Fifty years of effort in artificial intelligence (AI) and the formalization of legal reasoning have produced both successes and failures. Considerable success in organizing and displaying evidence and its interrelationships has been accompanied by failure to achieve the original ambition of AI as applied to law: fully automated legal decision-making. The obstacles to formalizing legal reasoning have proved to be the same ones that make the formalization of commonsense reasoning so difficult, and are most evident where legal reasoning has to (...) meld with the vast web of ordinary human knowledge of the world. Underlying many of the problems is the mismatch between the discreteness of symbol manipulation and the continuous nature of imprecise natural language, of degrees of similarity and analogy, and of probabilities. (shrink)