Oliver Wendell Holmes Jr.(Library of Congress / Silsbee, Case, and Co.)

Wounded three times during the Civil War—once when a bullet passed right through his neck—Oliver Wendell Holmes Jr. lived long enough to chat with Franklin Roosevelt just days after his inauguration. Henry and William James were close friends (Holmes was a pallbearer at the latter’s funeral); so too was Louis Brandeis. Alger Hiss served as one of Holmes’s many young law clerks. In 1902, Theodore Roosevelt appointed Holmes to the Supreme Court, where he served for three decades, after having sat on Massachusetts’s highest court for 20 years. A prolific correspondent, he wrote thousands of letters and, as a judge, nearly 2,000 opinions and dissents, many of which remain famous.

Yet despite his public persona and ample social skills, Holmes has always been a difficult subject for biographers. He was a very private man, and toward the end of his life he burned a good number of his letters and implored friends to do the same. Eventually he agreed to let Felix Frankfurter write a posthumous biography, which was then stymied by Frankfurter’s appointment to the Supreme Court. (Holmes retired from the court in 1932, at age 90, and died in 1935, just two days before his 94th birthday.) Frankfurter assigned the task to Mark DeWolfe Howe, one of Holmes’s former law clerks, whose father wrote a biography of Holmes’s father. But Howe never completed it; by the time of his own death in 1967, he had published only the first two volumes in a projected series, taking Holmes as far as 1882 and his appointment to the Massachusetts high court.

After Howe’s death, Holmes’s papers remained closed for almost two decades; they weren’t made available to the public until 1985, some five decades after their owner was interred in Arlington National Cemetery. Since then, there has been no shortage of biographical portraits, from Sheldon Novick’s Honorable Justice (1989) to G. Edward White’s Justice Oliver Wendell Holmes: Law and the Inner Self (1993) to Louis Menand’s Pulitzer Prize–winning The Metaphysical Club (2001) to Brad Snyder’s The House of Truth: A Washington Political Salon and the Foundations of American Liberalism (2017).

Now enter Stephen Budiansky, biographer of Charles Ives and author of such books as The Bloody Shirt: Terror After Appomattox and Code Warriors: NSA’s Codebreakers and the Secret Intelligence War Against the Soviet Union. In his discriminating, genial, and admiring new biography, Oliver Wendell Holmes: A Life in War, Law, and Ideas, Budiansky offers a credible introduction to the justice, whom he regards as a model of humanistic skepticism, someone willing to interrogate even his own most cherished premises and suppositions. To Budiansky, Holmes is a hero of American jurisprudence, partly because he was capable of learning from his mistakes. “To have doubted one’s own first principles,” Holmes once wrote, “is the mark of a civilized man.” Indeed, for Holmes, doubt was the only certitude. “When you know that you know,” he observed, “persecution comes easy.”

Born in 1841 to a family of Boston “Brahmins” (Oliver Wendell Holmes Sr. evidently coined that turn of phrase), the younger Holmes was raised in comfort and wealth. His father was a distinguished physician, teacher, and scientific writer who had published pioneering essays on everything from puerperal fever to photography and, at age 21, had composed the beloved poem “Old Ironsides.” Dr. Holmes had also proposed the name for a new magazine, The Atlantic Monthly, and contributed to it a series of witty articles, “The Autocrat of the Breakfast Table,” which he later collected into several popular books. Yet for all his sparkle and talent, there was something invincibly parochial about him: He once described Boston as the hub of the universe and insisted that “we never had a Bohemia in Boston, and never wanted it.”

Over six feet tall and far worldlier than his diminutive father, Holmes regarded him as something of a dilettante; and when Holmes père traipsed to the battlefield at Antietam to look for his wounded son and then wrote about the excursion for The Atlantic Monthly, Holmes fils felt disgusted and exploited. The gulf that opened up between the two was not just a family quarrel. It marked a larger rift between the generations: the older one optimistic, pumped up on moral certitudes and absolutist thinking, the younger one war-scarred, embittered, and often cynical. “The generation that carried on the war has been set apart by its experience,” Holmes stated in a Memorial Day speech in 1884.

His relationship with his mother, Amelia Jackson Holmes, the daughter of a justice on the Massachusetts Supreme Judicial Court, must have been equally complicated. He claimed to have inherited her melancholy and skepticism, a connection Budiansky doesn’t explore, though he does mention Holmes’s remark that, once in his youth, he went on a bender: “My father never let me forget this for weeks…. My mother, being a much wiser woman, never said a word. That hurt me much more.”

Still, Holmes enjoyed a childhood and adolescence of antebellum privilege, including idyllic summers at the family’s 280-acre country estate in western Massachusetts, which he fondly recalled 60 years later, noting that “among the foundations of my soul are granite rocks and barberry bushes.” At Harvard, he joined such exclusive social clubs as the Porcellian and yet found a way to maintain a flinty independence of thought largely inspired by Ralph Waldo Emerson. (“The only firebrand of my youth that burns to me as brightly as ever is Emerson,” Holmes remarked near the end of his life.)

