11 Points

How I Started Winning at Gambling When I Finally Bet Against Myself
written by Sam Greenspan

I'm not good at gambling.

I like the action, but whether it's blackjack, poker, craps, the sports book, slot machines, roulette, fantasy football, three-card monte, pick a hand, guess how many gumballs are in the jar or anything else -- I pretty much always lose. I've always been responsible enough not to lose too much money, but virtually every Vegas trip I've been on has ended with most, if not all, of my gambling budget disappearing into the "let's build a new hotel tower" fund. Not quite the worthiest of causes, although some of the extra towers I've helped pay for are pretty nice.

I am so bad at gambling that it defies logic. Yes, the casino always has the advantage and should win more often than not, but at some point the law of large numbers would say I'd piece together a win. Never really happened, though; I don't have any memories of any particularly transformative wins.

But in May of 2013, that all changed. I am now a tremendous gambler. And I owe it all to one thing.

I started betting against myself.

I started playing craps about six years ago. I had some strong beginner's luck but eventually settled in to my traditional pattern of losses followed by losses followed by a few more losses.

If you don't understand craps, that's ok. The only thing here that's important is everyone gets a turn rolling the dice, and a shooter keeps going until they hit a 7 ("crap out") and everyone loses.

But if they can roll for a while without hitting a killer 7, that's when craps is at its high energy, high payoff peak. There's nothing quite like a hot shooter. When someone's rolling and not hitting a 7, people throw down more bets all over the table, start printing money with all of them, and the volume gets loud and raucous.

Unfortunately, every single shooter will eventually hit a 7, because you roll indefinitely until you hit that 7. When you hit it, everyone loses everything on the table. Sometimes they will've won a lot of money in the lead up, sometimes not. Either way, every turn ends with everyone on the table losing.

What if it didn't have to be?

In May of 2013, I had my bachelor party in New Orleans. My friend Jared and I were at its Harrah's casino and he suggested we try an experiment. Instead of playing craps the way most people play it, let's play the opposite.

In craps, there's a lesser-known option to bet against the table. Every bet is inverted. You're rooting for the shooter to roll the 7 -- because when he does, you get paid. Unfortunately, everyone else who's playing the traditional way loses, which is why this style of so craps is unpopular.

Every book, article and website will recommend you avoid this style, which I'll call "don't pass" craps -- even though its mathematical odds are better than playing the traditional way. The first negative cited by every source is the magnanimous, social side of craps; playing the "don't pass" doesn't just eliminate you from the camaraderie, it actually makes you an enemy of the table. You are, quite literally, rooting for everyone to lose so you can win.

And there are other downsides too, beyond the whole antisocial aspect.

One, the bets pay terribly. As the house, and with the inevitability of victory assured, your bets pay the same as sports book bets on a big favorite. Think, say, Indiana University versus Indiana University of Pennsylvania in basketball. A $100 bet that the shooter will roll a 7 before he rolls a 4 will only win $50. A $100 bet on the (riskier) proposition that the shooter will roll a 7 before he rolls a 6 will only win $83. Every bet has the equivalent of a negative money line. It would be like going to a horse racing track and betting the favorite to place in every race. You may win a lot of those bets, but only for small amounts each time.

Two, because of those low odds payouts, the money trickles in slowly and the losses sting hard. Let's say in the above scenario the shooter does roll a 4 before a 7. You lost the $100, and now you'll have to have the next two shooters roll 7s before 4s just to make up your losses. That means you've got to have a good bankroll, especially if you have to weather the storm of a hot shooter. You also need the risk tolerance of having a lot of money exposed on the table (although you really need that to win playing craps the normal way too.)

And three, because no one starts their craps life in the "don't pass" world, every time you do encounter a hot shooter and lose a bunch of anti bets, you're immediately filled with a ton of doubt about whether you should've gone over to the dark side. That feels even worse when you're the shooter and you actually have a good roll. (Fortunately for me, that's not an issue. Again, I'm a bad gambler. I don't have good rolls. I roll just well enough that everyone puts money on the table, then gets burned big time when I crap out.)

I always lose to the house. So the "don't pass" method appealed strongly to me -- because, essentially, you become the house. Since every turn ends with a 7, you're guaranteed to win eventually every single time -- if you have the bankroll to last through a successful shooter.

Unlike traditional craps, where you lose everything on a 7, there's no roll of the dice in the "don't pass" world where you lose all of your bets. But there IS a roll where you win all of your bets -- and it's the 7, which happens to have the best odds of coming up of any number. The bets don't pay as well, but they can add up fast.

And the antisocial thing is hard -- especially for someone like me, with debilitating empathy -- but it helps to play this style with a friend, not to celebrate too much, and to cheerfully explain the strategy to all of the people around you when they ask why you keep winning. (Very few people know the nuances of "don't pass" craps, but many, many people inquire about it literally every time I'm playing it.)

But it's worth it for me, since "don't pass" fits me well. I couldn't win the traditional way. It's the only option in the casino to win money by being traditionally unlucky. It's shorting stocks, but with a market that trends downward overall, not upward. There's no need to make gut-wrenching decisions on when to increment my bet (which kills me in blackjack), no need to try to control my involuntarily emotive face (which kills me in poker), no need to pretend my sports fandom translates into being able to make quality predictions (which kills me in sports betting). I win by losing, and boy, am I good at losing.

Since I started playing "don't pass" craps, I've only had two times walking away from the table empty handed. (Versus traditional craps, where I might've only had one or two times walking away from the table not empty handed.)

Jared, who introduced me to "don't pass" craps, had his bachelor party last summer. I returned the favor on playing "don't pass" craps with him, like he did for me.

We both paid for our trips.

There's something here on a macro level that originally bothered me about the idea of "winning by losing." This is some pretty casual nihilism. I was raised in the "you go, girl" '80s and '90s; not quite as pronounced as that sentiment has become today, but still a part of me. If in my everyday life I believe my grand purpose and ultimate solution to is to bet on myself, can directly defying that in gambling truly just remain compartmentalized? Or will it seep into other parts of my life? Will I start "don't passing" my career, my family life, my other goals?

And the conclusion I reached is... absolutely not. If anything, I'd take it as a sign of personal evolution -- but I don't think I need to take it as a sign at all. I'm not betting against my skill, I just identified an unexpected niche skill -- being a gambling pariah -- and bet on that. It's a paradox I'm proud to embrace.

This post was originally published on Tuesday, July 19, 2016 at 11:00:00 AM under the category Games.

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