This dissertation extends contemporary views about uncertainty. It does so through a reading of the role of uncertainty in the political thought of two modern philosophers, Baruch Spinoza and David Hume. Despite uncertainty's notable and multi-disciplinary appeal in the academic literature, the frame in which most scholars think about social and political uncertainty is one-sided. On the whole, contemporary scholars consider uncertainty as a problem in need of a remedy. In the social sciences uncertainty is transformed into risk in order to empirically calculate risk probabilities. The hope is that risks (uncertainties) can be controlled, reduced, and in all, mitigated. In this dissertation, I argue for a conceptual rethinking of uncertainty that expands its scope and reach to include a socially and politically beneficent understanding, a constructive form of uncertainty. In particular, I explore the ways social groups experience conditions of uncertainty in different contexts through an examination of what I term future-oriented and epistemic uncertainty in Hume and Spinoza's political thought. Spinoza's arguments for liberal democracy, and Hume's arguments favoring commercial society, are highlighted as instances of constructive uncertainty. The dissertation concludes by applying a general understanding of constructive uncertainty to the ideology of the American Dream in order to illustrate suggestively how a constructive conception of uncertainty might prove useful when critically engaging contemporary matters.