TO FATHOM JUST HOW out of place the subject of Stephen Budiansky’s new biography, Oliver Wendell Holmes: A Life in War, Law, and Ideas, would be on today’s Supreme Court, one need only compare him with the Justice who has left the most significant mark on the contemporary Court, the recently retired Anthony Kennedy. Both Holmes and Kennedy were Republican appointees who became unlikely if inconsistent heroes for progressives. But the similarities begin and end there. In all other respects, Holmes was the anti-Kennedy, and, as such, he could hardly be further from the direction that the Court, dominated by Kennedy’s swing vote, has taken in recent decades. Disillusioned by the carnage of the Civil War and captivated by the genteel social Darwinism of the late 19th century, Holmes was a skeptic about airy abstractions like “human rights” and “human dignity,” the latter a keystone of Kennedy’s jurisprudence. And where Kennedy went against his own politics in striking down conservative abortion and marriage laws, Holmes in turn voted to uphold progressive labor and economic regulations for which he had little esteem. “If my fellow citizens want to go to Hell I will help them. It’s my job,” he once put it — an attitude unlikely to resonate today either with liberals looking for a more robust check on the depredations of the Trump administration or with conservatives seeking a judicial overthrow of health care and gun control legislation.

Indeed, Holmes’s jurisprudence would be more than just an anomaly on the present Court; it would likely preclude him from being confirmed to it. He would likely fall in the dead center of a Roe v. Wade “litmus test”: pro-choice groups would be troubled by his skepticism toward unwritten constitutional rights and his consistent deference to state legislatures, while moralizing pro-lifers would be appalled at his flippant scorn for “sanctity of life” rhetoric. “Originalists” and “strict constructionists” in the mold of the late Justice Antonin Scalia would also find scant encouragement from Holmes, who rejected the notion of the Constitution as a set of “mathematical formulas” and preferred instead to describe it in living, organic terms. And partisans of all stripes would justly cringe at Holmes’s enthusiasm for forced eugenic sterilization, notoriously upheld in the case of Buck v. Bell with a rhetorical flourish that the Justice himself acknowledged as “brutal”: “Three generations of imbeciles are enough.”

Even the one constitutional right for which Holmes did make a valiant and celebrated stand is at something of a crossroads. Holmes’s dissent in Abrams v. United States, exactly a century ago, set forth with supreme eloquence what would become the classic rationale for freedom of speech under the First Amendment:

[W]hen men have realized that time has upset many fighting faiths, they may come to believe even more than they believe the very foundations of their own conduct that the ultimate good desired is better reached by 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, and that truth is the only ground upon which their wishes safely can be carried out. That, at any rate, is the theory of our Constitution. It is an experiment, as all life is an experiment.

The “marketplace of ideas” that Holmes envisioned in Abrams — a case involving what he dismissed as “the surreptitious publishing of a silly leaflet by an unknown man” — is now routinely invoked by the conservative Supreme Court in a very different context: restrictions on corporate political contributions of the sort struck down in Citizens United v. FEC. Nor, on the other hand, is Holmes’s free speech jurisprudence particularly amenable to much of the contemporary left. In recent years, campus activists have showed little hesitation in suppressing offensive or controversial speech. Holmes, though, would scoff, for instance, at the notion of “trigger warnings” for materials likely to incite discomfort or hostility. As he himself put it, “[e]very idea is an incitement.”

What, then, is the value of yet another Holmes biography at a time when his jurisprudence seems so distant from ours? It is at once the strength and the flaw of Budiansky’s biography that it largely elides the question. As one of the few nonlawyers to write a Holmes biography, Budiansky is more interested in Holmes the man than Holmes the jurist; in the titular “life in war, law, and ideas,” law comes third. Instead, Budiansky’s account highlights Holmes’s irrepressible joie de vivre, his unsurpassable literary style, and the sheer breadth of his nearly 94-year life. Holmes lived long enough both to meet an old John Quincy Adams, president from 1825 to 1829, and to hire as his clerk a young Alger Hiss, convicted of perjury related to espionage in 1950. He cut his teeth on the essays of his sometime-mentor Ralph Waldo Emerson, whom he still described at 90 as “the only firebrand of my youth that burns to me as brightly as ever,” and spent his final decades reading the likes of Woolf, Hemingway, Joyce, and Proust (the latter in the original French). He also cultivated intellectual and political acquaintances on both sides of the Atlantic ranging from the James brothers to William Ewart Gladstone, from Bertrand Russell to both presidents Roosevelt.

