What's your most satisfying gambling experience? -- some great stories

Other Sep 22, 2020

Earlier today on Facebook, I posted a simple question to my readers:

What's your most satisfying gambling experience?

Here's the way I phrased the discussion, which triggered nearly 100 replies, so far – and it's only been a few hours since the discussion began.  The stories continue to roll in.

Today's Question:  

What was your most satisfying gambling win or accomplishment?  It's a simple question.  But I'm not looking for the biggest monetary win.

Try this.  Dig a little deeper and think about the gambling-related accomplishment that brought the biggest smile to your face.  Think of satisfaction in the broadest possible terms.

Here's my answer.  This is my most satisfying gambling accomplishment.  It happened more than 30 years ago, and it still brings a smile to my face:

In the winter of 1987, I joined a group of friends on a ski trip to Lake Tahoe.  We planned on staying and playing for six nights, skiing at Heavenly.  The all-inclusive package included airfare, ground transportation, and a hotel room at Del Webb's High Sierra.  So, everything was prepaid except for meals, drinking, skiing, gambling, tipping, and entertainment (in other words, I still needed a significant bankroll).

A few days before departure, I got hit with every conceivable financial beat -- sports betting losses, my car broke down, maxed out credit cards, etc. etc.  I was wiped out financially and had a six-day non-refundable trip to South Lake Tahoe. Somehow, I scraped together something like $178.35.  Borrowed a few dollars.  Sold some record albums.  I dug out spare change from the sofa cushions.  

We flew into Reno and arrived at the High Sierra and suddenly a massive snowstorm hit.  One of the worst in a decade, they said.  Snow was so heavy and winds were so high, they closed down the ski resorts.  So, now -- I was stuck in a casino, with what amounted to emergency cash.  Had I been able to ski 5 full days, I might have stretched out the money.  Now, all there was to was was gamble and drink.  It was 0 degrees outside.

The reason why this gambling story was so satisfying was because -- somehow, someway, by some miracle -- I stretched out that $180 and it lasted six full days.  A $10 bet on a basketball game.  A $25 win at blackjack.  I nickel and dimed my way the entire trip, never missed a meal, enjoyed free drinks, went to the nightclub with my friends each night (we were couples, mostly), and even skied 3 days instead of 5 when Heavenly finally reopened.  I needed to win twenty bucks and sure enough somehow I'd win a $20 bet somewhere.  When I needed to buy my lift ticket which cost like $45 for 3 days and I only had like 27 and change left I'd take one shot at the dice table and roll the natural.  Pure luck.  Bingo.  I never had any significant win, but when I was down to my last $40, somehow I ran it back up to $85 on some gambling thing, and therefore I could wake up the next morning for a new day.

I recall the flight was scheduled to leave early Monday morning and by late Sunday night I was down to my last few bucks.  I think was 2 am when I lost my last hand of blackjack and was for all intents and purposes -- completely BROKE.

Such an experience might normally be a time to panic or be sad.  But when I stepped into the elevator to ride up to the room, I recall feeling a smile come over my face that I could not contain.  I'd squeezed every last value out of that $180 over six days, never missed a beat, had the time of my life, and felt as though I'd hit life's lottery.

Strange to say losing money is "satisfying" or "an accomplishment," but it was very much both.  Since that trip 33 years ago, I've won and lost an incalculable number of wagers.  But for six days in the winter of 1987, a series of losses added up to a huge win, and a wonderful memory.

Now, for the responses.  Here are some great stories posted by readers:


I was playing low limit BJ at the Barbary Coast just killing time before I met someone. I was being lazy and just playing basic strategy. I guess I was up a little bit. All of a sudden the pit boss comes over and says something to the dealer. The next thing I know, the dealer is shuffling up every time I raise my bet. Now the Barbary Coast had a reputation as being a real burn joint but I couldn't believe they were sweating nickel action. So now I took this as a challenge. I started counting cards and just flat bet when the deck was good and raised my bet when the count went negative knowing the dealer would shuffle up. I got lucky and won a couple hundred dollars and quit. Now that was fun!

GREG RAYMER (2004 World Series of Poker Champion, who won $5 million that year)

Similar here. Was at the long closed Pioneer casino downtown (home of Vegas Vic, the waving cowboy). I was counting, single deck game, and they shuffled as soon as I raised my bet. Like you, I started flat betting 4 units, and would double up when the count was negative. Then reduce to 4 while the dealer shuffled. I thought they would catch on and kick me out, but they let me do it for an hour, then I quit.


