A notable difficulty with biographies of judges and academics is that the professional writing of their subjects is often dull, even when their ideas are brilliant and precise. Outside In: The Oral History of Guido Calabresi doesn’t have this problem. Norman I. Silber lets Calabresi, now an influential judge and still an important legal theorist, speak to us in his own voice through interviews Silber has recorded. And what a voice it is: lively, charming, witty, and revealing. While the book is two volumes, it is never boring, in part because Calabresi has had such a varied life. He has been a scion of a distinguished Italian family, a poor child refugee in America, one of the two primary founders of the field of law and economics, the Dean of Yale Law School, and finally, a judge on the Second Circuit.

It might be feared that such variety would create a pudding without a theme. But two strong threads tie together Calabresi’s entire life. The first is that he constantly looks to create a synthesis from different, even opposed, qualities in himself and the world: He is a notable Italian but a passionate American egalitarian. He is Jewish but a Catholic convert. He sees law through the lens of economics but corrects economics through the lens of the law. Because he revels in the incongruous, he is a genuine liberal while remaining a man of the left. When he expresses as much pride in the Yale Federalist Society founders as in graduates who make a career in the public interest as “conventionally” understood, he reflects out-of-fashion academic liberalism. He is committed to the proposition that society can reach a better consensus through a synthesis of apparently antithetical ideals—and the university is, above all, the place where that synthesis can take place.

His scholarship also reflects a real synthesis of law and economics. One brand of interdisciplinary legal scholarship tries to reduce law to another discipline, explaining law in terms of economics, psychology, or politics and then often proposing a reform program dictated by that other discipline’s principles. Under that perspective, law has little, if any, autonomy. Calabresi emphatically rejects that view. For him, law illuminates economics as much or almost as much as economics illuminates law. Thus, when law declines to treat behavior as strictly rational, it may show us that there are natural quirks of our psyche, such as loss-aversion, that puts bounds to our rationality. That is a reason that Calabresi may be considered one of the forerunners of today’s behavioral economics.

Calabresi’s most famous law review article, One View of the Cathedral, also juxtaposes law and economics. There he considers abstractly the issue of what kind of rules protect entitlements, that is, interests created by law. To use an example in the article, if I want to own your house, I must buy it. That is a property rule, giving us the right to hold something unless we voluntarily relinquish it. If the government wants to take it, it must pay you just compensation for it—a liability rule. That kind of rule permits others to take our entitlement involuntarily so long as they are willing to pay an objective assessment of its value. We don’t allow insane or incompetent people to sell their houses—an inalienability rule. That rule makes it impossible to trade an entitlement at all under certain circumstances.

Some of the reasons for using one rule rather than another reflect economic considerations. The government gets the advantage of a liability rule for eminent domain presumably because buying property for large projects may lead to high transaction costs, like holdouts. Property rules are enough to grease the skids for private transactions, even as they instantiate classically liberal concepts of property rights. Inalienability rules reflect deep moral commitments to social protection. And Calabresi is fine with law being informed by non-economic values. Unlike the other great founder of law and economics, Richard Posner, he never defends a market in babies—an “efficient” solution for adoption.

The article then shows how property and liability rules would work in various situations depending, for instance, on whether an entitlement to pollute is given to the polluter or an entitlement to clean air to the subjects of pollution. As is characteristic of Calabresi, and suggested by the title’s emphasis on the singularity of its view, the article does not seek to be the last word on the subject. It has thus launched more articles than any other legal work I know, suggesting other rules, additional details, or analogies in other legal fields.

Calabresi is quite explicit about how his disparate work as a judge and an academic come together to create a distinctive approach. First, he is an author for two audiences. He writes for lawyers so that his opinion will provide guidance for the future. But he also thinks of the structure of the law—the kind of matter he explicated in One View—and he tries, in his writing, to move law toward coherence in a way academics may appreciate. But he recognizes that this synthesis does not permit the luxury of a purely academic approach. As a result, he often thinks incrementally as a judge, in ways that will resolve the case before him with a minimum of fuss.

