This Essay explores the connections between Justice Holmes’s ideas about law practice and his jurisprudence. What we discover, or so I will argue, is an unfamiliar Holmes–a Holmes whose arguments differ in important respects from the standard positivist and realist ideas that later generations read back into The Path of the Law. I want to suggest that reading Path as proto-Hart, proto-Frank, or proto-Cohen distorts a good deal of what Holmes actually says. In my view, Holmes’s penchant for radical rhetoric leads him to overstate the conclusions that he actually means to establish and lands him in fallacies that I explore in some detail. Holmes had a more moralistic picture of lawyers and clients than his own tough talk suggests, and I will suggest that this accounts for the fallacies. In short, reading Path as an implicit definition of the good lawyer helps us distinguish the sound from the specious in the essay’s jurisprudence.