The 10 Biggest Gambling Lessons I’ve Learned in the Last 20 Years

My first experience gambling was at the Sands Hotel and Casino in Las Vegas in 1996. I’d never gambled before, and I’d never been to Las Vegas before—or any other casino city.

Before that, the most gambling I’d done had been at small, penny-ante neighborhood poker games (dealer’s choice, of course).

The first gambling game I ever played was roulette, and I was amazed at how quickly I won even money on a bet at the roulette table. To hear my dad tell it, all those gambling games are rigged against you.

Since I walked away from the roulette table a winner my first time out, I thought maybe there was something to this gambling business that my dad didn’t know.

It turns out, I was right. My dad was, too, in a sense.

Since then, I’ve learned A LOT of lessons about gambling. These are the 10 biggest gambling lessons I’ve learned in the last 2 decades:

A break even game is one in which you’d break even over the long run if you kept playing it. In other words, the odds are “fair.”

Here’s an example of a break-even game:

If you bet on a coin toss 100,000 times in a row, you’d probably lose about as money as you’d win. The chances of getting your guess right when tossing a coin are 50/50.

You can change that break-even game into a game where one side has an edge over the other with one quick change to the rules.

Instead of winning the amount you wagered, you’re required to bet $1.10 to win $1 when you get it right.

Over time, the other person would win money—that’s called having a mathematical edge. That specific example is pretty close to how the business of sports betting works.

You win 50% of the time, but you lose slightly more money than that on the 50% of the bets you don’t win.

There are 38 numbers on a roulette wheel, and 18 of them are red, while 18 of them are black. The other 2 numbers (the 0 and the 00) are green.

So you have 20 ways to lose versus 18 ways to win.

It’s easy to see how in the long run the casino makes money this way.

Most of the time, when you’re placing a bet, you’re placing that bet at a mathematical disadvantage.

Some gamblers specialize in only betting when they have a mathematical advantage.

Those gamblers are called advantage gamblers, and some of them are good enough at it that they can make a living from their gambling activities.

I didn’t realize just how important skill was to the game of poker until I’d studied it some.

I’d always heard that skill was a big part of it, but before I knew anything, I assumed that the skills involved had to do with bluffing and deciding when the other players were bluffing.

There’s a lot more to poker than that.

The basics have to do with estimating your probability of winning and comparing that with the odds the pot is offering you if you do win.

Here’s a simple example:

If you estimate that you have a 1 in 4 probability of winning the next pot (3 to 1 odds), and there is $600 in the pot, if the bet is under $200, it makes sense to call it.

The pot is offering you 3 to 1 odds in that case, making this a break-even bet.
If the bet is $150, you’re getting 4 to 1 odds, which is even better. At $100, the payoff odds come in at 6 to 1.

You can find games in the casino with a higher house edge than the slot machines, but not many of them. Even in Las Vegas, which is home to some of the loosest slot machine games in the world, the house edge for most slot games is over 6%.

The house edge is the average amount that the casino expects you to lose every time you place a bet on a game.

It’s based on the probability of winning versus the payout for winning—as I discussed above in the section on flipping coins and betting on the roulette wheel.

Most of the table games in the casino have a house edge of well under 5%. In the case of games like baccarat, blackjack, and craps, the house edge is well under 2%.

This means 2 things—you’re more likely to win in the short term (usually), and you’ll lose less money on average in the long run.

And that 6% number?
It’s optimistic, and it’s a wild guess.

You have no way of knowing what the house edge is on a specific slot machine. The house edge can always be calculated for a table game, because the odds of winning and the payout odds are known.

In fact, you can have 2 identical slot machines sitting side by side, and the computer program that generates the results can have 2 different settings.

One of those games might have a house edge of 6%, while the other might have a house edge of 12%.

I’m not a fan of slot machines, although I do play them occasionally.

