You are sampling from an infinitely deep population, namely all rolls of the fair die. While you, Rick, will win 5/6 of the time and lose only 1/6 of the time, your expected return is the same on a single roll as it is on a zillion rolls. That return is (5/6)*$100 + (1/6)*(-$1000) or -$83.33.Therefore, it seems to me, it is not a good idea for Rick to take the bet if his aim is to make money on that roll.I'm sure you guys have discussed subjective aspects, and also things like how deep each player's pockets are. But for the limited question you ask, the key point is that the expected return per roll is the same whether it is one roll or many.
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