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Thread: worst bet ever

  1. #1
    Funny story--at least I think it was funny. Last Thursday before the Bears- Packers game to open the season, I'm at the race track and some guy is carrying on all full of himself talking about the Bears and the Super Bowl and how great they are. I'm a big lifetime Bears fan but I don't share his view this year and think Trubisky is pretty bad. So he's going on and on and finally I say they'll be lucky to outscore the Cubs.

    Obviously, my statement is ridiculous hyperbole as a football team is always going to outscore a baseball team. So anyway he says I'll bet you anything you want that the Bears will outscore them. The smart thing to do would be to walk away, but I would rather blow $50 than walk away. So I tell him I'll bet $50 but I want odds. He says I'll give you $100-1 on as much as you want. I tell him he doesn't even have $5,000 if I were to win, so let's just make it 10-1.

    That day the Cubs get 10, the Bears get 3. So I win $500 that I assume I'll never actually get paid. He doesn't show up at the track on Saturday to pay me but he does come the following Saturday with excuses. Then he says let's go double or nothing. I say I'm not going double or nothing on a 10-1 bet. So we agree to a bet of the $500 at 10-1, with me knowing I have nothing to lose as he won't pay me either way.

    With one second to go I have the $5,000 locked up and then the Bears make a field goal to get to 16. The Cubs had scored 16 so we push.

    I'm sure I'll never get the $500.

    So while I "win" $500 and should have "won" $5,000, it is still the worst bet I ever made, not because I know I won't get paid but because of my stupidity making the bet at all.

  2. #2
    Originally Posted by regnis View Post
    Funny story--at least I think it was funny. Last Thursday before the Bears- Packers game to open the season, I'm at the race track and some guy is carrying on all full of himself talking about the Bears and the Super Bowl and how great they are. I'm a big lifetime Bears fan but I don't share his view this year and think Trubisky is pretty bad. So he's going on and on and finally I say they'll be lucky to outscore the Cubs.

    Obviously, my statement is ridiculous hyperbole as a football team is always going to outscore a baseball team. So anyway he says I'll bet you anything you want that the Bears will outscore them. The smart thing to do would be to walk away, but I would rather blow $50 than walk away. So I tell him I'll bet $50 but I want odds. He says I'll give you $100-1 on as much as you want. I tell him he doesn't even have $5,000 if I were to win, so let's just make it 10-1.

    That day the Cubs get 10, the Bears get 3. So I win $500 that I assume I'll never actually get paid. He doesn't show up at the track on Saturday to pay me but he does come the following Saturday with excuses. Then he says let's go double or nothing. I say I'm not going double or nothing on a 10-1 bet. So we agree to a bet of the $500 at 10-1, with me knowing I have nothing to lose as he won't pay me either way.

    With one second to go I have the $5,000 locked up and then the Bears make a field goal to get to 16. The Cubs had scored 16 so we push.

    I'm sure I'll never get the $500.

    So while I "win" $500 and should have "won" $5,000, it is still the worst bet I ever made, not because I know I won't get paid but because of my stupidity making the bet at all.
    Haha, pretty ballsy bet....dont know the guy but Im guessing if he had won, hed have shown up at the track hounding you for his 50

  3. #3
    The worst winning bet I ever made was back in 2007. I have made maybe four or five college football bets on over or under regular season wins in my life. We bet Hawaii Over 11 1/2 wins that year. LOL.

    That bet probably took a decade off my life. The second game went into overtime. Another game went into overtime. And they squeezed by Nevada 28-26 late in the season. It was torture half the weeks. Then they played a bad Washington team in the finale, and they won 35-28.

    Too much wear and tear. And people would ask, "Let me get this straight. You have Hawaii OVER 11 1/2 wins?!?!?"

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