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The archetypal “Boston Brahmin,” Holmes was born in 1841 to the namesake father who coined that very phrase, and came of age even as his native city reached the zenith of its cultural and political power. When Holmes the elder dubbed Boston the “Hub of the Solar System” — a moniker that remains rather less justifiably in use today — he meant it to be ironic, but it might plausibly have been taken in earnest, too. Budiansky’s opening chapters paint a vivid and elegiac picture of a city that, for all its insularity and self-importance, was nevertheless justified in its self-conception as an American Athens. The years of Holmes’s youth were also a golden age of amateurism, in which the literary luminaries weren’t professional authors but rather physician-poets like the senior Holmes and former ministers like Emerson. It was also an atmosphere of intense moral idealism, which the young Holmes eagerly imbibed: as a Harvard undergraduate and fervent opponent of slavery, he once volunteered to serve as a bodyguard for Wendell Phillips, the radical abolitionist leader.

This earnest, cultured, reform-minded world came to a violent end on the battlefields of the Civil War, in which Holmes was wounded three times and narrowly escaped death. For the rest of his life, Holmes carefully preserved his bloodstained uniform, a pair of musket balls removed from his body, and a note on which he’d scrawled his name after being shot in the neck at Antietam. Budiansky offers a visceral and page-turning account of Holmes at war, and rightly follows the pathbreaking lead of Louis Menand’s The Metaphysical Club in portraying the experience as Holmes’s intellectual crucible. As Holmes himself reminisced in an 1884 Memorial Day speech: “Through our great good fortune, in our youth our hearts were touched with fire.”

That conflagration burned away many things for Holmes, chief among them his moral idealism. As Budiansky writes, quoting Menand, the war didn’t merely make Holmes lose his belief in abolitionism, “[i]t made him lose his belief in beliefs.” Morality and even winning the war ceased to be the purpose as the bloodshed dragged on; instead, Budiansky writes, “the only meaning left to the war was to do one’s job.” The practical courage of simply doing one’s job — or as Holmes sometimes phrased it, “jobbism” — lay at the heart of what he later called the “soldier’s faith,” epitomized by the dispassionate dedication of his fellow soldiers who gave their lives in a cause that many of them didn’t even believe in.

After the war, Holmes channeled his own soldier’s faith into the study and practice of law. He became an early champion of the competitive meritocracy that now rules American professional life. In place of the generalist Brahmin world he was born into, Holmes called for a “little army of specialists” (a telling military metaphor) to serve as the elites of a modern democratic society. Holmes’s ideal cadre of lawyers and other professionals would furnish “a perfect type of the union of democracy with discipline,” their authority derived not from caste or breeding but, as Budiansky puts it, “hard technical competence.” Holmes applied the same standard to his friendships. Appointed to the Supreme Court at a time when antisemitism was de rigueur both socially, among Boston and Washington elites, and institutionally, in higher education and major law firms, Holmes unreservedly embraced the intellectual camaraderie of brilliant leftist and liberal Jews such as Harold Laski, Walter Lippmann, Felix Frankfurter, and, above all, his fellow Justice Louis Brandeis.

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Reading Budiansky’s biography, it’s hard to miss the oedipal undercurrents of Holmes’s hardheaded “jobbism.” Describing the charming and garrulous Oliver Wendell Holmes Sr., whose “irrepressible flippancy” frustrated early promise in either medicine or literature, Budiansky quotes the devastating but accurate judgment of the critic V. L. Parrington: “He was always an amateur.” Holmes the younger, perpetually annoyed by his father’s lack of seriousness, later reminisced that he might have had a great career if only “he had had the patience to concentrate all his energy on a single subject” — precisely, of course, what Holmes the younger did when he enrolled at Harvard Law School and immersed himself in his studies with workaholic intensity.