But then came the war. “Life is a struggle,” Budiansky summarizes Holmes’s viewpoint after the war, “and it is the struggle that gives it meaning.” Serving for two years in the 20th Massachusetts Volunteer Infantry, Holmes was shot just above the heart at Ball’s Bluff and then in the neck at Antietam; sick with dysentery, he missed the fighting at Fredericksburg, where his unit suffered calamitous losses. At the battle known as the Second Fredericksburg, he was shot again, this time in the foot. After recuperating for eight months at home, he took a position in the Sixth Corps and witnessed the unspeakable carnage of the campaign known as the Wilderness, where the losses averaged, he calculated, about 3,000 a day. “How immense the butchers bill has been,” he wrote to his family. Discharged in 1864, he was forever changed. “I started in this thing a boy,” he said. “I am now a man.”

That Holmes’s wartime experiences later led him to dismiss the high-minded, unrealistic idealism that he associated with antebellum romanticism and to distrust, as Budiansky writes, “zealotry and causes of all kinds” has become a leitmotif in Holmes scholarship. He was also affected by the insights of the mathematician Chauncey Wright, one of the few intellectual influences Holmes acknowledged. Wright had shown him that “I must not say necessary about the universe, that we don’t know whether anything is necessary or not.” For Holmes, what was necessary was work, technical expertise, professionalism, and the law. “If we would be worthy of the past,” he advised the listeners of his Memorial Day speech, “we must find new fields for action or thought, and make for ourselves new careers.”

Increasingly convinced “that law as well as any other series of facts in this world may be approached in the interests of science and may be studied, yes and practiced, with the preservation of one’s ideals,” Holmes passed the bar in 1867 and was soon commissioned to revise the standard reference work Commentaries on American Law, the American version of William Blackstone’s Commentaries on the Laws of England. The result was Holmes’s magnum opus, The Common Law, which he published in 1881, just before he turned 40 (a self-imposed deadline).

Injecting science into the law and elegance into his prose, Holmes wrote that the law “is forever adopting new principles from life at one end, and it always retains old ones from history at the other.” It is not “a brooding omnipresence in the sky” but rather something that keeps pace with the “felt necessities of the time, the prevalent moral and political theories, intuitions of public policy, avowed or unconscious, even the prejudices which judges share with their fellow-men.” The law, in Holmes’s view, is a balancing act: It evolves and adapts and at the same time always endeavors to get things right.

By the time of The Common Law’s publication, Holmes had been married for nearly 10 years to Fanny Dixwell, a childhood friend. Often described as reclusive, she nonetheless managed the couple’s social life in Washington with a keen and sometimes caustic intelligence. Holmes relished attention and certainly got plenty of it from his many female friends, but there is no evidence that these amounted to anything more than flirtations. Fanny was not, it seems, long-suffering—just wisely tolerant of her often insensitive husband.

In 1882, Holmes left private practice to take a post at Harvard Law as the Weld Professor of Jurisprudence. But he abruptly resigned in a matter of months when offered a seat on the Massachusetts Supreme Judicial Court, where he presided over trials that exposed him to an increasing number of economic and labor conflicts. In the 1896 case Vegelahn v. Guntner, for instance, the owner of a furniture factory, Frederick Vegelahn, had fired George Guntner, the leader of the upholstery workers striking for higher wages. The workers picketed Vegelahn’s factory, and Holmes refused to halt the peaceful protest. When Vegelahn appealed, the full court reversed his decision.

Even though the court overruled Holmes, his long dissent, according to Budiansky, represents the intellectual basis of his thought about the role of law in society. “I think that the judges themselves have failed adequately to recognize their duty of weighing considerations of social advantage,” Holmes argued in a lecture the following year. “The duty is inevitable, and the result of the often proclaimed judicial aversion to deal with such considerations is simply to leave the very ground and foundation of judgments inarticulate, and often unconscious.” Or as Budiansky observes, “Avoiding the policy questions did not make judges impartial: it only disguised their prejudices.”

As previous biographers have noted, Holmes became an idol of progressives after he joined the Supreme Court. He firmly opposed using the 14th Amendment to protect, as one justice put it, “the most sacred rights of property.” Likewise, he opposed the court’s decisions to strike down state laws that mandated a minimum wage or the maximum length of a workday.

One such case was Lochner v. New York (1905). The state legislature had passed a law to regulate sanitation and the length of the workday in commercial bakeries, which were often in the basements of tenements. Joseph Lochner, a bakery owner who had been fined for keeping his workers beyond the 10-hour-per-day limit, appealed the ruling, and the Supreme Court overturned the state law, claiming that it interfered with the right to make a contract and thus endangered laissez-faire. Holmes dissented from the majority opinion, arguing that “a constitution is not intended to embody a particular economic theory, whether of paternalism and the organic relation of the citizen to the State or of laissez faire. It is made for people of fundamentally differing views.”

