In this dissertation I advance an internal critique of John Rawls's conception of how a democratic society marked by profound, but reasonable pluralism might nonetheless regulate itself through to public use of reason so as to be stable for the right reasons. I argue that on two points Rawls's analysis lacks then necessary critical apparatus to specify a satisfactory resolution to his own concerns. First, it sustains a psychological deficiency in that it does not pay sufficient attention to the motivational character of the kinds of norms or values that structure his conception of democratic stability. Second, it sustains a normative deficiency in that it does not pay sufficient attention to the complex nature of the pluralism of values that must be negotiated in order to account for this stability. To demonstrate these deficiencies, I first reconstruct Rawls's project as a matter of navigating problems of alienation and reconciliation. Then, I invoke the assistance of Hegel's analysis of the "actualization" of the individual will from his Philosophy of Right as a strategy for analyzing the success or failure of a project or reconciliation. Employing this analytical strategy, I demonstrate that Rawls's conception of public reason harbors an inherently alienating tendency for those who are motivated by the moral ideal of reciprocity that defines public reason for Rawls and that this alienating tendency stands to give rise to problems of instability. That Rawls fails to recognize this source of instability demonstrates the conception's psychologically deficiency. Then, I propose under the heading of "reasonable reconciliation" a conception of a form of reconciliation that is possible on the Rawlsian model and a set of substantive political values (beyond the more formal values of freedom and equality of citizenship upon which Rawls focuses) that might reasonably be embraced from within public reason so as to render such reconciliation plausible. That the addition of such a set of values to the Rawlsian conception might make the difference between stability for the right reasons and instability demonstrates that the conception sustains a normative deficiency.