Gambling generally doesn't hold much for me.My first time in Vegas, I was just flying through but I had a 5 hour layover so I left the airport and went via taxi to the strip. I got some quarters and sat down at a penny slot machine - I was going to gamble just to say I did.I put my first dollar in and pulled the lever. 600 credits - a whole $6! I was ecstatic. I played about 10 minutes on those credits and was busted. As I stood to walk away, I took one last look at the machine. The machine I thought was a penny, was actually a dollar. I had been up $600 and pissed it away in minutes.20 years later, I still don't mind it as a "beat." I had a lot of fun for $1, and its a fun story. The $600 was never "mine" so I didn't lose it...I just wasn't smart enough to take it while it was offered. I won the story though.


The Mayweather-McGregor fight. It was easily the most money I ever had at risk for a single sporting event. I didn’t buy the fight, but I could watch it online, and I was sweating the first few rounds. I wanted to believe Mayweather was toying with him, but McGregor was having more success than I had envisioned, and I was really getting nervous.Just as the 5th round ended, my 3 1/2 year old daughter asked me to read her a bedtime story. I cannot say no to her, plus I figured that was the universe telling me to stop sweating the fight. Then of course, she picked the longest book she could find! I’m reading it to her at top speed, but it’s still a solid fifteen minutes before I’m done. Just as I’m getting to the last page, I finally can’t help it. I sneak a peek at my phone, just as Mayweather scores the late TKO, which is the exact outcome I predicted and allowed me a perfect sweep. After I read the last line to her, even though it wasn’t part of the book, I practically shouted, “And they all lived happily ever after, THE END!” We both slept well that night.


I suppose I could say winning a bracelet, but honestly, as much as I’d tortured myself trying to win one, it was much more of a relief than satisfaction. This one sticks out more:  In 1976 I left my hometown, Troy, NY, in an old car, with perhaps $800 and whatever I could pack in the car and drove west. I always loved to gamble and, unless I came across something amazing, my first destination was Vegas. I got there with about $500.For whatever reason, I thought I had a way to beat craps. I stayed in a cheap old motel called the Domino, north of the Sahara. I played craps at the Sahara every day and naturally found I couldn’t win, leaving me with $60, few options and a lot of trepidation.  I had an old friend who had moved to Riverside, Ca a few years earlier and had invited me to stay with him if I chose. I decided it was time to get out of town, but, as broke as I was, felt the pull of the gambling devil. I swerved into the Aladdin parking lot with the $60 I had left, promising to just play $20. I tied into a hand and ran it up to $400. I remember thinking, hey maybe I was just unlucky before, and was at a crossroads; stay or go. Thankfully, I came to my senses, got in my car and drove to Ca, where I bounced around for four wonderful and memorable years.My buddy and his cousin were living in a rented house and had a room for me. Eventually we had a stream of friends from Troy coming out, soon having 10 people in the house, none of whom had any money. It was the best time of my life.I made my way back to Vegas in 1980 for good, but I still think about the choices I made and how that lucky win kickstarted my adult life.


Getting out of an Estonian casino alive after counting their BJ game. I had max bets across on a super juicy shoe. The host of the poker tournament I was there to play pulled me off the table and said “The goods news is, they aren’t going to kill you....as long as you quit blackjack for the rest of the trip”. A 26 year old kid in Tallinn for a week with 50k kroon in his pocket made for a very memorable experience.


When I lived in New Orleans I often used to go to the Fairgrounds and watch the horses run around and bet a little money. After awhile I got really into it and started going deep into the numbers and trying to handicap the races. Since I was never betting much money, I was always looking for undervalued long shots. In the 2012 Louisiana Derby there was a horse named Hero of Order I liked at a morning line of 50:1, when I thought he should have been something like a 10:1. I knew it was unlikely he would actually win, but it was a big discrepancy. That day I had to work, so I couldn't attend the race, but I had a friend make a few bets for me, including a dollar on Hero of Order to win. I also told him (and his family that were going to the race) to do the same. Sure enough, Hero of Order won, the biggest longshot to ever win the LA Derby, and by race time his odds had gone all the way up to 109:1. The next day my friend handed me a cool $110.40. He hadn't taken my advice, but several members of his family had. My only regret was that I wish I'd trusted my intuition and handicapping a little better, and just bet $10.


