Your Greatest Gambling Moments

The Game Room
1

“The happiest day of my life was three Sundays ago. I was sitting on my daddy’s knee when the Saints, who were four-and-a-half point favorites, but only up by three, kicked a meaningless field goal at the last second to cover the spread.” – Lisa Simpson
I originally had in mind only sports betting, but other gambling games should also fit nicely into the thread – poker, blackjack, even fantasy football. Whatever.
Probably the single coolest gambling moment for me would be watching the 4th Quarter of Indianapolis @ Tampa Bay, the Monday Night game for Week 5 of the 2003 NFL season. I had some small amount on Indy, probably $50 or $100, who were 4.5 point underdogs. With 5:09 remaining in the game, Tampa scored a touchdown to go up by 21 points. By all rights I should’ve turned off the game in disgust at this point, and I would’ve if I didn’t have money on it, but I was doing a good job of deluding myself into thinking I still had a chance.

And I did! Indy scored three touchdowns in four minutes and 34 seconds, then won in overtime. I’m a really quiet, reserved guy, but even I had to let out an audible yelp when the Colts scored that last touchdown, all but ensuring that I’d win my bet.
Other good moments included a reasonably big tournament win in Atlantic City (item #2 in that post), and my trip to the World Series of Poker – I played three tournaments and failed to cash, but I made up almost all of my tournament losses in the cash games, I got to play in an uncapped, loosey-goosey 5-10 game with over $7K in front of me (most of it the form of $100 bills), and in the tournaments I got to play against *Simpsons *co-creator Sam Simon and former Main Event winner and poker author Tom McEvoy.

2

During my bachelor party I drew 4 Jacks on the gambling boat in New Orleans. That hand pretty much paid for everyone’s rooms at the Royal Sonesta.

Coming back from a vacation we met a buddy at Louisiana Downs that really loved the ponies. He put together a Pick 6 that we bought a piece of. We watched as his picks won the first 5, then 2nd in the 6th. We sent in the ticket anyway in case there was a consolation. The girl came running back yelling “I need a S.S. Card, we won!” Turns out he had made the right pick in the final race, then misremembered. I believe our bet paid somewhere around 40 to 1. 'Nuther trip paid for.

3

Back when it first opened, a local Indian casino paid bonuses for sequential blackjacks. I hit three in a row, collected my $1000, and have never set foot in the place again!

4

For sports betting, I remember being at a Super Bowl party (can’t remember which it was, but it was the Cowboys versus the Bills) when I was something like 12 years old. Everyone was placing bets on the score spread, and my dad gave me a couple of bucks to put down too. I don’t remember the details, it being 15 years ago, but I managed to guess right and got $20 out of it.

For regular gambling, my favorite story when when my family went on a cruise when I was in my mid teens. I was not old enough to gamble, even by the ship’s rules, but I looked old enough (sporting a beard since grade 9 will do that) and my parents didn’t have a problem with me playing the video poker machines. In the space of about 20 minutes, I hit two 4-of-a-kinds. Sadly, my parents appropriated the $200, but that was still pretty awesome, especially when I went to change out the tokens for cash and the girl didn’t even look twice at me. :smiley:

Oddly enough, ever since I got old enough to gamble legally I haven’t gone inside a single casino. I’ve played poker with buddies in my house, but that’s about it.

5

Mine wasn’t so much about the gambling, but the personal moment.

My buddy is a -much- better gambler than me. I’m no slouch, but he’s in the regularly-attends-poker-tourneys kinda field, and I play occasionally with friends. Anyway, one night, years ago, we’re playing at his house, and talking about ‘tells’. I mention that said friend has a very particular one, which I then relate to him. a half-dozen hands later, during a tense bid, he does the tell -exactly- as I said it, and suddenly looks up in horror. Our eyes lock, and the hand is pretty much mine as he curses like a sailor for a minute or two afterwords. :slight_smile:

6

Me:
I was at the horse races and for fun on the last race of the day I boxed three horses in what I thought would be a throw away. The race ended in a photo finish for second place, and I was able to collect on double exactas! It paid for my trip, plus a steak dinner for me and my friends.

My brother was in an Indian casino last week where they have building a ‘bad beat’ pot for a few months. The idea was that if someone lost a ‘bad beat’ in Texas Holdem, then the house would pay out the side pot. A portion would be split between the winner and the loser of the bad-beat, with the other portion being divided up between anyone in the poker room at the time of the bad-beat. My brother was gambling at another table when it happened. I don’t know exactly how much he got, but it was over two thousand dollars.

