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Dan Ippolito

As Casino City's associate editor, Dan produces and edits all of our weekly newsletters, and he writes about the gaming industry for our websites and the GPWA Times Magazine. Dan graduated from Marist College in 2017 with a degree in Communications and a concentration in Sports.

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Top 10 mistakes I have made when gambling

28 Apr 2025

By Dan Ippolito
Nobody’s perfect, right? Well, that phrase stays true when it comes to gamblers.

Despite learning more strategies and casino etiquette over the years, it is easy to slip up every once and awhile. So here, we take a look at 10 mistakes and unlucky moments that I have made and experienced throughout my gambling history, most occurring early on.

10. Forgetting to use my player’s card
When walking into a casino, many may choose to sign up for the loyalty program of the property in order to gain points from playing and make progress toward rewards and other benefits.

I have done this at a few different casinos but early on in my gambling days, I had at least a few times where it slipped my mind to put my player’s card into a video poker machine or slot during a session and missed out on a decent chunk of points and potential free play.

When playing, always try to remember to put your card into the machine. At the tables, it is a little easier to remember because the pit boss often will ask if you have a card so they can run it for you.

9. Standing on 16s
One of my first times ever stepping foot into a casino was at Foxwoods Resort Casino in Connecticut. The game that always interested me was blackjack and I immediately made my way over to a low-minimum table to get my feet wet.

Now, I was familiar with the objective and a decent amount of correct plays, but I had not learned basic strategy to the fullest which left a few holes in my decision making.

On a few occasions, I stood on 16 against a dealer’s nine or face card. While it paid off sometimes, it isn’t the correct play according to basic strategy and it ended up in losses more than not.

While nobody was rude to how I played the hands, after a few occasions, I did ask the dealer if that is the right move and they told me it is usually a hit and from then on I made the right move.

The sevens just kept coming.

The sevens just kept coming.

8. The forbidden number
While I began playing blackjack, after a while, I did start to expand the number of casino games I would play.

Craps didn’t come into my arsenal for a couple of years because of the intimidation of how complicated the game looks and the number of bets you can make.

When I finally mustered up the courage to hit a craps table, it was definitely a memory but for the wrong reason. I mainly stuck to playing the pass line and I bought a couple of numbers here and there, but then the dice finally made its way to me.

My first throw had a crazy bounce and one of the dice flew off the table, which was a little embarrassing. Then my next roll I set the point and everyone else at the table started firing chips on the table to bet. My next roll was an immediate seven . . . awesome.

It took another 15-20 minutes or so for my turn to come around again and I set the point and then, boom, another seven right after. This would happen two more times in a row. I felt like I could have thrown the dice off the ceiling of the casino and it still would’ve landed a seven. Talk about beginner’s BAD luck!

7. Getting attached to side bets
Going back to my first time at the casino, later that day, my father and I found another blackjack table in the afternoon.

The side bet was Match the Dealer and I played it very hand and was really cleaning up on the side bet. However, this probably hurt me more than helped me because I was under the assumption that side bets pay out often.

Because of this, my next couple of casino trips I was hammering the side bets and got cleaned out because they just simply were not hitting. I got lucky catching a little hot streak on Match the Dealer, but really understood that isn’t often the case.

6. Not searching for the best payouts
It is unfortunate, but the fact of the matter is that many casinos are changing from 3:2 blackjack payouts to 6:5.

So during one of my first Las Vegas trips, I just sat down at a blackjack table at the first casino I stepped in and played for an hour or so without realizing there were better paying tables a casino or two over on.

Do your research or keep your eyes out for the best possible payout options to maximize your take.

5. Touching chips too early
Another popular game that I have come to enjoy is roulette. I tend to enjoy playing the numbers on the inside but I have also dabbled with the outside such as even or odd, black or red.

Once at a roulette table, I was placing bets on about 10 numbers per roll and I hit a number which I got paid out for, but I made the mistake of going to add another chip to the already existing bet on the number that just hit.

I wasn’t aware that I couldn’t add or touch chips until everyone had been paid out from that roll and all the losing chips are cleared and I was quickly told that by the dealer.

Know basic strategy.

Know basic strategy.

4. Not splitting nines
Heading back over to the blackjack table, this is one that was an easy learn after making the mistake once.

I had a pair of nines against the dealer’s eight. My first thought was I have a good hand and if the dealer has a 10 under, I don’t lose.

I should have been thinking, I can turn this 18 into two hands of 19 and double my winnings. Unfortunately, I stood and the table made their individual decisions and it was time for the dealer to play their hand. A quick flip of the under card showed an ace and the dealer had 19 which beat my 18.

This stems from me not knowing basic strategy at the time but was just another reason that led me to really learning it. Basic strategy calls for a player to split their pair of nines when a dealer is showing a two through six, and an eight or a nine. You shouldn’t split against a seven because you must assume the dealer is going to have 17 and the pair of nines would beat that hand.

Another zero spin.

Another zero spin.

3. Pulling my bet down
In roulette, you can see what numbers have come up recently on the screen near the wheel which can help you determine which numbers are hot and which are very cold.

Well, during one of my roulette sessions, I was playing the numbers inside and I was also splitting 0 and 00. All I needed was one number to hit in order to get to slightly positive on the day and 0 was lucky enough to hit and I took my chips and pulled my bet down and was set to walk away.

While this is still a smart thing to leave when you are ahead, this is more of an unlucky occurrence.

I stayed to see the next roll and it was 0 again. I had to stay to see one more spin and a total gut punch came when it hit for a third time in a row. I could’ve really cleaned up, but that’s just gambling. A lot of what ifs.

2. Chasing losses
During my first trip to Las Vegas, my second day on my trip I went to The Venetian Las Vegas and sat down at a blackjack table with a friend.

We had some ups and downs through the session but toward the end of the fourth shoe, things started to really turn poorly and we seemed to not be able to win a single hand in the blink of an eye.

Frustration started to set in and we tried to chase losses and get even with one hand and went all in with our stacks. MISTAKE. A dealer blackjack was the nail in our coffins and taught us a nice lesson.

1. Going to the ATM
I am a strong advocate for this rule now, despite having succumbed to the other side of it when I was younger.

Do not go back to the ATM to take out more money to gamble. Go into the casino with the amount of money you are willing to lose.

I mentioned earlier about a few times side bets really drained my bankroll and I wasn’t expecting how quickly that your money can fly away when betting side wagers.

My session was much shorter than I was hoping for so I went to the ATM and took out another few hundred. While I didn’t lose much of it, that is besides the point. Going over your planned budget should always be avoided. Plus, you should also want to stay away from the hefty ATM withdrawal fees that many machines located inside casinos have. Some in Las Vegas can get you for $10.
 
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