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This article jointly examines two legal biographies of two landmark First Amendment decisions and the justices who produced them. In The Great Dissent (Henry Holt and Co. 2013), Thomas Healy explores Oliver Wendell Holmes’s dissent in Abrams v. United States (1919), which arguably laid the cornerstone for modern American free speech jurisprudence. In The Progeny (ABA 2014), Stephen Wermiel and Lee Levine explore William J. Brennan’s majority opinion in New York Times v. Sullivan (1964) and the development and evolution of its progeny over Brennan’s remaining twenty-five years on the Court. The article then explores three ideas: 1) the connections …