The confluence of Justice Stevens’ retirement from the United States Supreme Court and the five-year anniversary of Chief Justice Roberts’ ascension provides an opportunity for a new look at the familiar debate over the relative desirability of rigid rules and contextualized, fact-specific analysis in constitutional cases. In a trio of recent First Amendment cases, the Court has stated and applied, and then retreated from, strict doctrinal rules and the refusal to defer to congressional findings that normally accompany such rules. These cases raise anew the question of the appropriateness of such rules and their durability as meaningful constraints on courts confronting difficult fact patterns. To convert into a question Justice Souter’s defense of such rules: does deciding First Amendment cases based on ‚fairly strict categorical rules‛ really ‚keep[ ] the starch in the standards for those moments when the daily politics cries loudest for limiting what may be said‛?