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This article critically evaluates the major judicial opinions on the law of contracts written by Judges Benjamin N. Cardozo and Richard A. Posner. Respectively, these judges are the first and third most influential judges on the subject measured by the frequency with which contemporary contracts casebooks reproduce their opinions. Exploring dozens of classic opinions of these judicial titans, the piece contrasts the philosophies and methods the two judges employ in wrestling with many fundamental challenges in contract law, from formation to performance to damages. The inquiry suggests that, using Isaiah Berlin's nomenclature, Judge Cardozo is the fox of American contract law while Posner is its hedgehog. Judge Cardozo displayed the thickly-textured doctrinalist, an optimizer of competing objectives; Judge Posner is a maximizer. (Accompanying tables report data on the contributions of the 15 most influential judges contributing to contract law.)

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