Commentators of the judicial decisions of Justice Holmes have often situated the decisions inside the doctrines of freedom of expression and the rules and tests approach to legal analysis. This Paper situates his judgments in the context of a political theory. Drawing from his articles, lectures and correspondence, the Paper highlights Holmes’ reaction to the idealism and rationalism of the intellectual current before him. His view of human nature, conditioned by his war experience, is elaborated. The Paper especially examines his theory of political struggle with the process-oriented view that the dominant social groups invariably become the political elite. The Paper then connects his theory of human nature to his legal doctrines, the role of the judiciary, the nature of the state, and a legal right.