4 Gambling Stories You Can Learn From

Caesar's Palace Outside Statue and Closeup of Roulette Table Mixed Image

I’ve been gambling for close to 40 years, and I’ve made just about every mistake you can imagine. While the stories on this page aren’t my favorites, the truth is that you can learn quite a bit by reading about some of my failures.

Here are four stories that highlight big mistakes that I’ve made so you can avoid them.

1 – You Can’t Lose

Early in my gambling career I fell into the same trap that many gamblers fall into. I was playing roulette at a low limit table making minimum bets. I was making even money bets and was slowly losing my stack like you expect if you understand how the house edge works.

Another guy playing at the same table was doubling his bets after losses and looked like his stack was growing while mine was shrinking. I started talking to him and eventually he explained his system. It turns out was the Martingale system, but at the time I didn’t know anything about it.

After he explained the system to me he said you can’t lose. And I have to admit that it sounded so good that I couldn’t imagine how I could lose. So I started using the system and won several playing sessions in a row.

Sadly, the odds eventually caught up with me and I lost everything I’d won in the previous sessions and more. At the time I couldn’t understand how a close to 50/50 wager could go against me so many times in a row.

The worst thing about this experience is I have a degree in mathematics. But I never ran the numbers before my big loss. The truth is the math behind roulette and every other gambling game makes the Martingale system a long term losing system.

Most gamblers have to learn this the hard way, and it usually costs them a lot of money. They see the system at work or read about it and buy into the “I can’t lose” belief. They never take the time to run the numbers.

Don’t make the same mistake that I made. This way you can avoid losing too much money learning what I finally figured out.

2 – The Sure Thing

Before I get into this story, I want to be completely honest with you. I’ve made more money than I’ve lost using what I’m about to tell you about. But it isn’t enough to justify the huge risks required to try it. I still make a few of these bets every year, but it’s not one of my normal betting strategies.

Every sports season there are some games where a powerful team plays against a weak team. The powerful team is so much better than the weak team that sometimes the only bet available is a spread bet. But sometimes the sportsbooks offer a moneyline on these games.

Here are a few examples of matchups with huge favorites:

  • The Alabama NCAA football team against a weak non-conference opponent early in the season.
  • The Duke or Kentucky basketball team against the worst team in their conference in any given year.

You might see a moneyline of -5,000 or some other outrageous number. In case you don’t know how moneyline wagers work, in this example you have to risk $5,000 to win $100. To win the bet, all the heavy favorite needs to do is win the game.

While the odds are heavily in your favor when you bet the moneyline on a huge favorite, the problem is that there is no such thing as a sure thing. I’m sure you can’t imagine how North East Tennessee State University or some other small college can knock off Alabama; the truth is that every year a few heavy underdogs win.

I’ve also seen this type of thing at the horse and dog track, and it’s even worse there. The way the odds and pay outs are designed when you bet on horses or dogs is the higher percentage of the total betting pool that’s bet on the favorite, the lower the odds and lower the pay outs go.

A Busy Roulette Table

Many bettors see a heavy favorite and think that the horse or dog is a sure thing, so they bet on them. The problem is that when you bet on a heavy favorite and win, you secure a very small return on your investment.

When the heavy betting favorite loses, you usually lose more than you win when your bet wins. And the problem with heavy favorites at the horse and dog track is that just because the majority of bettors are betting on one horse or dog doesn’t mean the horse or dog really has a better chance to win.

The rule you should follow 100% of the time is any time you start thinking that a bet is a sure thing or hear someone say that a bet is a sure thing; you should not make the bet. In the long run you’re going to save money by avoiding all sure thing wagers.

3 – Speed Is Everything

Over the years I’ve bet on horses and dogs quite a bit. I know that some gamblers are able to make a profit on these races, and I enjoy watching the races. But the truth is that it’s hard to be a profitable track bettor.