That kind of respect for the traditional role of judging reflects the other wellspring of his life: He is an ardent institutionalist. He reflects that commitment when he explains his reasons for being a Catholic. He believes in God and needs an institution in which to exercise that belief. That adherence does not necessarily mean he believes all the “nonsense,” as he puts it, that the Church espouses. He has an Italian Catholic sensibility of the kind that explains why Protestantism, with its more rigid personal demands and constraints, never took hold in that nation.

His institutionalism was also the reason that he was the most successful Dean of the Yale Law School in the last half-century. He thought about hiring in terms of creating a place where brilliant people of fundamentally different views were in dialogue. For instance, he believes that the clashes between legal realists (those who thought that legal decisions were determined by facts outside the law) and the legal process school (those who thought that many decisions could be determined by the elaboration of law) gave way to a new synthesis in such figures as Yale’s Alexander Bickel. While Calabresi does not spell out this synthesis, an example is presumably captured in Bickel’s famous doctrine of the “passive virtues,” in which he urges that the Supreme Court should consider political factors outside the law in deciding whether and when to take a case, but then decide that case only according to a reasoned elaboration of the Constitution.

Calabresi also prides himself on being a respecter of other institutions as a federal judge. Some of the practices to which that impulse leads seem to me exactly right. For instance, he has been the leading judge on his circuit in pressing his colleagues to certify difficult state law questions to state courts. Under certification, state supreme courts will settle their states’ law and then federal judges will apply it. This process respects our key institution of federalism as well as taking advantage of the expertise of the state judiciary.

The impulse is also apparent, although less successful in my view, in his notion that in some cases federal judges should invalidate an old law, passed under different circumstances, but then uphold it if the contemporary legislature enacts it again. Here again, an underlying rationale is dialogue and respect for a coordinated element of government. But such a practice not so subtly gives the judge more power—to decide under vague criteria when to force a hard decision on another branch and void its rule in the interim. Without this easier course, the judge himself will have to bite the bullet and decide whether the law is constitutional once and for all.

One of the delights of this quasi-autobiography is the wry self-knowledge Calabresi brings. He tells with relish a story about his great-uncle lawyer, Armando Calabresi, a well-known advocate in Northern Italy. Guido thought Armando quite unattractive in appearance. Then when he returned to Italy on his honeymoon, an older woman seated next to him at the opera remarked that Guido was the spitting image of Armando!

He also admits to a streak of Machiavellianism. He is—in a sense—the reverse of the innocent abroad in Europe so dear to Henry James and other American novelists. He is the sophisticated European bringing worldly wisdom to America.

One area in which I wish he had more self-knowledge is in his views on campaign finance. He discusses at length his view that the First Amendment needs to be more egalitarian, by which he means that the Supreme Court should allow legislatures to prevent people from spending substantial amounts of money on political messages and candidates at least around election time. But Calabresi is an example of the gross inequality always generated by rights—in this case, the right to free speech. Through his lectures to thousands of the most important lawyers-to-be, not to mention his writings, he has far more influence on the course of our political and social life than some millionaire who wants to use his money to express his own views. Multiply that influence through all the mostly left-leaning professors in our universities and it dwarfs that of the rich in setting the political agenda. Money, as Calabresi himself recognizes elsewhere, often confers less power than status.

The book benefits immeasurably from the extensive notes that Silber, a professor at Hofstra Law School, provides at the end of each chapter in which Calabresi recounts his life. Sometimes Silber provides the context of the facts of a case that Calabresi decided. Sometimes he puts Calabresi’s scholarship in the broader trends of its times. Sometimes he gently corrects some misremembrance. Silber’s arrangement creates the very kind of running dialogue that Calabresi himself has fostered throughout his long and wide-ranging career.