In this Article, I describe how Holmes, Hohfeld, and other legal realists deployed the jural character of the privilege status to debunk the libertarian narratives of “classical legal thought.” I then present three doctrinal areas in which contemporary American legal discourse seems to ignore these realist analytics by mistaking the privilege status for a private sphere of liberty rather than recognizing it as a state-imposed, legal relationship between parties. I conclude that the vitality of this error—reflected not only in the recent revival of explicit libertarian thought in constitutional and private-law scholarship, but also in the implicit starting point of much mainstream American legal doctrine—can be traced in part to the success of mid-twentieth century legal elites in domesticating the legal realist critique by framing realism in distinctly procedural and institutional, rather than substantive and ideological, terms. . . .