6 True Stories from a Real-Life, Middle-Aged Gambler

It might not be readily apparent, but I take my responsibilities as a gambling blogger seriously. After all, if something is worth doing, it’s worth doing right.

And last week, I read a blog post about how to create better content, and the advice was simple enough:

Write about your own personal experience as much as possible.

That inspired my latest post, which is a collection of anecdotes from my own life.

Since I’m 50 years old these days, I probably qualify as a middle-aged gambler – even though I don’t think I qualify for AARP yet.

Here are 6 true stories from my life along with the lessons I learned from each situation:

1- Shuffleboard Tournaments on Thursday

Not long ago, I wrote a post about real money gambling on stuff that you might not think of as gambling immediately.

In other words, it was about betting on billiards at the bar, or darts, or event a game of Monopoly with your kid sister.

The best example of this from my own life is the weekly shuffleboard tournament I participated in at my local bar for 10 years.

The bar is still there on Forest Lane, but they haven’t done shuffleboard tournaments there in years. I stopped drinking 6 years ago, myself, so that’s probably for the best.

But for 10 years, I participated in a weekly shuffleboard tournament there. The entry fee was $10, and you got to draw your partner randomly.

I’m NOT a good shuffleboard player, although over the course of a decade, I did improve.

To be honest, often, I was too drunk to play at my best.

The owner of the bar would sometimes throw an extra $50 into the prize pool, which worked like this:

The team that won the tournament got to split the money, and the team that came in 2nd place got to play in the following week’s tournament for free.

I think I was a poor enough shuffleboard player to beat the odds, though.

In 10 years, which amounts to 500+ tournaments, I only won once. (I did place 2nd several times.)

I sometimes got paired with the best shuffleboard player in the bar, but that usually wasn’t enough to put us over the top.

In fact, one of the 3 or 4 best players in the bar got really mad at me for making a mistake and losing a tournament for us.

Lesson learned.

The moral of this story is to take it seriously when someone else’s money is involved.

2- All Night Underground Poker Games in Dallas

I also used to play in several of the underground poker rooms in the Dallas area in the 2000s. I don’t know how many of them are still there – I know that at least one of the poker rooms I enjoyed visiting got raided by the SWAT team.

These games were a lot of fun, and I met a lot of interesting characters.

The best night I ever had was one where I played from 8pm to 8am.

I played a tightly-focused, disciplined game where I folded A LOT.

I wasn’t catching cards, either, so I didn’t get to make any moves until 5am or 6am, but, at that point, I started getting hit by the deck.

It was a $2/$5 pot limit game, and I bought in for $200 or $300 and treaded water most of the night.

But I went home with $1000 in winnings and slept soundly all day that day.

Even my wife, who was skeptical about my poker hobby, was impressed.

The moral of this story is to stick with your game plan even when the cards are running cold.

3- Counting Cards in Kansas City

Speaking of my wife (now my ex-wife), we took a trip to Kansas City early in our marriage, and, while we were there, we gambled at Harrahs.

I’d read a book on card counting and was proficient enough to keep up with the count and bet accordingly.

I’d also had quite a few drinks that night. I called it camouflage, but the truth is this:

I was drunk.

I had a betting spread of $10 to $100, and I thought I was doing a great job of raising and lowering my bets according to the count.

In was up $200 or so after an hour, but then I realized something:

The dealer was shuffling after every hand.

They knew what I was up to, but they didn’t care enough to ban me from the blackjack game or run me out of the casino.

I was up $200 out of sheer, dumb luck – not because I was counting cards.

The moral of this story is that drinking and gambling don’t mix.

4- Winning My First Online Texas Holdem Tournament

I participated in a home poker game in the late 1990s for years, but we never played Texas holdem. We played a lot of silly games like 5-card draw and 7-card stud, but holdem just wasn’t on the menu.

In the early 2000s, though, when I got involved in the online gambling industry for the first time, I learned to play Texas holdem so I could participate in a friendly game with some other gambling writers.

After a while, I decided to try my hand at a poker tournament, so I found one with a $10 buy-in at Party Poker – which, at the time, still served the United States market.

