I was just out of a $ 3 million dollar winning streak – Around the same time as my weight loss bet I also had a long-running side bet with Tobey Maguire. Tobey and I are proud to see who can win the most sessions in a row without losing a single one.
I was just out of a $ 3 million dollar no-loss winning streak when we decided to go for a modified version of the old “last longer” bet. The stakes are $ 25k to see which of us can win the most out of 10 sessions.
This little side bet excites our competitive spirit and will prove to be a good bet for both of us in the long run… although I think Tobey ended up enjoying it more than he should have. I remember Molly Bloom asking me why I cared so much about the $ 25,000 side bet with Tobey when she and I won hundreds of thousands of dollars per session every time we played over to Dinastipoker. I explained that this isn’t about money, it’s about enjoying a little of your old pride, your old friend who doesn’t show up often, and can rub it all over his face for good.
And believe me, Tobey likes ribs more than I do. With Tobey, betting was never that simple as he insisted on setting all sorts of little parameters that would obviously be in his favor. For example, he likes to be late to games and always leaves at certain times. I, on the other hand, will show up early enough to see the first hand being dealt and if the game is good I’ll be playing until the sun rises as long as I know I’m getting the best of it.
Knowing this, Tobey drew up a rule stating that win or lose only applies as long as he arrives, and the bet must end when either of us stops that night or 11pm, whichever comes first. He knows that I will always play longer than him, so If I happen to be down one night when he decides to leave, even if I win late in the session it will only count based on whether I go up or down when he calls it a night.