work for this business. Long after my meeting ended—I had been at the neighboring table for more than hour—the deal was getting serious. The customer was calling someone else involved in the store, Sergio was visibly sweating, and whatever paper deal sheet was on the table had so many things crossed and out in rewritten, I’m not really sure what utility it served.

Sergio asked if I needed anything. Did I want a water or a beer or a cigar? I should have asked for one of those humidors, but I had more or less just met Sergio. At this point, I was not only interested in learning about P&K and its customers but I was also invested in the outcome of this deal like a fan watching a back-and-forth football game.

If what the customer told Sergio was true—that Altadis and Rocky Patel had said they were willing to do the free goods so long as P&K would sign off—and Sergio could get General(?) to negotiate on getting not one, but two humidors—would the guy agree to the deal? The customer said yes.

Sergio got up, walked to the General(?) booth, and came back a few minutes later.

General agreed, but now the customer needed to have the products shipped at different times because too many cigars were going to be heading to stores all at once and I guess those promotional countertop cabinet humidors weren’t going to hold these cigars.

Sergio Montolfo stood up again, moved his chair a few feet away from the table, turned 180 degrees and sat back down with his back facing the customer.

“(customer’s name), if you want to fuck me, let’s get it over with right now,” he said in a joking but clearly frustrated manner.

Well, clearly frustrated to me, the customer seemed indifferent to the choreography and accompanying dialogue; he really was concerned what happened if those cigars all showed up at once.

Sergio then apologized to me for being unprofessional. (Less than 100 yards away was a booth with a live alpaca that had defecated in an aisle on the trade show floor earlier which meant that now anytime the alpaca was moved on the trade show floor there was one person dedicated to cleaning up the mess that was made. I could not make this up.)  I certainly didn’t need to be apologized to, to this day I’ve never seen someone go so out of their way to make a sale that I’m guessing was inconsequential for Sergio’s week, let alone for Sergio’s year.

You’d be wrong to assume that my future interactions with Sergio were crude. They were anything but. We would joke about that interaction in 2017, it remains a vivid memory for me all these years and trade shows later. In what was undoubtedly fewer than 50 interactions with Sergio over the course of the next five years, he was always kind, always asking how he could help me or halfwheel.

To J.C. Newman’s thoughtful point, TPE was as much Sergio’s trade show as it was anyone else’s. At a time when cigar companies were exhibiting at this trade show mostly as a favor to P&K and the large volume of business that P&K does, one of the reasons why Cory Bappert, president of Oliva, or Rocky Patel, the man himself, was at this trade show was because of Sergio. Would these people have shown up if P&K wasn’t a large customer? Absolutely not. Would these people have still shown up if Sergio wasn’t as nice as he was? I’m not so sure. What I do know is that Sergio made that era of TPE far more enjoyable.

That day, Sergio spent probably more than two hours chasing that Rube Goldberg machine of a transaction. He physically got out of his seat to go walk across the (smaller) trade show floor to get a company to sign off on a promotion in exchange for this random retailer buying less than $1,000 worth of cigars from this company and then again and again.

After Sergio eventually reversed himself back to a conventional seating position, he and the retailer got to the brass tacks of the matter. Eventually, the deal was closed, though I wouldn’t be surprised to have later learned that the retailer showed back up 30 minutes later to try to get some free t-shirts.

I don’t want to demean a five-figure order of cigars, it’s not a small number, but I’ve never seen someone work that hard for a sale so seemingly inconsequential. I don’t know if Sergio needed that sale to hit a sales target, I don’t know if the customer’s account was otherwise worth $250,000 per year to P&K, I don’t know if Sergio was just in it to not lose the deal.

What I do know is that Sergio figuratively worked and literally showed his (clothed) ass off to get it done.

That was probably the only sale I ever saw Sergio make. While I know there were deals he did worth far more money than that, I’d be hard-pressed to believe that he ever did a deal better than that. I’m not sure how it’s possible to have grace while telling your customer “if you want to fuck me, let’s get it over with right now,” but he somehow did. I don’t like describing the deceased through a commercial transaction, but then again, as I replay parts of this ordeal through my mind, I can’t help but think if this was how he handled himself through that frustrating saga, he probably got through the rest of life pretty damn well.

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Charlie Minato

I am an editor and co-founder of halfwheel.com/Rueda Media, LLC. I previously co-founded and published TheCigarFeed, one of the two predecessors of halfwheel. I have written about the cigar industry for more than a decade, covering everything from product launches to regulation to M&A. In addition, I handle a lot of the behind-the-scenes stuff here at halfwheel. I enjoy playing tennis, watching boxing, falling asleep to the Le Mans 24, wearing sweatshirts year-round and eating gyros. echte liebe.