7

I generally hate wacky-style dealer-calls type of poker, but one time the dealer called tic tac toe, a 3*3 grid you could hit any 3 cards in a row to complete a poker hand when you started with 2. Got pocket aces and the first 2 cards over were aces in a row. Bumped the pot quite a bit, as it was almost impossible for me to lose, as nothing was wild and they’d need a straight flush. So for the next 7 rounds I just toyed with everyone as much as possible in 50 cent poker, mostly betting 50 cents, sometimes a quarter, and maybe even calling once. And no one folded because they were confused by my behavior. I think I got about $20 from that hand, which is pretty good for quarter raise poker.

8

First hand of a $30 buy-in poker tourney I’m first to act and look down at two black Kings. Nice way to start the tourney. Blinds are 25/50 so I raise to 175. I get one caller from middle position (MP) and big blind calls (BB), both solid players.

Flop comes out J96 rainbow. BB checks and I put in 375. MP PUSHES. Hmmmmmm. BB stops for a minute, then CALLS.

WHAT IN THE HELL JUST HAPPENED HERE?!?!? Start with the second best hand in poker, could hardly have asked for a better flop, and now there’s a push and a check-call behind me.

MP MAYBE could have slow played Aces. Maybe someone getting frisky with J9 suited (a favorite hand of many of the regulars). I just about call a couple times since the pot is enormous by that point, but finally I resign myself to the fact that if someone can call an all-in on THAT FLOP, there is no way one pair is good here.

I sigh, muck my cards face up. BB stares at them and says, “That…is a MONSTER LAYDOWN.” Another guys asks why I laid down kings, my friend agrees with me: “Cause they’re no good.”

MP turns over AJ, BB turns over pocket sixes for a flopped set.

In retrospect this shouldn’t have been a hard laydown. But this is a serious leak in my game (more of a hemmorage really). Sometimes it’s almost like I’d rather lose and prove someone had to suck out to beat me than actually make the play I know is needed. If it weren’t for my ego, I’d be pretty damn good at this game.

9

My wife had a great one a couple of years ago. We were in Vegas, playing three-card poker. If you don’t know three-card poker: basically, you place an ante bet and an optional bonus “pair plus” bet that pays bigger if you get certain hands. After you’re dealt your three-card hand, you decide whether you want to play against the dealer or not. If you do, you put down an additional bet equal to your ante. If you beat the dealer, you win on your ante and play bet, and if you get a pair or better, you win a bonus amount, depending on what sort of hand you have. The bonus is paid even if your hand doesn’t beat the dealer’s.

So, I was losing my shirt. I told my wife and the others at the table, “Okay, I’m gonna try to change my luck, I’m throwing a $25 chip on the Pair Plus.” Everyone thought that sounded like fun, and everyone else at the table also put a $25 on the Pair Plus. Of course, that hand was a bust for me. But my wife looked at her cards and got very excited.

Three kings. A super-sweet hand, that pays 30-to-1 bonus odds. So, with a $25 chip on the Pair Plus, that’s a payout of $750 on that single hand, not even counting the win on the ante and play bets. The pit boss was amazed, and happy for us too; hell, it ain’t her money. heh.

My wife won the next hand, too, with a straight flush, the rarest hand you can get. But she’d gone back to $10 chips, so that one “only” paid $400.

10

I won an online poker tournament a few years back for a little over $90k (IIRC at the time it was in the top 5 of all online poker tournaments held to that point in terms of prize pool). I was all but eliminated when we were down to about 20 - IIRC I didn’t even have a complete ante+big blind to post and ended up winning the thing.

It was my greatest moment financially, but nowhere near my greatest moment intellectually. I couldn’t even pick out any specific moment for that either - only that when I’m on the ball I can call out the exact hands of multiple people involved in a hand on a fairly regular basis. Unfortunately this has yet to result in a beautiful woman proclaiming “You sir are a genius! I MUST HAVE YOUR SEED!”, but it does have some financial benefits.

11

Vegas at the Dunes many many years ago.

My first trip to Vegas, my first time in a casino, first time playing craps (except back-alley craps)

Dice come to me at a crowded table, and a rude and obnoxious guy with a stack of $1000 bills (yes $1000 bills) wedges himself to my left. Apparently this guy was well known at the Dunes. He puts one of the bills on the “Don’t Pass”. Pit Boss, boxman, dealers yell out, “Money Plays”. I roll 11. guy loses 1000.

Guy lays down another 2 $1,000 bills on the Don’t pass, I roll a point, roll for awhile, then hit the point.

Rinse, Lather, and Repeat 10-12 times.

the guy keeps laying down $1000 bills on the “Don’t pass” and he keeps losing. I am making my $10 pass bets plus odds and playing the 6 and 8. pressing the bets occasionally.

