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The pleasures of small luxuries aside, one is not likely to encounter the ultra-wealthy at any San Diego County cigar smoke shop/lounge. Unless you’re downtown, at Seaport Village, or maybe Del Mar or La Jolla — it’s just a bunch of local guys — disposable incomes aside — attempting in some inchoate fashion to reconstruct a few of the social connections severed by the new “connectivities” of our times.

Part of the sociability of the cigar scene derives from the sense that cigars, as they’re marketed, are an indulgence that — while available to all — are meant to appeal to folks who appreciate the “finer things in life.” There seems to be some truth behind this construct; while not in any real sense an “elite” group, San Diego’s cigar smokers would appear to be discernibly different from their distant, desultory cousins, the cigarette fiends. One man’s take was emblematic.

Dave G. was first “turned on” (he hesitated to use the term “hooked”) a few years back during the mid-’90s boom. His first cigar was a Cuban Montecristo #4, in cigar-speak, a corona (six inches long with a 46–ring gauge diameter) supplied by a fellow financial planner at a backyard gathering. “I’d never smoked tobacco before,” he told me. He’d always regarded cigarettes as the province of white trash, the uneducated and unsophisticated, the corpulent

Wal-Mart shoppers who didn’t give a shit about their health. He mused, “You know, when I bought my first box of cigars, I thought, ‘Here I am, a guy with a couple of advanced degrees, from a family of physicians, no less; I’d been warned about the dangers of tobacco for decades. Could I really enjoy these things? Yes, I thought, hell yes!’ ” Nevertheless, his wife and kids still give him grief, which is why — when he tires of the stale solitude of his garage — he heads for a cigar lounge or cigar dinner.

Even if your wife doesn’t condemn cigars — doesn’t require that you undergo a full-body skin transplant before you step inside the bedroom and tolerates breath that smells like the lobby of a downtown flophouse — there are more than enough politicians (including some who actually smoke them) who’d like to tax cigars out of existence. If Charlie Hennegan has a nemesis, and his supremely mild manner would suggest few enemies, it’s the tax man.

Charlie’s first cigar, a very mild Macanudo, did not portend a future as a tobacconist, much less a pro-cigar activist. “I was in college at Loyola of Baltimore on a double date, and the four of us went down to Georgetown in Washington, D.C., to party. I wanted to show my date that I was a bon vivant, I guess — a “man of the world” — so I lit up a cigar and proceeded to get very sick.” But after learning how to smoke without inhaling, he discovered the joys of the leaf and began the smoky trail that would take him from “green” novice to standout retailer and champion of cigar smokers.

I first met Charlie Hennegan in 1997 at a book-signing event at the Borders bookstore in Carmel Mountain; he was there in conjunction with Dale Scott, who’d penned a quirky little volume, How to Select and Enjoy Premium Cigars. By then, he’d owned Liberty (where he started as a customer) for a dozen years. Not long after that, as I became a Liberty “regular” (well, not as regular as some), I realized that Hennegan and Scott had something in common beyond cigar “aficionado” status — a live-and-let-live libertarianism that not only recognizes but celebrates the sort of visceral pleasure one derives from good food, drink, and smoke. But Charlie does more than extol the virtues of a well-made cigar; he’s actually a political activist, of sorts. Beyond his informal role as a cigar “goodwill ambassador,” he’s an advocate for an industry that he feels has been unfairly singled out for criticism and abused by outrageous taxation.

Soft-spoken, low-key, and downright courtly, Charlie doesn’t seem like a guy who’d carry a grudge; but if he has one, it might be directed at Rob Reiner and his fellow Hollywood types who’ve (successfully) urged California to impose, in recent years, some of America’s most onerous tobacco taxes. As vice president of CART, the California Association of Retail Tobacconists — a 350-store trade group he helped found a decade ago — Charlie has long battled sanctimonious politicos. “Over the years,” he tells me, “I’ve expended a lot of energy fighting [California ballot initiatives] Propositions 10 and 86.”

Few things in life make Charlie fume (and he’s hard to vex) like the blowhard bureaucrat who’d like nothing better than to tax cigars right out of existence — or at least make them available only to their well-heeled benefactors. Charlie also bridles at the refusal of politicians and others who, atop the high horse of “public health,” willfully fail to distinguish between cigars and cigarettes. In a peculiar way, Liberty Tobacco — with its humorous cartoons and articles posted on walls, counters, and cabinets — reminds me of an “activist” bookstore or record shop with a patriotic (but libertarian) slant, all of it filtered through a pleasant haze of burning leaves.

Second on the “most wanted” list of any tobacconist is the online seller, typified by giants like Cigar International and Thompson Cigar. Huge volume, the lack of state sales tax, efficient shipping, and most of all, avoidance of California’s massive tobacco tax have enabled Internet smoke shops to cut into the locals’ territory. But unlike some small businesses — San Diego’s nearly extinct local record stores come to mind — “brick and mortar” smoke shops survive, even thrive. I asked Charlie why his customers prefer (at least some of the time) to battle traffic to get to his shop, where, by his own admission, he can’t match the online sellers’ prices on brands they both sell.

Having spent more than a few hours browsing the Liberty humidor myself, I already knew the answer, which might be described as a “filler” of good products, held together with a “binder” of cigar experts, and covered with a “wrapper” of warmth and bonhomie.

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hudel19 Oct. 1, 2008 @ 10 a.m.

What a great article, it is nice for the cigar smoking community to get some informative and positive press. However, it would be a great disservice to San Diego tourists and the local cigar aficionado not to mention Excalibur Cigar Lounge & Wine Bar - Miramar. I subscribe to their email newsletter and decided to attend a recent Rocky Patel event. When I got there I was blown away by the newly constructed walk-in humidor and expanded lounge. I saw some pictures of their new humidor beforehand on their website www.excaliburcigarclub.com but the images do not do the place any justice. You have to see it in person. Anyway, I agree with this article that there are some nice cigar shops scattered all around San Diego, but if you have never been, I highly recommend Excalibur, Miramar. They are doing good things over there.


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