Taking a Gamble in 2017: With Skin in the Game, How I Bet, Won Big, and Lost a Little This Year

Posted on: December 17, 2017, 09:00h. 

Last updated on: December 18, 2018, 09:20h.

When people hear that I write about gambling, they usually assume that I hit the tables with gusto. The truth, though, is that I’ve spent enough time around sharp players, casino bosses, and game-designers to know better. Take it from me: randomly splashing money on the felt is a mug’s game.

Tom Brady Super Bowl 2017
Next to Tom Brady and the New England Patriots, no one was more thrilled with their upset over the Atlanta Falcons at Super Bowl 2017 than author Michael Kaplan. The Patriots defeated the Falcons 34-28, and Kaplan made bank, thanks to a sports betting tip. (Image: Kevin C. Cox/Getty)

Unless pressed to play craps with friends or to bet on a sporting event in order to not be the one grumpy bastard who could care less about the outcome, this year, like all other years, I’ve avoided gambling unless I felt that I had an edge.

With that in mind, I’m usually badgering pro sports-betting friends for tips. So, of course, I tapped resources for a Super Bowl pick in January. A trusted pal suggested that I take the Patriots. I did, wagering $400 and being sure that I’d lost until the final minutes of the game.

That’s how I started 2017 with a win on the boards (plus, I aced a prop-bet contest at my Super Bowl party by selecting every low and negative). My wife totally showed me up, though. During a 2016 visit to Vegas, she randomly made a future bet on the Pats going all the way. It snagged her $1,100.

Go, Kaplans!

Weeks later, however, I made $200 basketball bets for my brother and myself. The tip came from the same guy and we lost.

Disappointed, my brother said, “I thought your boy knew what he was doing.”

“He does,” I told him. “But we still have a better than 40 percent chance of losing.”

That’s gambling. Even when you play with an advantage, you can count on losing just under half the time. The reality of calculated risk-taking is enough to derail my dreams of doing it for a living.

When it comes to playing in the pit, blackjack is my game. The good news there is that a guy named Rick Blaine (his book, Blackjack Blueprint, is worth checking out for anyone who wants to learn the craft) taught me how to card count years ago.

I played for a while on a well-financed team, betting as much as two spots of $1,500 per hand. Many casino managers requested that I refrain from playing the game on their properties. So I’m comfortable in doubling down with, say, 10 against Ace when the count hits plus-4 and even hitting with 12 vs 6 when we’re at minus-1.

MIT Blackjack team
Card counting at blackjack, like the notorious MIT team of the 1980s, will make you very unpopular at most casinos, but that didn’t stop our author Michael Kaplan from giving it his all in 2017. Kevin Spacey both starred in and co-produced the 2008 film version of the tale called “21,” and everyone’s had better luck than he has this year. (Image: memolition.com)

It also means that I know others who card count. The most fun you can have in a casino is sitting down with friends who are counting seriously, for big money, and throwing out a green chip every time you see them ratcheting up their bets. My single-monikered buddy Jo and a guy she was partnered with allowed me to piggyback. I won maybe $600 on that session this past spring.

As her partner sourly stated after we finished, “It’s easy to win when you only bet with the best of it.”

This past summer, I wound up playing with them, out of a common bankroll and with more seriousness of purpose. One weekend was profitable, to the tune of like $800 each. Not all the money in the world, but it was a helluva lot of fun, except for the time that one of us, who shall go nameless here, got booted out of a casino.

On a second trip, we employed a slightly more adventurous playing technique, did pretty well, and never got popped. But then, as departing flight times neared, we hit an ugly losing streak while card counting at an off-Strip casino. The timing couldn’t have been worse, and the trip ended up as a wash.

As the year wound down, I had a final jaunt to Vegas. It was all about reporting stories, quaffing cocktails, and being a gourmand, with the most memorable meal being a beefy feast with an insanely tasty duck and goat-cheese terrine at newly opened Bavette’s in the reconfiguring Monte Carlo on the Strip.

But I did manage to slip in a few small-stakes runs at the tables, betting units of just $5 and $10, with a max bet of $100.  That brought some eyebrow-raising from a pit boss at my favorite dump downtown, who gave me one of those “I’m watching you” glares, while asking, “You spread from $10 to $100? Interesting.”

I played sessions of just a shoe or two and managed to win a little more than $500 over the weekend.

Lesson learned for 2018: it’s good to get a little lucky, but, man, you sure wish you had more money on the table when those moments of good fortune strike.

Michael Kaplan is a New York-based journalist. He has written about gambling for The New York Times Magazine, Wired, Playboy, Thrillist, British GQ, and Esquire.com. Kaplan has authored or co-authored four books, including “Aces and Kings: Inside Stories and Million-Dollar Strategies from Poker’s Greatest Players.”