This Article addresses the argument that certain aspects of copyright law violate the First Amendment—an argument numerous copyright and constitutional law scholars advance—from a historical perspective. The Federal Courts have largely rejected versions of this argument, although in the wake of the Eldred v. Ashcroft decision there is some small indication that they are more willing to apply First Amendment doctrine to copyright cases. Most of the literature addressing the relationship between copyright law and the First Amendment approaches the question from either a doctrinal or an originalist perspective. Both perspectives face large problems. The doctrinal angle must contend with the large body of case law refusing to apply the First Amendment to copyright infringement suits, while the originalist perspective struggles with the lack of evidence of the intent of the ratifiers with respect to the relationship between the two clauses. In response to these two approaches, this Article argues that in order to understand the current tension between the First Amendment and the Copyright Clause, it is necessary to go beyond the founding generation and investigate the way both copyright and the First Amendment were transformed by the generation that lived through the period surrounding the Civil War and ratified the Fourteenth Amendment. Furthermore, because of the importance of historical struggles to the interpretation of the First Amendment, it is helpful to step outside the courtroom in order to understand the values that animate the Free Speech Clause. An understanding of this history clarifies the constitutional values embodied in the Copyright Clause and the First Amendment, and thus offers textual and historical grounding for the arguments that there is a tension between the two clauses that must be reconciled.