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Summary: A letter to Tacitus from Pliny the Younger discusses length and brevity in forensic oratory. Pliny appears to argue in favor of length, but the letter’s deliberate ambiguities illuminate his larger theme as the responsibility of judicial rhetoric to shape the senatorial audience’s ethical response to tyranny. Pliny’s rhetorical theory shares with Lacanian psychoanalysis a therapeutic goal: subjects’ recognition of their relationship to the law as one of desire, free by virtue of their own (paradoxical) choice of subjectivity. This paper offers a theory of Pliny’s dialogic rhetoric as a kind of ‘talking cure’ rooted in the Socratic elenchus, and a historical example of the negotiation of the ‘forced choice’ proposed by Lacan in Seminar XI. It proposes the value of Lacan’s further conceptualization of the subject-Other relationship in terms of ‘traversing the fantasy’ for interpreting subjectivity in the particular circumstance of political tyranny.