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Considerable scholarly work has examined the transition to democracy. In this paper, we investigate a path to democracy that is very different from that typically described. During the Archaic period (800-500 BCE), many Greek poleis (city-states) replaced aristocracies with a more narrow governing institution--an autocrat known as the tyrant. Yet as classical scholars have noted, many of the poleis where tyrants reigned in the Archaic period became among the broadest democracies in the subsequent Classical period (500-323 BCE). We analyze a data set of ancient Greek political regime types and review the history of the best-known Archaic period tyrants in order to explore why a transitory narrowing of power--Greek tyranny was a transitory institution--can set the stage for democratization. We briefly consider other historical and modern examples. Our paper shows why an understanding of progress toward democracy requires recognizing the potential importance of nonmonotonic transition paths.