I end up making about dozen passes before I sevened out, winning about $1500 on my roll and the rude and obnoxious guy drops about $25 to 30 thousand on my roll. After about my 10th pass, he starts gets very loud and obnoxious and rude, and the pit boss asks him to leave.

The table is rocking during the roll, everyone made at least $1000 on my roll. It lasted at over an hour, some of the higher rollers were made $10,000+. One of guys in my group made about $20,000.

Asking dealers later about the guy and they said he owned a couple of the businesses in the Dunes hotel lobby (jewelry?) and he had some old old money stashed away in a safe deposit box.

It was all kind of surreal. A big wad of cash, 1000 dollar bills. There were probably about 50 of them in the wad.

12

December 30, 1999. At the age of 119, Sarah Knaussdies. As a result, I move ahead of my ex-wife to win the office Death Pool.

Ah, such a sweet moment.

13

At a previous company’s poker tournament. I’d never actually played poker before- I’d just played a lot of poker on my smartphone.

Surprisingly, I’d been cleaning up all night, despite my lack of experience. I think it helped that I’d gone into the tournament thinking that I was just going to throw away twenty bucks, and so it didn’t really matter whether I won or lost- I was just there to have fun.

About halfway through the evening, one of my coworkers, Brandon, kinda twigged to my method. During one hand, he started complaining that I was just bluffing- that I was just using my winnings to outspend everyone at the table. Truth to tell, that’s exactly what I was doing- I didn’t have crap on that hand (or many of my previous hands), but I won.

The very next hand, it came down to Brandon and I. I said, “Hey, I’m just bluffing… right?”

He took my bait, and flipped his cards over- two kings. Then I flipped mine over- three aces. Cleaned him out.

I’d never played poker before, but left that night as the winner- an extra $220 for the weekend.

14

I once won a superbowl pool where you bet on the last digit of the two scores and I won $700. I bought a few rounds for everyone in the bar gave the bartender a huge tip and walked home penniless, great frikkin night.

Once I was obviously drunk and sat down at a no-limit hold-em table (this is back when everyone played limit games), bluffed a 2/5 off suit and got a full house on the flop. Everyone figured the flop did nothing for me and I won about $3000 on a 2/5 off suit. 2 guys cursed and got up and left, I never bluffed again that night and got action on all my wining hands.

I was in Amsterdam waiting for a flight out and went to the casino in the airport. The casino employees were making fun of the stupid Americans that threw away their money in a casino airport in Dutch. I was playing slots and hit a 1000 Euro jackpot, the employees all got really pissed off at me until I told them I had another hour to play and then proceeded to win another 1000 Euro on slots and roullette.

15

I was in the casino restroom and a blind woman wandered in. I asked if I could help her and she asked for guidance to the dollar slots. I took her there and she tipped me $7.

16

Shoving a short stack into Phil Hellmuth’s monster pile of chips and getting him to complain that he hates math was a pretty fun moment (he finally called; I doubled up). As was shoving over an Antonio Esfandiari preflop raise with three tables left in one of the WSOP events this summer (I had J9s – he stared me down for forty-five seconds and folded, but I’m pretty sure my hand was good anyway).

17

In a pool for the 1994 NCAA basketball tournament, I picked my future school, the Florida Gators, to reach the Final Four. They were seeded third in their region, but nobody had heard of any of their players or seen any of their games, so nobody gave them much of a chance. They eliminated heavy favorite UConn in OT in the Sweet 16 and then beat another Cinderella, Boston College, in the Elite Eight to reach the Final Four.

18

I won two $1,100+ jackpots at video poker at the Mirage in Vegas, at the same bank of machines, but that wasn’t the standout moment there.

After I won the first one, I was playing a bit more and sitting next to a couple on their honeymoon. The three of us were chatting and after a while the wife asked me, “OK, what do I do here?” She had a A-K-10 of hearts and two junk cards. Throw the two junk cards, I said. She drew Q-J of hearts. Jackpot.

19

My son and I sometimes bet on football games which we watch on TV. The gambling site we use doesn’t shout out at you that your bet was accepted after you placed it so a newcomer wouldn’t know he had bet correctly.

The first time he tried to place a bet my son didn’t know the bet had gone through, so he tried betting again, and again, and again. He tried betting with the points and as a straight win - we had bet on the Titans, an underdog for that game.

We watched the game, the Titans won and that was cool. But not as cool as the next day when I checked our balance.

We’re still in the black a year later.

20

The only gambling I do is the lottery each week. Earlier this year I won a few hundred dollars. Not much compared to what I’ve spent over the years, but it was fun anyway.