This article examines three free speech cases decided by the Supreme Court in its past two Terms. The three cases – United States v. Stevens, Snyder v. Phelps, and Brown v. Entertainment Merchants Association – are somewhat unusual in the sense that the harms of the protected speech are clear. Unlike some number of free speech cases throughout the First Amendment’s history in which the official reaction to the speech was vastly disproportionate to the amount of harm, if any, that the speech might cause, these three cases all involve plausible responses to moderately plain speech-associated harm. In dealing with such cases, however, the Court seems hobbled not only by its unwillingness to confront the question of harm directly, but also by its lack of appropriate doctrinal or theoretical tools to differentiate various forms of harm. This article distinguishes among participant harms, as with the harms to animals in Stevens; listener harms, as with the harms to the family of Matthew Snyder when Snyder’s military funeral was the target of an anti-gay protest; and third-party or persuasion harms, as with the harms to those who might have been the victims of violence fostered or facilitated by the interactive violent video games that California had attempted to regulate. Distinguishing among this trilogy of harms may enable courts and commentators to understand and manage more effectively a First Amendment that properly protects speech not because it is harmless, but despite the harms it may cause.