Most winning track bettors have a system of some sort that they use to help them make winning bets. Knowing this, I’ve tried my hand at designing several race track systems over the years. I’ve even come up with a couple that win as much as they lose. But I’ve never designed one that is a long term winner.

The closest I’ve some is using a heavy amount of speed to rank horses or dogs.

It makes sense that the fastest horse or dog wins, but the problem is there are too many variables when you’re basing your wagers on past results.

Some of the issues include the condition of the track during the past races, how much rest the horse or dog has between races, pole position, and the jockey in horse racing.

I’ve seen horse racing systems that use total race speed, opening speed, closing speed, and just about any other speed metric you can think of. I spent six months developing and back testing a speed based system for harness racing at one track based on the horses and jockeys and once I put it into use it barely broke even.

The truth is if you can design a system that breaks even you might be able to keep tweaking it to make it a winner. But I scrapped the project because I didn’t want to sink another six or 12 months into it for the small gains that might or might not come.

The moral of this story is that speed has a great deal to do with picking winning horses and dogs, but it’s only one of many variables that you need to consider. If you want to be a winning race bettor start with speed, and be ready to work for months or years to develop a consistent system.

4 – Taking Stupid Chances

I’ve been playing poker for close to 40 years, but it took me at least 2 years to figure out how to be a winning poker player. I’d like to be able to say that once I started winning that everything has been great, but I still make mistakes from time to time.

Fortunately, I’ve been able to learn from most of my mistakes over the years, but a few of them were quite costly and stick with me years later. The hand I’m getting ready to tell you about happened soon after things started coming together and I started winning more than I lost.

Looking back at this hand it’s easy to see how stupid my play was, but at the time I wasn’t as good as I thought I was. In the long run this hand was profitable, because I instantly learned my lesson and the experience has saved me a great deal of money over the years. The experience has saved me far more than it cost me to learn my lesson.

I was on the button in a real money Texas holdem game. I don’t remember the exact stakes, but I had around $500 in my stack, had been playing for quite a few hours, and was up several hundred dollars on the day.

One player to my right limped into the pot and I limped with an ace with a face card. This was the first mistake and one that I don’t make today. This is the perfect raise or fold situation, and raising is the best option.

Closeup of a Man With His Casino Chips

The small blind completed his bet and the big blind checked. The flop was all low uncoordinated cards and it was checked around to me. I bet and the small blind called. The other two folded at this point. The turn was another blank, the small blind checked, and I fired a larger bet into the pot.

This wasn’t the worst play I’d made, because sometimes you have to fire the second barrel to win a pot when your opponent is weak. The important point is that I put myself in this situation because of how bad I played the hand before the flop.

This still wasn’t the optimum play at this point because I didn’t have a made hand and I could see the river for free. But I bet and it cost me. The bad news is I was so stubborn that I didn’t stop the bleeding at this point.

The small blind went in the tank and put on a great acting job. He even went so far as to check to see how much more cash he had in his pocket to buy back in if he lost the hand. He finally called and checked to me again on the river.

The river didn’t improve my hand and once again, the smart play was to check and minimize the damage from my terrible play. Guess what I did. I fired another big bet into the pot. At this point the small blind raised all in, and it was such a small amount that I called.

He had a monster hand, and I lost all of my profit from the day and more. I was sitting there with ace high and a stupid look on my face. The only good thing was I called him on the end so I could fold my terrible hand without showing anyone.

In one hand I destroyed all of my profit because I took stupid chances. Everyone makes mistakes, but I compounded my mistakes by digging the hole deeper. The best idea is to not take stupid risks in the first place, but once you take one, stop as soon as possible. Don’t compound the problem by backing up a stupid mistake with others.


One of the best ways to improve your gambling skills is to learn from your mistakes. It’s even better, and less costly, to learn how to avoid mistakes by learning from the mistakes of others.

Don’t fall into the trap of you can’t lose or sure things bets. Avoid taking stupid chances and falling for the speed trap when handicapping horse and dog races. If you learn from these four stories your bankroll will thank you.