This article concerns questions of artistic and literary freedom surrounding the Ulysses cases. My interest is how the courts responded to censorship charges once they were leveled, or more particularly, how and why they failed to respond in a mindful way. That is, why did they fail to bring anything that can be recognized as the rule of law to the issues raised in the contests before them? Where did American courts find the law? What weight did they give to the right to speak and publish? What conditions, in addition to the skills of Morris Ernst, contributed to the federal rulings that freed Ulysses, rulings that began (but only began) a decades-long retreat from the Hicklin straitjacket and toward greater artistic and literary freedom? To understand the Ulysses cases it is necessary to appreciate their antecedents, especially the Hicklin decision in England and three subsequent obscenity prosecutions (two state and one federal) in nineteenth-century New York. These four cases are discussed next. The Article then moves to its two main acts: the prosecution of Anderson and Heap and the federal court decisions that allowed Random House safely to publish Ulysses in the United States. The second of these federal decisions, from the Second Circuit Court of Appeals, may be seen as the progenitor of modern obscenity law. Less prominent cases in the story are examined throughout.