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A gripping intellectual history reveals how Oliver Wendell Holmes became a free‑speech advocate and established the modern understanding of the First AmendmentNo right seems more fundamental to American public life than freedom of speech. Yet well into the twentieth century, that freedom was still an unfulfilled promise, with Americans regularly imprisoned merely for speaking out against government policies. Indeed, free speech as we know it comes less from the First Constitutional Amendment than from a most unexpected source: Supreme Court justice Oliver Wendell Holmes. A lifelong skeptic, he disdained all individual rights, including the right to express one’s political views. But in 1919, it was Holmes who wrote a dissenting opinion that would become the canonical affirmation of free speech in the United States.