To be fair, though, I never much liked them. I just didn’t see the point to playing a game where I didn’t get to make any meaningful decisions.

I’m philosophical that way.

No game in the casino has a lower house edge than blackjack, but to attain that low house edge, you must play with perfect basic strategy.

Luckily, perfect basic strategy is easy to find on the internet or even in the casino gift shop. And it doesn’t take a rocket surgeon to memorize it.

It’s a simple enough game. You play versus the dealer, and you each start with a 2-card hand.

The cards have point values, and you add those values to get the score for your hand. A total of 22 or higher is a bust, or an automatic loser. If you get a total closer to 21 than the dealer without busting, you win even money.

Some of the time you’ll get a 2-card hand worth 21 points. That’s called a “natural” or a “blackjack.” In that case, you get paid off at 3 to 2 instead of even money.

The card values are easy to remember, too. The numbered cards are worth their numbers—the 2 of diamonds is worth 2 points, the 3 of spades is worth 3 points, etc. The face cards are worth 10 points each, and an ace is worth 1 or 11 points, whichever is better.

Really, all you’re doing is tracking the ratio of high cards to low cards left in the deck. You do this by adding 1 or subtracting 1 depending on whether a low card or a high card has been dealt.

When the count is positive, meaning that a lot of high cards are left in the deck, you raise the size of you bet.

High cards, for purposes of this discussion, are cards worth 10 or 11 points. If there are more of those cards in the deck than usual, you’re more likely to get a 2-hand total of 21 and get that 3 to 2 payoff.

Of course, casinos frown on card counting, but it’s still worth pursuing if you enjoy a challenge on multiple levels like this.

I’ve written at great length in previous columns about why I dislike the lottery, but I never get tired of ranting about it. Here are my big problems with the lottery:

• 1. The odds are lousy.
• 2. The state government shouldn’t be operating a casino.
• 3. The money doesn’t really go to education the way the lottery proponents say.

You know, I mentioned that I don’t much approve of slot machines, too.

But I also pointed out that not only do I sometimes play slot machines, I occasionally even enjoy it.

The same is true for the lottery.

But I try to take a reasonable approach to playing the lottery.

I read that the scratch-off tickets offer the highest payback percentage. I haven’t talked about that concept before now, but you can think of payback percentage as being the other side of the house edge coin.

For example, if a game has a 5.26% house edge, it also has a 94.74% payback percentage.
Most casino games have a payback percentage of 88% or higher, although that’s not true of all of them. (Ahem, I’m talking about you, keno…)

The payback percentage for most lottery games—especially the big drawings like Mega Millions and Powerball—hovers around 50% most of the time.

If the jackpot grows high enough, the payback percentage can go up, but it becomes largely irrelevant when it’s almost impossible to win that top jackpot.

That’s like playing a lousy slot machine game, but you don’t have a machine to deal with.

The highest denomination scratch cards I’ve seen were $20 each, but I’ve also seen $10 tickets and $5 tickets. I bought a couple of $20 tickets this month, and I also bought a $10 ticket this month. I won nothing.

With a $50 investment and a 65% payback percentage, I should have won $32.50, but this is as good example of how in the short run, you won’t see the mathematical expectation very often.

Not long ago I played poker at a buddy of mine’s house—it was a low limit home game. We were playing $1/$2 no limit Texas holdem, but we each only bought in for $40.

And there were only 4 or 5 of us playing.

At one point, I won a pot without a showdown because everyone folded in the face of my raise.

The guy hosting the game, a good friend of mine, reached over and flipped my cards over.
If you fold, you don’t get to see what my cards were.

That’s the deal. It’s one of the rudest things you can do in a poker game, in fact.

I called him out on it, and he told me that since it was his house, they were his rules.
I think he was a little drunk, but still.

Another time, I won a pot against a guy wearing a Frito-Lay jacket when we were playing at a casino in Oklahoma. I had a reasonable hand, too—AQ preflop.

