Abstract: This Article traces how and why the First Amendment has gone from a shield of the powerless to a sword of the powerful in the past hundred years. The central doctrinal role of “content neutrality” and “viewpoint neutrality” in this development is analyzed; the crucial tipping points of anti-Semitism, in Collin v. Smith, and pornography, in Hudnut v. American Booksellers, are identified. The potential for substantive equality to promote freedom of speech is glimpsed.