Though widely adopted since the European wars of religion in the 16th and 17th centuries, liberal solutions to the problem of tolerance continue to face difficulties over issues, such as abortion and religious freedom, where deeply held values and matters of governance intersect. In this dissertation I provide a new argument for political tolerance that is supported by a Lefortian conception of democratic political legitimacy. In the first half of the dissertation I argue that two forms of liberalism, public reason liberalism and liberalism of conscience, fail to adequately address the difficulties posed by religious pluralism. In its Rawlsian form, the former cannot answer a reasonable theocrat's demand for a right to participate in governance according to non-public reasons. While the latter approach avoids this difficulty by allowing for semi-sovereign religious communities within a liberal state, it cannot address intolerance that arises within such politicized religious communities. In the third chapter I provide a prudential argument for the practice of political tolerance. Drawing on the works of Machiavelli, I argue that a tolerant pluralist state is better able to identify new political difficulties because it can draw upon the situated knowledge of diverse groups within its population. Insofar as each group depends on the success of the state for its own wellbeing, it is in the best interest of all to tolerate the others. In the final chapter I supplement this prudential argument with a conception of political legitimacy, drawn from Claude Lefort's work, that can be endorsed by those who are asked to tolerate one another in spite of deep moral differences. By holding empty the `symbolic place of power,' modern democracy is able to sever the link between political legitimacy and a transcendent moral foundation. This breakage permits those who disagree about the source and meaning of political legitimacy to carry those disagreements into their political life, while demanding that all citizens be extended civil and political liberties. It has the added benefit of granting flexibility in addressing the source of intolerance--permitting new grievances to be raised as new sources of intolerance arise.