At the end of J.M. Synge's The Playboy of the Western World, Christy Mahon departs for a cosmopolitan future at the very moment he demands personal and national sovereignty. This article examines why that conflicted gesture has proven so troubling in literary history. Christy's ambivalent combination of cosmopolitan ambition and nationalist sentiment stoked conflicts within the Celtic Revival, prompting the infamous riots that unfolded during Synge's 1907 premiere, and it continues to trouble Irish literary criticism. The figure of Christy Mahon challenges what audiences and critics think they know about cosmopolitanism and nationalism, especially as he is updated in recent Playboy adaptations for global stages.