I was so new to Texas holdem that I’d read a chapter in a book about getting an edge while gambling and made myself a strategy sheet on a piece of paper. The strategy was mostly about ring game play, but it worked in the tournament.

I wound up placing 6th out of several hundred players, and the prize money was $5000.

A $5000 return on a $10 investment isn’t bad, and, after that, I was determined to learn more about how to play winning poker.

I’m not a great player, but I break even as often as not these days.

The moral of this story is that in some situations, even a little bit of a game plan can give you enough edge to have a chance of winning a big pot.

5- Big Don, Poker Player and Doctor Tilt, the Chiropractor

When I was playing in the underground cardrooms in Dallas, my favorite experiences had to do with getting to know the characters at the poker table.

One of my favorite opponents was a big 300-pound macho man named Big Don. He once called my raise after I’d folded pre-flop 45 times in a row, saying, “You’ve folded preflop 45 times in a row. I just HAVE to see what you think is worth raising with.”

He didn’t look like the kind of guy who made his living from nail salons, but that’s what he did – he owned 9 nail salons throughout the city.

Another of my favorite local characters was a chiropractor we called “Doctor Tilt.” We called him that because he was always getting mad and donking off his chips.

He was there wearing scrubs every night. We always assumed that he worked at a hospital and came to play cards after getting off work, but it turns out that he owned his own chiropractor practice.

He dressed for work so that he could go straight from the cardroom to his office in the morning without changing clothes.

After work, he’d go home and sleep until it was time to get to the cardroom.

The moral of these stories is easy enough – enjoy the colorful characters you meet while gambling.

6- English Only at the Poker Table

I was playing poker at the MGM Grand in Las Vegas the day before a business meeting I had scheduled with Minneapolis Jim Meehan, the poker player. I was pitching him on the idea of being his webmaster.

The dealer at the table was a surly, bald Russian – I don’t remember his name.

But at one point during the game, I went all-in and said, “Carpe diem.”

The Russian dealer told me, “English only at the table, sir.”

I sheepishly explained to everyone at the table that “carpe diem” was Latin for “seize the day.”

He told me, “ I KNOW what it means, sir – but when you say something in a foreign language at the table, you might be signaling someone.”

I asked him, “Couldn’t I be signaling someone if I just said, ‘Seize the day?’”

The Russian didn’t like that.

When I told Jim the story the next day, he told me that he would have chewed out the dealer and asked the cardroom manager to fire the guy.

I don’t think it was that big a deal, but I did learn this moral:

English only at the poker table.


Those are 6 true stories from my life as a gambler. They’re amusing anecdotes, but they all really happened, and I tried to learn a lesson from each of them.

What lessons have you learned from your gambling experiences?

Let me know in the comments.

Michael Stevens

Michael Stevens has been researching and writing topics involving the gambling industry for well over a decade now and is considered an expert on all things casino and sports betting. Michael has been writing for GamblingSites.org since early 2016.

Recent Posts

2021 NFC South Preview: Can Tom Brady Lead the Bucs to a Division Title?

The NFC South is going to look a little different in 2021. For the first time since 2005, Drew Brees…

August 2, 2021

2021 NFC East Betting Preview: Can Dallas Bounce Back to Win the East?

In 2020, the NFC East was considered the worst division in football. The Washington Football Team ended up taking the…

August 2, 2021

Outright Betting on Champions League 2021/22

We won’t beat around the bushes today! We have a ton of information we need to serve, most of which…

August 2, 2021

2021 AFC West Betting Preview: Can Anyone Dethrone the KC Chiefs?

Last year, the Kansas City Chiefs once again dominated the AFC West division. Led by their explosive offense, the Chiefs…

August 1, 2021

2021 NFC West Betting Preview: Who Wins Toughest Division in the NFL?

The NFC West is shaping up to be the toughest division in football for the upcoming 2021 season. Over the…

August 1, 2021

Can You Bet on Preseason Football for the 2021 NFL Season?

We are almost to the end of July, which means football season is only a few sleeps away. While bettors…

July 31, 2021