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Let me throw in here what Rawls might reply to this objection. He considers something very much like it in his Theory of Justice. Basically he says that a situation like this will not arise. And let's bear in mind that the parties in the Original Position have a general knowledge of how human societies work, and they know that this sort of case is not going to occur. He makes the following statement:

Yet it seems extraordinary that the justice of increasing the expectations of the better placed by a billion dollars, say, should turn on whether the prospects of the least favored increase or decrease by a penny....Part of the answer is that the difference principle is not intended to apply to such abstract possibilities. As I have said, the problem of social justice is not that of allocating ad libitum various amounts of something, whether it be money, or property, or whatever, among given individuals. Nor is there some substance of which expectations are made that can be shuffled from one representative man to another in all possible combinations. The possibilies which the objection envisages cannot arise in real cases; the feasible set is so restricted that they are excluded. [Rawls, Theory of Justice p. 157-8]

When Rawls says that such cases cannot occur, I think he means that there will always be other options available that are beneficial to the more affluent and also beneficial to the last advantaged group.