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The adage that “hard cases make bad law” has venerable pedigree, echoed by such prominent jurists as Oliver Wendell Holmes, Jr., but its precise meaning and logic are not clear. This paper asks what the saying can mean and whether it is true. I clarify the possible meanings of the aphorism by precisely defining “hard” and “bad.” And I analyze the statement not only in the context of a judge making law by deciding a case (the context apparently assumed by the saying), but also in a judicial hierarchy where law is made by appellate courts reviewing trial courts. In the single-court context, there is no “hard cases make bad law” effect if all relevant case facts are incorporated into doctrine; but if some dimensions of facts cannot be explicitly reflected in the law, then hard cases are indeed more likely than easy cases to make bad law. In a judicial hierarchy, hard cases might make bad law even when doctrine reflects all relevant facts. That is so because of incentives for fact distortion when trial and appellate courts have different legal preferences and the trial court is better informed about facts. The law being made in this context is “bad” not just in deviating from the higher court’s ideal point but in the strong sense of being Pareto dominated—that is, there are laws that both courts prefer to the law being made. But the effect of hardness is not monotonic: The cases that are most likely to make bad law are intermediately hard—not the easiest cases but not the hardest cases either.