Actually, there is no difference in any of their probabilities to get anything. To be more clear, at the end of the final shuffle, no matter what is in any cup, they each have a 1/3 chance of obtaining whatever the best choice is, no matter the order. For all intensive purposes they can all simultaneously point to a cup and have whatever is in there. Because of this, the only thing left is to examine gain-loss ratio. The only disadvantage is to the seller. His gain-loss ratio is much lower than that of the other 2 people. He wants to sell for 800. He can gain only 200 by getting 1000, gains nothing from the watch, and loses 300 if he gets a cup with $500 (or loses 800 with an empty cup). The other two only lose 500 by picking an empty cup, otherwise they each can gain 300 (picking watch) or 500 (picking 1000). They all gain obviosly if they choose a cup with everything, but the seller gains only 1000, while the other 2 gain 1300 (watch + 500).