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Can democracies cope with exceptional circumstances or radical contingencies while remaining committed to the democratic principles of political equality, majority rule, and respect for pluralism and opposition? In this paper, I explore an important challenge in advocating for democratic procedures to manage radical contingencies. This challenge revolves around the historical consensus, across opposing traditions, regarding the granting of highly-concentrated and discretionary decision-making powers to a single individual, allowing them to surpass regular procedures in such circumstances. Figures like Machiavelli, a republican, advocated for a magistracy of dictatorship; Locke, a liberal, defended prerogative power; and Mill, a proponent of representative government—a porto-democrat—permitted temporary dictatorship to address radical contingencies. While they imposed conditions on the exercise of such power—namely, the strength of the constitution, pursuit of the public good, and preservation of freedom—these conditions are often challenging to precisely define and agree upon. Consequently, preventing the arbitrary exercise of highly personalized power becomes difficult. Machiavelli and Locke are extensively debated concerning the issue of radical contingency or the 'state of exception.' However, often the focus is on its implications for the rule of law, questioning whether the sovereign can act outside and even against the formal prescriptions of the law. While I touch upon these aspects, I also aim to underscore the centralization of power in their accounts, which contradicts the principles of democracy. Ultimately, I seek to demonstrate that to preserve democracy during exceptional circumstances, it is not enough to use Schmitt as a foil but a profound paradigm shift challenging predominant schools of thought is necessary.