Charismatic leaders who see countries through critical junctures of institutional genesis have an unusual amount of freedom in designing institutions and shaping the political landscape of their country for years to come. This paper looks at the cases of Turkey and Tunisia, two countries that were led through the period of institutional design by charismatic leaders Mustafa Kemal Atatürk and Habib Bourguiba, respectively. It seeks to discover why these countries went on different political paths, despite remarkably similar historical and political circumstances. Turkey became a multiparty democracy mid-century, about a quarter century after its foundation, whereas Tunisia had an authoritarian regime in place from its independence in 1956 until now. Using both secondary sources and archive data for a comparative case study, this paper argues that the fact that Atatürk embedded his charisma in institutions and shared power with a band of followers created conditions that were highly favorable to an eventual transition to democracy. On the other hand, Bourguiba exercised power through strictly patrimonial channels and did not invest in institutions. He also interacted with followers on a patron-client basis and through a hub-and-spoke structure that kept elites separate and competing for influence. This meant that his successor Ben Ali was free to begin his own personal rule without the constraints imposed by institutions or a unified body of elites. In the absence of a personal commitment to democratization on the part of Ben Ali, along with that of a strong civil and political society, Bourguiba's choices led to the robustness of authoritarianism in Tunisia.