Hustler Magazine Inc. v Falwell was a 1987 landmark case that expanded the scope of First Amendment protections. The Supreme Court ruled that a publication made by Hustler magazine was constitutionally protected, despite containing material that vehemently disparaged televangelist Jerry Falwell. Significantly, this case limited the ability of public figures to recover damages for infliction of emotional distress. Though the Court had previously qualified the extent of free speech, it declined to do so in this instance because factors such as precedent, the history of First Amendment applications, and the consequences of a ruling adverse to Hustler each weighed in the magazine’s favor. This paper analyzes primary sources including oral arguments and Court opinions to demonstrate why Falwell lost the case. In particular, both sides’ arguments are examined through the analytical frameworks established in Philip Bobbitt’s Constitutional Fate, a work which describes multiple avenues for assessing the constitutionality of laws.