This Essay explores the Trump Administration’s unprecedented campaign targeting major U.S. law firms for retribution and examines such actions in light of the First Amendment’s relationship to these actions. Drawing on historical and doctrinal analyses, the Essay introduces and defends the concept of “legal speech” as a critical cluster of First Amendment protections encompassing the rights of lawyers to speak, associate, petition, and advocate on behalf of clients in an unfettered way and without government retaliation. Executive actions against Covington & Burling, Paul Weiss, Perkins Coie, WilmerHale, Jenner & Block, and Susman Godfrey purport to revoke security clearances, bar access to federal buildings, review hiring practices, and even penalize third-party clients doing business with the federal government—all in apparent response to these firms’ litigation stances, pro bono activities, and affiliations with political adversaries of the president. The Essay situates these actions within a larger historical, constitutional, and legal framework by tracing the doctrinal roots of legal speech through landmark Supreme Court decisions, including NAACP v. Alabama, NAACP v. Button, In re Primus, and Legal Services Corp. v. Velazquez, which collectively establish that legal advocacy—especially litigation aimed at advancing civil rights and challenging government action—is constitutionally protected expression. The Essay further analyzes how the Administration’s actions mirror past attempts by government to suppress disfavored speech through indirect pressure on third parties, a tactic the Supreme Court unanimously condemned in NRA v. Vullo as recently as May of 2024. The Essay also chronicles how some firms capitulated to administrative pressure without a formal Order issued against them, engaging in what historian Timothy Snyder describes as “anticipatory compliance,” further raising alarm about the erosion of rule-of-law principles. Ultimately, this Essay argues that these Executive Orders constitute clear content-based restrictions on legal speech and are therefore unconstitutional.