Mine was when I was propping at a casino and hit the jackpot. The first part was the hand itself. I lost with four kings to a king high straight flush (both hands made on the torn). But I only lost 6 big bets. Capped turn and called a river raise. I just knew what he had in my bones. Called his raise on the river, and said “I think we’ve got it, and we did!” Almost 60k.But the best part of the story was that I had swapped jackpot action with a really good buddy who propped on graveyard. So when he came in I got to tell him he made almost 20k whole he was sleeping. It was really cool.


Years ago and recently divorced I stopped in Vegas on the tail end of a business trip. Lost about $3K but had a big smile when I realized I didn’t have to explain it to anybody!


I used to Train and Drive Standardbreds..in 95' 96' I had a Very Fast 2yr that would Over Accelerate into a break if not handled properly. After earning over 200K at 2, we sold him for $440K... They had trouble getting him back to the Races @3 and after 4 starts he earned $11K..Then he got hurt and they couldn't sell him. When the price went Way Down to $12K we bought him and. I fixed him and earned another $150K besides cashing tickets many times. Most satisfying Gamble Ever !!!


This could be the world's largest collection of losing horseracing tickets.....

Hollis Thompson Barnhart

This is my most satisfying. I only won $1200 tho. About 40 years ago, when National Airlines was in business, I was driving on Paradise Rd and saw their advertisement. “Fly to Dallas, New Orleans and Miami”.....I knew that was my three team parlay. I bet $200 and BAM!! All three were easy covers.

Contributions are also coming in from Twitter:

And finally....

Craig Moskowitz

It’s a 3 way tie. When I was still living in New York in the late 80s I would take trips to Atlantic City to count cards at blackjack. I was able to beat the 8 deck shoe games somehow. I really enjoyed my trips there. Very cool to go out to the beautiful boardwalk to clear your head after gambling in smoke filled casinos. I mean you walked out of Trump Plaza and the Atlantic Ocean was right there. Salt water taffy! I’m pretty sure I was running real good during this period. So on this one trip I must have showed up under-bankrolled, with maybe only $1500. So I proceed to lose and lose some more and was starting to run out of money. I found myself in the middle of a shoe with a very high count. I was playing two hands with a $70 bet on each. I was dealt a 9 and a 2 on each hand. The dealer was showing a 6!!! I wanted to double down on each but didn’t have enough chips on the table. So I start reaching into my wallet. And I start pulling out 20’s, 10’s and 5’s to cover the bet. I remember the snide female dealer saying “you can double down for less, sir”. Finally I get together the money for the double down. I got an ace on one hand and a useless baby card on the other hand. But then the dealer busted! That bust was an immediate $560 turnaround. And then for the rest of my trip I went on a heater and ran it up to 10 grand! I used to stay at one of those cheap Indian owned motels right out of town where you can smell the curry. I remember putting the whole $10,000+ on the saggy bed, having never before seen so much money. In typical stupid gambler fashion, I blew about a grand on a new sports jacket and pants at the casino men’s shop.Fast forward a few years and I had moved to Las Vegas. For some reason I always would win at Caesar’s Palace. So even though that place had terrible shoe penetration, I still played a lot there because there was so much big money action that I would never get “heat” there. My puny $70 bets was nothing compared to the next table where often thousands or at least hundreds was being bet on each hand. I also got completely greedy and was not doing sit down play, instead standing behind the tables and counting, jumping in when the count got high ( I knew my blackjack days were numbered as I was starting to get heat all over town. So I was milking BJ for all it was worth before the inevitable transition to poker). One day out of nowhere several CP security guards approached me and asked me to go with them. Oh, shit! They took me to a back room, asked for my ID and then told me that I was free to leave but that I was barred from any CP property for life, and would be arrested for trespassing if I ever returned. Even though this was bad news for my gambling career, I still felt it was so cool that me, a Jewish kid from Queens had drawn the attention of the mighty Caesar!!!And finally, in 2013 I won the seniors $400 buy-in NL holdem event at the Venetian for a cool $9500 payday. The poker room put my picture on Facebook and I got a trophy. I never won any kind of trophy before, so that was so nice.BTW, to this day, whenever I'm dealt a Montana Banana at poker, I flash back to that hand in AC.

There's much more where these came from (75 stories, and counting!).  Join the discussion on FACEBOOK.