Yet Holmes could never quite shake the belle-lettristic tradition he was born into. Budiansky mentions in passing that before enrolling in law school, Holmes had visited Emerson to discuss his career path and justify his choice of law over literature. But in opting to pursue a legal career, Holmes was not rejecting Emerson’s example so much as seeking to preserve it in a changed world. In a Harvard lecture titled “The Profession of the Law,” he praised the law as “the calling of thinkers,” the transcendentalism of a workaday world:

I say […] that a man may live greatly in the law as well as elsewhere; that there as well as elsewhere his thought may find its unity in an infinite perspective; that there as well as elsewhere he may wreak himself upon life, may drink the bitter cup of heroism, may wear his heart out after the unattainable.

The irony, of course, is that Holmes’s language in praise of legal professionalism is nothing if not literary. (It sounds as though it were lifted wholesale from Emerson’s own famous Harvard speech a generation earlier, “The American Scholar.”) It’s impossible to imagine anyone talking that way about the law today; it was hard enough to imagine even in Holmes’s time. Holmes carried the “literary amateur” label his entire life, and not merely because people confused him with his celebrity father. When he was appointed to the Court by Theodore Roosevelt in 1902, the New York Evening Post rather disdainfully deemed him “more of a ‘literary feller’ than one often finds on the bench.” On the Court, Holmes was often reluctantly obligated to tone down his writing style in order to win the concurrence of his brethren; it’s no coincidence that his most celebrated and distinctive opinions are almost all dissents. But Holmes continued to draw scorn for a perceived lack of seriousness. One contemporary academic dismissed him as “a man of letters” and “master of epigrammatic expression” whose epigrams were “either half-truths or not truths at all.” Those words would have cut deep: Holmes was, in effect, being told that he’d become his father.

Such a combination of legal professionalism and literary flair seems unrepeatable a century later, when the former has all but stifled the latter. Today, most judges — or more accurately, the freshly minted law school graduates whom they hire as clerks — write for an insular audience of legal academics, practicing attorneys, and other judges. Holmes’s opinions were pithy and mostly devoid of technical jargon; as he once put it, “One has to try to strike the jugular and let the rest go.” Most court opinions today are, as Holmes’s childhood friend Henry James described 19th-century novels, “loose, baggy monsters,” teeming with footnotes, case citations, and superfluous analysis, and often accompanied by multiple concurrences and dissents. (Holmes, despite his reputation as the “Great Dissenter,” dissented only sparingly.) Contemporary opinions recite talismanic formulas and concepts (“strict scrutiny”; “arbitrary and capricious”; “discrete and insular minorities”) with incantatory frequency. Holmes, channeling Emerson’s disdain for dead forms of all kinds, warned that “the minute a phrase becomes current it becomes an apology for not thinking accurately to the end of the sentence.”

To be sure, the decline in judicial rhetoric from Holmes to today may seem neither as precipitous nor as pressing as, say, the decline in presidential rhetoric from the Gettysburg Address to Donald Trump’s tweets. But a decline it is. Holmes is as distant from contemporary law in style as he is in substance. And if Budiansky is somewhat short on the latter point, he atones for it by amply showing that for Holmes as for all great writers, style and substance were in the end one and the same. “To have doubted one’s own principles,” as Holmes put it in a quote that Budiansky uses as an epigraph, “is the mark of a civilized man.” Whatever their precedential force and logical rigor, Holmes’s opinions are the mark of his civilization. They are essays in the true sense of the word, recording the twists and turns of a mind attempting to impose provisional order on a world in which “certainty generally is illusion, and repose is not the destiny of man.” Or, if one prefers, they are poetry as Robert Frost defined it: “[A] momentary stay against confusion.”

So, Holmes’s critics were right. He was indeed a “man of letters,” a thinker and writer who just happened to use the law as his medium. The Emerson of American law, he was at once the ultimate amateur and the consummate professional.

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Geoffrey Kirsch is a PhD candidate in the Harvard University Department of English, where he studies the intersections of literature and law in 19th-century America. He previously practiced law in Boston.