This paper explores some of the basic ideological tenets of former Iranian President Muhammad Khatami, showing how they prevented him from realizing his reform agenda. Ideological inconsistencies and ambiguities exposed Khatami and his allies to criticism from both conservatives and radical reformers. Consequently, many Iranians who once voted for Khatami and his allies boycotted the presidential elections of 2005, paving the way for a conservative to succeed Khatami as president of Iran.