What follows is an original case study of our First Amendment law of free expression and how it is created by the Supreme Court. Drawing heavily on heretofore unpublished internal papers from the chambers of Justice William Brennan and other Justices, this Article reveals how the 1964 landmark decision in New York Times Co. v. Sullivan was once in serious jeopardy of being overruled. In the course of this discussion, and in their examination of the evolution of the Court’s decision in Dun & Bradstreet v. Greenmoss Builders (1985), the authors describe and analyze: (1) how and to what extent the holdings in Sullivan and Gertz v. Robert Welch, Inc. (1974) came to be reconsidered; (2) how the nature of the expression at issue in Greenmoss Builders factored into the examination of this defamation case and changed the way the First Amendment limits the common law of defamation; (3) how the members of the Burger Court considered the question of the media versus non-media status of a defendant in a defamation case; (4) how the Justices grappled with the question of the legitimacy under the First Amendment of presumed and punitive damages awards in defamation actions; (5) how the issue of the difference between private speech and public speech came to take on constitutional significance; (6) whether the Court should reconsider the balance it struck in Sullivan between the public’s interest in being fully informed about public officials and public affairs and the competing interest of those who have been defamed in vindicating their reputation; and (7) how all of this ultimately influenced and determined the outcome in Greenmoss Builders. In the swirl of this discussion and examination of the historical record, the reader gets a rare glimpse of the inner workings of the Court and its clerks along with a better appreciation of how consensus is built and lost, replete with occasional barbs. Moreover, this Article reveals just how laborious the shaping of First Amendment doctrine can be, given the issues (some never fully discussed in published opinions) raised by the Justices in their consideration of the Greenmoss Builders case. In these respects and others, this Article informs the reader of some of the central (albeit internal) moments in the history of defamation law following Sullivan and thereby sheds new light on how the law in this area might be shaped in the future