The guy was the favorite right up until the river, but I drew out on him. I don’t even remember what he was holding or how the flop and turn happened.

All I remember is that he got so mad about the bad beat that he almost came across the table at me. I think he flipped me off, too.

You’re more likely to find jerks at home poker games, in my experience.

Not long ago, I started dating this wonderful woman. I was just crazy about her, and she seemed to be crazy about me, too.

After we’d been dating for a couple months, a friend of mine invited me to celebrate her boyfriend’s 50th birthday with them in Las Vegas.

And I invited the new girlfriend. We’d been dating 2 months.

Now, I only fly first-class, because I’m not only overweight, I’m also really tall. The airline tickets were $875 each. (She’s tall, too, by the way—6’1”.) We were going to fly on Delta.

Anyway, a week before we were about to leave on our trip, she had lunch with me and explained that she’d met someone else. She cried and cried, but she still broke up with me.

I didn’t think it was that big a deal, because I’d just met a redhead who was a former Dallas Cowboys cheerleader. She dug me, and she really wanted to go to Vegas in the place of the former girlfriend.

I called Expedia, and it turns out that I’m not allowed to change the names on the tickets. I can’t get a refund, either. I do have credit toward a future flight, and I can use that anytime between now and August.

That’s for the best, though, because I had to drive the redhead to check her into the mental hospital a couple days later.

I have bad luck with women, I guess, although, I’m still friends with both ladies.
I just wish I’d know the first one longer before planning a trip to Vegas with her.

I might have prevented some disappointment on my part by making sure it was going to be a long-term deal.

Then again, women and men break up all the time for various reasons and in various time frames. There’s no guarantee that the woman you’re in love with won’t break up with you, even if you have a trip to Vegas planned.

I know people who are obsessed with their gambling activities to the exclusion of everything else. A lot of times these people are poker players or sports bettors.

I even know some people who I’d consider slot machine zombies or addicts.
Don’t get me wrong.

I like to gamble, too. I’ve even spent too much time gambling at a casino on an occasion or two.

But as I’ve gotten older, I’ve learned that there are some life experiences that are far more important and fulfilling than winning a big pot at the poker table. I have kids now, and they’re wonderful.

I love spending time with them, whether we’re watching movies or TV programs or visiting bookstores or whatever.

I also have a host of friends who I do things with—long conversations smoking cigars, drinking coffee, or just hanging out. And I’ve been blessed with some of the most beautiful and interesting women in the world to date.

Gambling can sometimes be a nice addition to these things, but it’s like the frosting on the cake. Who wants frosting without cake?

I took an ethics class in college, but we didn’t discuss the concept of sin. We did discuss different ways to decide whether something was moral or not.

In a sense, gambling could be considered a sin. After all, this is money you could be using for useful purposes like feeding the hungry or clothing the poor.

When you think about it that way, sure, gambling is a sin—and it’s immoral to boot.

But take that argument to its obvious eventual conclusion and you won’t even be able to buy a movie ticket without thinking that it’s immoral.

I don’t think it puts my soul in danger, or yours.

I’m not a preacher, though, or a theologian, so don’t quote me on this.

10- Having Some Money in Action Makes Betting on Sports a LOT More Interesting
I grew up with dad watching football on television.

In fact, I grew up in a small town in northeast Texas, so football is what it’s all about around here. I never enjoyed it much.

In fact, I might not really ever have enjoyed watching any kind of sports if I hadn’t learned that you could bet on these things.

Once I was able to put $100 down on a game, I found a way to enjoy watching sports—live or on television.

I don’t care if I’m betting $20 with a buddy or $2000 with a sportsbook, I just enjoy having some money riding on the game I’m watching.

I’ve learned a lot about gambling over the last couple of decades, and I’m sure I have some more lessons to learn over the next couple of decades.

These are the gambling lessons I’ve learned.

What gambling lessons have you learned throughout your life?