The thesis that the theory of charismatic-plebiscitary democracy developed by the liberal Max Weber in the wake of the Weimar Republic was developed to its ultimate consequences by the anti-liberal Carl Schmitt in the final crisis of the first German democratic experience has been hotly debated since it was first advanced in the late 1950s. This paper proposes a fresh look at the controversy. By comparing both authors’ concepts of politics in their relation to the problem of modernity, it argues that the Weber-Schmitt affinity is neither a groundless legend nor a case of necessary continuity. Given the intrinsic tensions of Weber’s concept of politics and of his narrative of modern rationalization and secularization, as opposed to the relative internal coherence of Schmitt’s assertion of “the political” against modern liberal politics, the paper contends that the relationship between the two authors should be understood in terms of a contingent affinity.