Abstract: This Article traces two interwoven jurisprudential genealogies. The first of these focuses on the emergence of neutrality in speech and press doctrine. Content and viewpoint neutrality are now the bedrock principles of modern First Amendment law. Yet the history of these concepts is large-ly untold and otherwise misunderstood. Scholars usually assume that expressive-freedom doctrine was mostly undeveloped before the early twentieth century and that neutrality was central to its modern rebirth. But this view distorts and sometimes even inverts historical perspectives. For most of American history, the governing paradigm of expressive freedom was one of limited toleration, focused on protecting speech within socially defined boundaries. The modern embrace of con-tent and viewpoint neutrality, it turns out, occurred only in the 1960s as the Supreme Court merged earlier strands of rights jurisprudence in novel ways. The emergence of neutrality, this Article shows, was more gradual, more contested, and more contingent than we now assume. Re-covering this history reveals the novelty of the modern neutrality paradigm and casts new light on the history of other First Amendment concepts, like prior restraints, low-value speech, and over-breadth.