Funniest, craziest, wildest gambling stories: Post them here

[Steve-O]

Based on his Filthy Limper appearance I think Templar is going to run away with this one, but I have a few gems up my sleeve as well, so here is the first one (Note: this was an older article I wrote a few years ago):

The $4,000 tip - I'm not a fan of casino games (the odds are always with the house), but I do play them now and then, for fun, or to pass some time.

After an all-nighter at the poker tables, I was waiting for a friend (who will remain nameless) by playing a little 3-card poker. If you've ever been to a casino at 8am on a Tuesday you know that I would bring the average age of the table I was at down by about 40 years!

All things considered, I was having a very good time, and was in no rush to leave. I was on a very good winning streak, when my friend came up behind me wearing that look only a gambler knows; the look of a man who had lost a lot of money. He took one look at my stack of chips and asked if he could play behind me, since there were no empty seats.

The dealer dutifully changed his $300 into chips and slid them toward me. My friend was explaining his bad luck, and how he was down about $2,000, when I turned to ask him, "how much do you want to bet?" His response was, "bet $100". However, before I could turn around to place his bet he asked me for $1 to tip the waitress. So I dug into my pocket looking for a $1 bill, handed it to him, and turned back to the table to place his bet.

This is where the plot thickens, as they say. The dealer had already begun dealing the cards with only my $10 bet placed, so I turned back and said, I'll get you in next hand", his response was, "no problem." To which I added, "it would suck if I had a straight flush."

For those of you unfamiliar with 3-card poker, you are paid based on the strength of your hand: a straight flush pays 40 to 1, 3 of a kind pays 30 to 1, and so on.

You probably can guess what my hand was at this point....... 6spades, 8 spades, last card......... 7 spades!

What made the situation all the more surreal was the clapping, and congratulations from the collection of grandmas at the table. They were so happy for me, and my $400 win! The look on my friends face said it all; a strange combination of disbelief, disgust, and utter shock. He never said a word, he simply took the $300 in chips he had cashed in and went to a different table. This was by far the worst $400 I have ever won in my life.

He showed up a few minutes later, down an additional $500, and definetly ready to go.

It's true that timing is everything; I guess it also helps if you keep $1 in your pocket to tip the waitress, so you don't have to ask your friend for it and miss a bet!

[Steve-O]

Here is story #2 (also from an old article, but in the forum I'll add in a few extra details):

Jackpot! - This time we find ourselves in the slots area; where a friend (thankfully a different friend than the one from the 3-card poker fiasco) is idling away the time playing the quarter slots.

When we finally found him he was down to $1.00, and decided to play $.50 each spin. On the first spin he hits the jackpot... THE ACTUAL JACKPOT! He starts flipping out and a flurry of "oh my gods" and "I can't believe its" come out of his mouth.

We are all screaming and going crazy; when he stops and says, "why isn't the light going off?"

At this point the little old lady [she was black and spoke in that sarastic "mmmm hmmmmm" way], she had to be 80, on the machine beside him decides to see what all the yelling is about: She slightly lowers her glasses, and leans toward him, to get a good look at his machine.

She raises and then lowers her little granny glasses as she looks at the machine, looks at my friend, looks at the machine, and back to my friend one more time, looking him dead in the eye she says, "you stupid mother fucka!, you gotta play max bet, you didn't win shit fool!"

As we all stood there she walked away mumbling, "always play max bet... always play max bet... Stupid mother fucka!"

It turns out that by playing two quarters instead of three (remember there were four in the machine) my friend cost himself over $30,000 since this was a progressive jackpot machine. Even worse is the amount of times he has to recount this story since anyone who is aware of it always brings it up when the subject turns to gambling; you can see the pain in his eyes every time he tells it, even years after the fact. But, it's a very funny story, so he got that out of it!