Using the United States Supreme Court’s 2019 rulings in Manhattan Community Access Corp. v. Halleck, Nieves v. Bartlett, and Iancu v. Brunetti as analytical springboards, this Article explores multiple fractures among the Justices affecting the First Amendment freedoms of speech and press. All three cases involved dissents, with two cases each spawning five opinions. The clefts compound problems witnessed in 2018 with a pair of five-to-four decisions in National Institute of Family and Life Advocates v. Becerra and Janus v. American Federation of State, County, and Municipal Employees. Partisan divides, the Article argues, are only one problem with First Amendment jurisprudence as the Court enters the third decade of the twenty-first century. Other troubles range from vehement disagreement in Nieves about crafting a federal rule impacting both speech and press rights to a split in Brunetti over when and how the Court should save a statute via a narrowing construction. Furthermore, perceived political partisanship separates the Justices today not only on the standard of scrutiny that applies in a case—Becerra and Janus rendered this vivid—but also on a case’s framing and the concomitant selection of precedent to steer the inquiry, as occurred in Halleck. Ultimately, the Article concludes that the rifts render free-expression jurisprudence even more muddled today than in the past. The Justices simply are not operating from the same First Amendment playbook. Worse yet, they function at times—particularly in cases such as Halleck—in a manner that strips away the increasingly thin veneer that personal ideologies are set aside when deciding cases.