This article reads Lionel Trilling’s 1947 novel, The Middle of the Journey, through postwar controversies about the relationship between law and conscience. The 1945–46 Nuremberg Trials divided American liberals, who disputed whether fascism was best combated by fidelity to the rule of law or by a more skeptical relationship to legal authority. The Middle of the Journey explores this question through debates about the Moscow Trials, Herman Melville’s Billy Budd, and a controversial local crime. Drawing on archival research, the author argues that Trilling sought to depict a dialectical relationship between the efficacy of law and the urgency of conscience. The novel’s attention to legal institutional forms ultimately challenges the view that Trilling was hostile to practical politics and offers insights for liberals and leftists interested in working with, or through, the law.