Winners & Losers: Gambling Dad

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With a staff job at a tabloid newspaper in New York City, I recently found myself on the Diddy beat. That is, covering the wild scandals currently surrounding Sean “Diddy” Combs.

One story of mine concerned a guy who brought his six-year-old kid to a party at Diddy’s Hamptons mansion back in 1999. The son remembers pot smoke and naked women.

Retrospectively, it probably was not the smartest thing for his father to do.

sean diddy combs new york city
Image: John Mathew Smith/Wikimedia Commons

The story got a bunch of traction and left me wondering about possibly inappropriate things I exposed my kids to when they were little. I did not have to think for very long.

They’re both adults now, but, back when my two daughters were 7 and 4, I played on a high-stakes card counting team.

As long as the casinos thought I was a regular, money-spewing blackjack player, gambling without an edge, they treated me very well.

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Comped suites, fancy meals, limos at the airport, they all came with the package.

Sometimes I traveled alone. Sometimes I brought my family. Because, well, why not? It was a lot of fun.

They’d hang out with my wife at fancy hotel pools in Las Vegas and Atlantic City and beyond while I chased down games and tried not to get chased out.

atlantic city - gambling dad
Image: Shinya Suzuki/Flickr

We aimed to shield them from too much of the casino life, no one wants a five-year-old to know casino etiquette before they can do multiplication, but it was hard to keep the kids from noticing scantily clad cocktail waitresses on the edges of casino gaming floors.

I got a kick out of them mimicking the voice that announced floors on the Borgata elevator, in AC. It had a very specific way of saying Cah-see-no.

I can’t say I loved it when we flew to Paradise Island for a comped trip and one of my kids wondered if we would have a suite as she casually stepped into a waiting limo.

Maybe I should have told her that this was not normal, but it would have been a lot to explain.

Plus, when the Atlantis put on a sweet fireworks display – it was July 4th weekend – and we had a good view from our balcony, well, that tilted whatever mixed feelings I had.

Nevertheless, one time, when we checked into a normal hotel on a regular family vacation and one of the kids asked where the casino is, I had a moment of pause.

Then there was the weekend when I played a casino in Connecticut. For highly desirable players, the joint had a special hospitality suite with gratis food and drink. My kids went crazy for the excellent chicken fingers.

The plan was for me to make my blackjack strategy pay for one final session on Sunday morning. Then we would chow down on the chicken fingers and head back to New York City.

But I got backed off, my comp was revoked and let’s just say that I was no longer considered a highly desirable player.

“Uhm,” I told my eager children, “the chicken fingers are shut down today.” Not a complete lie, though they were shut down specifically for us.

“We’re going to a really great pizza place instead.”

mystic pizza - gambling dad
Image: daveynin/Flickr

We stopped at the nearby Mystic Pizza, which inspired a movie of the same name and serves superior pies. The pizza was tasty but the chicken fingers were better.

Weirdly, my older daughter recently rekindled a friendship with a girl she knew while growing up. I was pals with her dad. He and I met up once in Las Vegas, back in the day, and he watched me crush a blackjack game at Caesars Palace.

When my daughter happened to come across the father, while hanging out with her old friend, the first thing he said was that he saw me win a bundle at a Vegas blackjack table.

My daughter was surprised, not incredibly cognizant of the stakes and a little impressed that I managed to do it. That made me happy on all counts.

Plus, it taught me something: Where kids are concerned, casinos a better than Diddy’s parties.

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Michael Kaplan
Gambling Author and Journalist
Michael Kaplan
Gambling Author and Journalist

Michael Kaplan is a journalist based in New York City joined Techopedia in November 2023. He is the author of five books ("The Advantage Players" comes out in 2024) and has worked for publications that include Wired, GQ and the New York Post. He has written extensively on technology, gambling and business — with a particular interest in spots where all three intersect. His article on Kelly "Baccarat Machine" Sun and Phil Ivey is in development as a feature film.