If Rawls were to consider that perhaps the losses felt by the rich may indeed outweigh the benefits felt in return and also outweigh the gain in happiness of the poor, then I wonder how solid he would feel his argument is. Rawls bases his difference principle on the assumption that wealth is a natural asset that people gain it by being in the right place at the right time. The idea that wealth is something that is only inherited and cannot be gained on ones own would surely bring into question fairness and would most likely end in the conclusion that all should be made equal.
In the real world however, hard work and ambition can achieve wealth. In this real world scenario then, it is reasonable to believe that the poor could be poor not always because of a natural lottery, but often because of their refusal to put forth the effort to be otherwise, though I accept many may differ with this view. Thus it is also true that the rich could be rich in many cases because of their willingness to study hard and train from an early age. It is for these reasons that I, at times, feel that Rawls' difference principle actually has little to do with fairness. ...
Those on high incomes are in such a position because other citizens have voluntarily given or exchanged their wealth or resources in return for a service provided. Restricting the right of those with resources to do as they wish with them is a restriction on freedom, and so contradicts Rawls' first and what he feels is the most important principle of liberty. Apart from doubts on Rawls' difference principle, a key problem for him is to show how such principles would be universally adopted, and here the work borders on general ethical issues. According to Rawls, we cannot simply assume that society will automatically regulate itself in such a way that the principles followed are just. Some members of the society will be in more powerful positions than others, and as a result will try to shift the principles to their own advantage. (Rawls, 1971, 77-83)
In order to combat this problem, Rawls introduces a theoretical "veil of ignorance" in which all the "players" in the social game would be placed in a situation which is called the "original position." (Rawls, 2001, 161-65) By this he means that all deciding parties in establishing the guidelines of justice must approach the task with no knowledge of their status, wealth, natural abilities or any other aspect of themselves to which they could render advantages in laying out the principles. For example, if everyone in this society has an equal amount of influence toward the establishing of specific laws, a rich man may propose that taxes should be equal for all rather than proportionate to ones assets. It is for this and similar situations that Rawls feels that everyone must become oblivious to