E.H. Carr's political thought has recently evoked renewed interest among the scholars of international studies. For situating Carr within his own historical settings, these scholars have illuminated his intellectual affinities with Karl Mannheim and other contemporaneous thinkers. What remains unexamined is Carr's relation with Peter. F. Drucker, to whom Carr gave special acknowledgement in the preface of The Twenty Years' Crisis. This article intertextually reads their discourses for uncovering Carr's historico-philosophical awareness. Comparing his The Twenty Years' Crisis and Conditions of Peace with Drucker's The End of Economic Man and The Future of Industrial Man, it will be clear that, for both authors, (1) the crisis derived from the failure of traditional political philosophy, (2) no effective alternative was available in their time, and (3) the nature of the crisis was the loss of meaning in life. Carr's search for a sound moral foundation will prove to be relevant in this unstable late-modern world.