What's your best train wreck gambling story?

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ed8

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Jun 7, 2009
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Damn, one of my employees is up shit creek, no paddle, no boat, raging rapids ahead with concrete blocks on! Dude started playing 3 months ago, 25 and 50 dollar bets, hit a cold spell and started chasing. Well, he got down 9k and to pay his man he got a title loan on his wifes car. Fast forward to today, he comes in and not only is he out 9k for the car, but is down another 7500 trying to get that 9k back!!! I sat him down, told him to stop now and get another job to get it back but knowing him he is just gonna go deeper. So what's your best train wreck gambling story?
 

Oh boy!
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Mar 21, 2004
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Went 14-0 for College Football Playoffs buying a tout's picks and won $1600+. A friend of mine was in it with me. I still remember taking $100 bills and throwing them up in the air and letting them fall down on me.

Fast forward a couple months. I lost $3200 on College Basketball with the same tout's picks. I ended up paying my local $100 per month and quit gambling. He would let me skip making a payment a couple times here and there so it took me about 2 years to pay him off.

I didn't gamble for another 17 years.
 

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we went to the casino 2 weeks ago. a colleague of mine, fucking degenerate, thinks he can beat the house everytime he goes there. he had some great runs, especially bj and roulette, where he made a couple of dimes in a week. i told him many times, forget about it, if you win its plain luck. get your money, and get the fuck out. the longer you stay, the more money the big boss will suck out of your pockets.

i was sitting playing BJ just for fun, was on a roll, won a couple of chips, ordered another drink, while of a sudden i hear a man screaming at the roulette-table. thought he lost his fucking mind, but it was something else. my colleague put a first hundy on his lucky 21 and he hit it. over 3.5 large in his pocket, he's happy as hell.

we've ordered something to eat at the restaurant, nice bottle of wine, a little steak. talking about what we're going to do next. i wanted to hit the bars/clubs, he wanted to play some craps, bj, just for fun he said. i said to get the fuck out of the casino, get some booze, go to a club etc. he wanted to stay, i couldnt leave him there, so we stayed for a couple of more hands of bj.

took a piss, than my phone rang, i went to the smoking section for a cig, talked with my girl, usual bullshit. approx. 20 mins later, when i came back to the bj and roulette room, this guy dissapeared. i asked the croupier of the table he won at, if he saw my colleague, but he nodded like a fucking retard.

went up to the other room, and there he was. sitting at the table with his hands across his face like a fucking baby. almost crying. he was playing bj, $100 a hand. 'dealer has 21' was the grand finale of his last $100 bet.

ok sounds nothing special, cos he only blew the casions 3k, right? wrong! in the time i was smoking, the fucker lost the 3k, then took a small loan from his brother, to get the 3k he lost back. he said it was another 3 dimes, i think its a lot more. i dont know how the fuck he did it, and his brother isnt any smarter than him giving out the loan. i think its in the genes.

if you gamble with somebody elses money you really have a problem.

ps i won $100 that night, after being up almost 6 bills
 

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