Vegas Trip: Celebrating 50 in Sin City

Cigar Aficionado's gambling guru, Michael Kaplan, recently turned 50. He and two childhood friends of a similar age decided to celebrate in style, with a guy's trip to Las Vegas. Their golfing, smoking, drinking and eating escapades are a model for any cigar aficionado traveling to Sin City. Here's how it happened.

Everybody loves a milestone. It reminds you of how far you've come, provides a chance for introspection and offers an opportunity to look forward. On the most self-serving level, it's usually cause for celebration as well: We made it! We're still alive! Look at how great we are!

Having turned 50 this year, I saw such a milestone right in front of me—this was a birthday worth signifying. But how? There was talk of throwing a party at our house in Brooklyn. My wife suggested bringing in a chef to make a kick-ass dinner, augmented by appropriate wines and Cubans on the back deck. But then I had a conversation with two friends of mine, Steve Weil and Glen Landesman.

Pals since second grade, we grew up together in the suburban New Jersey town of Elmwood Park. Steve hit the magic number last May. Glen and I got there earlier this year. For all of us, the birthday felt like a big deal. Over plates of porterhouse at Peter Luger, we chatted about how to properly commemorate our achievement. Consensus came before the dessert: a blowout weekend in Las Vegas would be in order.

The idea was to celebrate good lives, a future that glistens long-term, and plenty of success thus far: Glen is a physician, Steve owns a popular retail operation, and I've written three books and cover gambling for Cigar Aficionado. Clearly we've all been fortunate, and we are proud and thankful for our accomplishments.

We were returning to familiar ground. The trip lined up almost perfectly with a Vegas jaunt that we took 30 years ago. The three of us were still in college, it was my first time boarding an airplane, and we stayed at a dive on the northern end of the Strip, not far from the motel where Stu Ungar (then the wunderkind of Vegas) would breathe his last.

The author, Michael Kaplan.

Back in those days we had no connections, no money, and, really, no clue. My most pristine recollection of Vegas, circa 1979, is walking up the big, landscaped frontage of Caesars Palace, being greeted by a man dressed like a Roman gladiator, and feeling too blown away by the glitz of it all to process very much. The trip ended with Steve and Glen flying back to New York without me—I made a last-minute detour to Los Angeles to hang out with a punk-rock girl I had met earlier in the journey.

This incident happened three decades ago, but the story still gets a lot of mileage, as Glen and Steve love recounting the expression on Mr. Landesman's face when he picked them up at Newark Airport and discovered that I had remained out West. Alternately, his look is described as one of bemusement and disgust. But, being a father, I now know what the look really was: The expression of relief that it was not his kid running around Sunset Strip with a Joan Jett doppelgänger.

Whatever the case, we had no doubt that this trip would be elevated way beyond the first one. We vowed to do Vegas right, spend three, exhausting days hitting the town hard and living it up in celebratory fashion.

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