Personalist authoritarian leaders are a common presence in international politics. However, their ability to maintain power and navigate challenges varies significantly. This dissertation seeks to explain why some personalist authoritarian leaders remain in power longer than others. While previous studies on authoritarian survival have largely focused on structural factors, I argue that the ‘skill’ of the personalist leader also plays a crucial role. Specifically, I contend that the longevity of personalist dictators is influenced by their leadership skill, which can change over time, potentially diminishing their ability to handle crises. Drawing from political theory, comparative politics, international relations, political psychology, and business management literature, I propose a theoretical framework that defines 'skill' through four key traits: charisma, acumen, intimidation, and appeasement. These traits, I argue, are essential for extending a regime's survival – which includes managing different structural factors such as institutionalization, coupproofing, external alliances, and others. To test this theory, I examine the case of Muammar Qaddafi's rule in Libya, analyzing each decade of his leadership from 1969 to 2011. Through a qualitative content analysis approach, I utilize primary sources such as unclassified archival documents from the British Foreign Office, CIA Archives, Library of Congress, WikiLeaks, alongside interviews that I conducted with individuals who either met or worked with Qaddafi, to assess whether he was perceived as a skilled leader at different points in time of his rule. My analysis reveals that Qaddafi demonstrated all four leadership traits until 2010, after which his failure to exhibit appeasement arguably contributed to his downfall in 2011.