This article attempts to explain the Czech Republic’s geopolitical vacillation between the West and East over the past three and half decades. We tie this behavior, where one orientation never prevails permanently, to the continuity of political elites from the communist to the post-communist periods. In addition to general relevance, we discuss its implications for the country’s recent reaction to the Russian invasion of Ukraine. The focal points of this analysis are the geopolitical discourses and practices of three consecutive presidents: Václav Havel, Václav Klaus, and Miloš Zeman, each marking a decade in the Czech presidential office. We provide a historical-structural context to show that the Czech case has been an important example of a small state with its security continuously compromised by the hierarchical penetrations of great powers: Nazi Germany, the USSR/Russia, and most recently, China and the United States. Yet, as we demonstrate, the Czech Republic cannot be considered a stereotypical victim with mixed-sovereignty agreements being imposed on it. We present the three presidents in their active roles of geopolitical architects vis-à-vis the great powers as well as the Czech government. Heuristically, we conceptualize presidential foreign-and-security activities as performative geoprostitution. We show that for Havel, the primary act of geoprostitution was institutionalizing a civilizational client-patron relationship between a small state and a superpower (the United States). In contrast, not only was Klaus and Zeman’s performative geoprostitution different due to its Eastern orientation, but it was motivated by their self-importance and desire to carve out political legacies and greased by corrupted business interests.