Progressives like Felix Frankfurter and Harold Laski applauded Holmes’s eloquent dissent in Lochner v. New York, but they were disappointed by his decision in Patterson v. Colorado (1907). When the court upheld the fine levied against a Denver newspaper for criticizing a decision by a lower court, Holmes noted that the Bill of Rights didn’t apply to the states. In his view, the government could constitutionally limit free speech if it was deemed “contrary to the public welfare.” He reaffirmed this view a decade later in Debs v. United States (1919), in which he voted to uphold the conviction of Eugene Debs for speaking out against World War I, and in Schenck v. United States (also in 1919), Holmes sustained the conviction of socialists who had distributed leaflets protesting the wartime draft, because wartime implied that a “clear and present danger” existed, which they had ignored. The progressives’ idol had feet of clay after all.

After Harvard faculty and alumni attempted to have Frankfurter and Laski fired for their political opinions and because they were Jews, Holmes revisited his position on free speech. In the landmark case Abrams v. United States (1919), which involved five anti-war radicals who had been sentenced to 20 years in prison for violating the Espionage Act, Holmes dissented. Refining his arguments about a “clear and present danger,” he wrote that the defendants’ speech had not put the war effort at risk. And even if it had, he declared himself in favor of a “free trade in ideas—that the best test of truth is the power of the thought to get itself accepted in the competition of the market…. That,” he added, “is the theory of our Constitution. It is an experiment, as all life is an experiment.”

Holmes’s judicial record was complicated and not always consistent. He joined the minority opposing the court’s decision in the trust-busting Northern Securities case, infuriating Theodore Roosevelt, but endorsed his imperialism when Holmes upheld the government’s position in the so-called Insular Cases, ruling that the people of annexed territories like Puerto Rico, Guam, and the Philippines did not have the rights of full US citizens. In a set of cases dealing with segregation in the South, he reaffirmed the “separate but equal” clause of Plessy v. Ferguson, which enshrined Jim Crow discrimination and helped gut the 14th Amendment of its equal-rights guarantee. Yet as a US Supreme Court justice, he argued in Moore v. Dempsey (1923) that the due-process rights of 12 black men had been violated when they were convicted of murdering a white man in Phillips County, Arkansas, after a mob opened fire on a meeting of black tenant farmers at a local church. (The trials of the 12 men each lasted less than an hour, with the juries returning verdicts in less than 10 minutes.) Holmes explained in the majority opinion, “No juryman could have voted for an acquittal and continued to live in Phillips County and if any prisoner by any chance had been acquitted by a jury he could not have escaped the mob,” thus rendering the state trials a sham.

Then, of course, there was the notorious Buck v. Bell decision (1927), in which Holmes supported the sterilization of Carrie Buck, an 18-year-old believed to be incapable of taking care of herself or her 7-month-old daughter, who seemed, according to a social worker’s testimony, “not quite normal.” “We have seen more than once that the public welfare may call upon the best citizens for their lives,” he wrote, doubtless alluding to the war in which his friends had died. “It would be strange if it could not call upon those who already sap the strength of the State for these lesser sacrifices.” He concluded his opinion with a chilling sentence: “Three generations of imbeciles are enough.”

To Holmes, the involuntary sterilization of those unable to care for themselves was a small price to pay for the larger defense of society. And his decision, while it does not make for particularly pleasant reading, does shed some light on the man who witnessed so many die on the battlefields of Antietam, Fredericksburg, Chancellorsville, and Spotsylvania. As he told a friend, “Every society rests on the death of men.”

Holmes was not a champion of individual rights. For him, living in society inevitably entailed what Budiansky calls some “brutal trade-offs.” And yet, in the end, Holmes believed that the law’s purpose was to balance incompatible and often iniquitous choices, a fundamental principle on exhibit in his dissent in Olmstead v. United States (1928).

In that case, the court denied the appeal of bootlegger Roy Olmstead, whose phone conversations had been tapped. Olmstead argued that he was protected by the Fourth Amendment’s injunction against unreasonable searches and seizures, but the court ruled that since federal agents had attached their taps to outside telephone wires, no unreasonable search or seizure had occurred. Holmes, however, found that the government had engaged in what he disdainfully called “dirty business.” Though it “is desirable,” he argued, “that criminals should be detected, and, to that end, that all available evidence should be used. It is also desirable that the Government should not itself foster and pay for other crime…. I think it a less evil that some criminals should escape than the Government should play an ignoble part.”

We may disagree with Holmes on many counts, as Budiansky certainly does. But in the end, there is something grand about the man. He was a seeker who strove to make the law just—or as just as possible in a fallible world populated by fallible people. He saw America as an unfinished experiment to which he was committed, and he viewed himself a pragmatist, and not in today’s sense of someone who wants to duck ideological fights or labels but rather as someone who endeavored to read the law realistically and with honesty and caution. Touched by fire, as he claimed he and his generation had been, Holmes had been hardened in the crucible of a civil war. Never claiming perfection for himself or others or for society, he too erred and allowed himself to be too subject to the felt necessities of the era. But he did what he could and sought at least to administer firm principle flexibly, and we would do well to remember him.