This paper follows the transformation of Kyrgyzstan’s president, Askar Akaev, over the course of the 1900s from an initial path of liberalization to more authoritarian tendencies. Akaev’s role in Kyrgyzstan’s post-Soviet trajectory is largely neglected in current scholarship, and this paper analyzes how the role of leadership compares with existing literature. This analysis focuses on how Akaev builds authority with various audiences and the constraints he had faced during his tenure. This paper explains the evolution of Akaev’s leadership strategy during 1989 to 1993 and then the period following the 1993 crisis, up to the present (2003). Next are given five alternative approaches to understanding the country’s trajectory over the 1990s and summarizes the benefits of incorporating leadership as a variable in understanding Kyrgyzstan’s transition. Finally, the president’s leadership helps to explain the country’s initial liberal path, but a full explanation of his shift to authoritarian tendencies must address other variables discussed in existing literature.