When he was appointed to the Supreme Court in 1902, at the age of sixty-one, he was best known to the general public as the son of a famous poet and man of letters; when he retired, thirty years later, he had been called "the greatest of our age in the domain of jurisprudence, and one of the greatest of the ages." Oliver Wendell Holmes's thirty years on the Supreme Court unquestionably made his reputation, and yet those years, given the aspirations of Holmes's earlier career, were years in which his mood as a judge can best be described as resignation. He was not able to achieve anything like what he thought he could achieve as a judge; regularly he confessed his inability to do anything other than ratify "what the crowd wants." He wryly suggested that on his tombstone should be inscribed "here lies the supple tool of power," and he allegedly told JOHN W. DAVIS that "if my country wants to go to hell, I am here to help it." For these expressions of resignation he was called "distinguished," "mature," and "wise," the "completely adult jurist." The constitutional jurisprudence of Holmes could be called a jurisprudence of detachment, indifference, or even despair; yet it was a jurisprudence in which contemporary commentators reveled.
Holmes's career hardly began with his appointment to the Court. He had previously written The Common Law, a comprehensive theoretical organization of private law subjects, taught briefly at Harvard Law School, and served for twenty years as a justice on the Massachusetts Supreme Judicial Court. Although he had not considered many constitutional cases as a state court judge, he had a distinctive philosophy of judging. There was little difficulty in the transition from the Massachusetts court to the Supreme Court; Holmes simply integrated a new set of cases with his preexistent philosophy. That philosophy's chief postulate was that judicial decisions were inescapably policy choices, and that a judge was better off if he did not make his choices appear too openly based on the "sovereign prerogative" of his power.
Arriving at that postulate had been an unexpected process for Holmes. He was convinced, at the time he wrote The Common Law (1881), that private law could be arranged in a "philosophically continuous series." His lectures on torts, criminal law, property, and contracts stressed the ability of those subjects to be ordered by general principles and the desirability of having judges ground their decisions in broad predictive rules rather than deferring to the more idiosyncratic and less predictable verdicts of juries. Holmes had accepted a judgeship in part because he believed that he could implement this conception of private law. Academic life was "half-life," he later said, and judging gave him an opportunity to "have a share in the practical struggle of life."
In practice, however, Holmes found that the law resisted being arranged in regular, predictable patterns. Too many factors operated to create dissonance: the need for court majorities to congeal on the scope and language of a decision; the insignificance of many cases, which were best decided by routine adherence to precedent; the very difficult and treacherous policy choices truly significant cases posed, fostering caution and compromise among judges. The result, for Holmes, was that legal DOCTRINE developed not as a general progression toward a philosophically continuous series but rather as an uneven clustering of decisions around opposing "poles" that represented alternative policy judgments. "Two widely divergent cases" suggested "a general distinction," which initially was "a clear one." But "as new cases cluster[ed] around the opposite poles, and beg[a]n to approach each other," the distinction became "more difficult to trace." Eventually an "arbitrary ? mathematical line" was drawn, based on considerations of policy.
Thus judging was ultimately an exercise in making policy choices, but since the choices were often arbitrary and judges had "a general duty not to change but to work out the principles already sanctioned by the practice of the past," bold declarations of general principles were going to be few and far between. Indeed in many cases whose resolution he thought to turn on "questions of degree," or "nice considerations," or line drawing, Holmes attempted, as a state court judge, to avoid decision. He delegated "questions of degree" to juries where possible; he relied on precedents even where he felt that they had ceased to have a functional justification; he adhered to the findings of trial judges; he resorted to "technicalities" to "determine the precise place of division." And on those relatively few...