The requirement of fair equality of opportunity has become an indispensable element ingrained in contemporary liberal social democratic theories. It stands as a dominant ideology upheld by a great number of politicians and scholars to regulate the basic structure of society and to direct public policy formulation. In academic circles, it is fashionable to defend this principle in one way or another, but it is quite unpopular to argue against it. Unfortunately, the popularity and dominance of the principle do not lead to its tenability. In fact, the principle is entangled with a series of severe theoretical and practical problems. In his recent work, H. T. Engelhardt, Jr. has uniquely and sharply discerned those problems, which deserves our serious attention. In this chapter, I attempt, based on Engelhardt's insights and arguments, to provide a critical review of the principle. My focus will be on its disastrous implications for health care allocation as well as its baneful contribution to the erosion of the family.