This article is a critique of the Dworkinian theory of fairness in the context of Affirmative Action. Although Dworkin committed tremendous endeavors in an attempt to give a fairness argument backed by an empirical study, the question of whether affirmative action is fair remains inconclusive. The sample used in the study is unrepresentative, and the results are open to interpretation. If legitimacy and fairness of a policy is a matter of the fit between the theory and the practical consequence, would the change of racial composition within the country, such as the increasing number of immigrants, and the change of a country's role in the international community, such as globalization, affect the current meaning of diversity? Moreover, although diversity seems to be a reasonable goal, Dworkin failed to make a strong case for why specially admitting Blacks into elite universities is essential for justice. Also, the question of fairness remains unanswered because the lesson of Singapore and Malaysia shows that the general interest of society is not warranted by a policy of sacrificing a few people.