Writers on Holmes have forgotten just how influential poetry and literature were to him, and how powerfully literary his Supreme Court dissents really are. The son of the illustrious poet by the same name, young Holmes, or Wendell, fell in love with the heroic tales of Sir Walter Scott, and the “enthusiasm with which Holmes in boyhood lost himself in the world of Walter Scott did not diminish in maturity.” Wendell was able to marry his skepticism with his romanticism, and this marriage, however improbable, illuminated his appreciation for ideas past and present, old and new. “His aesthetic judgment,” says Mark DeWolfe Howe, author of the most definitive biography of Holmes and one of Holmes’s former law clerks, “was responsive to older modes of expression and earlier moods of feeling than those which were dominant at the fin de siècle and later, yet his mind found its principle nourishment in the thought of his own times, and was generally impatient of those who believe that yesterday’s insight is adequate for the needs of today.” Holmes transformed and adapted the ideas of his predecessors while transforming and adapting—one might say troping—milestone antecedents of aestheticism, most notably the works of Emerson. “[I]t is clear,” says Louis Menand, “that Holmes had adopted Emerson as his special inspiration.”
Classically educated at the best schools, Wendell was subject to his father’s elaborate discussions of aesthetics, which reinforced the “canons of taste with the heavier artillery of morals.” In addition to Scott, Wendell enjoyed reading Sylvanus Cobb, Charles Lamb’s Dramatic Poets, The Prometheus of Aeschylus, and Plato’s Dialogues. Wendell expressed a lifelong interest in art, and his drawings as a young man exhibit a “considerable talent.” He declared in his Address to the Harvard Alumni Association Class of 1861 that life “is painting a picture, not doing a sum.” He would later use art to clarify his philosophy to a friend: “But all the use of life is in specific solutions—which cannot be reached through generalities any more than a picture can be painted by knowing some rules of method. They are reached by insight, tact and specific knowledge.”
At Harvard College, Wendell began to apply his facility with language to oft-discussed publications in and around Cambridge. In 1858, the same year that Dr. Oliver Wendell Holmes Sr. gifted five volumes of Emerson to Wendell, Wendell published an essay called “Books” in the Harvard undergraduate literary journal. Wendell celebrated Emerson in the piece, saying that Emerson had “set him on fire.” Menand calls this essay “an Emersonian tribute to Emerson.”
Holmes had always admired Emerson. Legend has it that, when still a boy, Holmes ran into Emerson on the street and said, in no uncertain terms, “If I do anything, I shall owe a great deal to you.” Holmes was more right than he probably knew.
Holmes, who never gave himself over to ontological (or deontological) ideas about law as an existent, material, absolute, or discoverable phenomenon, bloomed and blossomed out of Emersonian thought, which sought to “unsettle all things” and which offered a poetics of transition that was “not a set of ideas or concepts but rather a general attitude toward ideas and concepts.” Transition is not the same thing as transformation. Transition signifies a move between two clear states whereas transformation covers a broader and more fluent way of thinking about change. Holmes, although transitional, was also transformational. He revised American jurisprudence until it became something it previously was not. Feeding Holmes’s appetite for change was “dissatisfaction with all definite, definitive formulations, be they concepts, metaphors, or larger formal structures.” This dissatisfaction would seem to entail a rejection of truth, but Emerson and Holmes, unlike Rorty and the neopragmatists much later, did not explode “truth” as a meaningful category of discourse.
Emerson and Holmes were “strong believers in the impulse to transcend limits,” Emerson by articulating and enabling the imaginative and productive intellect, Holmes by articulating and enabling an adaptive legal system. As if shaping their own poetics, these men transitioned or transformed “stable or coherent identities and meanings into formal and linguistic processes that continuously negotiate identities and meanings.” Emerson and Holmes employed language that was hard-hitting but open to revision; they generated organic vocabularies and syntaxes—Emerson about literary modernism, Holmes about law—that owed their intelligibility to a past from which they were breaking, albeit gradually. Holmes, acknowledging the transitional function of law and suggesting the contingency (though not the lack) of truth, once wrote, “Our test of truth is a reference to either a present or an imagined future majority in favor of our view.” This statement condenses Holmes’s poetics of transition or transformation into one maxim about truth, which is connected to law in Holmes’s metaphysics. As William James wrote about truth, so Holmes wrote about law; truth and law as ontological categories are similar in their want of signification and their mediate register in the human mind. The suggestion by Holmes here is that law—what it is and how it works—depends upon the transmutation and differential reproduction of ideas across time and space; law is not immanently knowable by humans, including and especially judges.
In 1859, Holmes wrote the class poem for his sophomore banquet. He wrote often of paintings and books. At none other than Emerson’s behest, Holmes studied Plato. Holmes even published a piece on Plato in the University Quarterly during his senior year, the same year his peers elected him Class Poet. (Holmes “rejected Platonism in metaphysics,” but he “accepted it in aesthetics.”) As Class Poet, Homes delivered a poetry reading to his graduating class; the reading was well-received.
During the Civil War, as a soldier of various ranks in various regiments, Holmes wrote poetry. Few of Holmes’s war letters survive because later in life Holmes burned nearly all of them; among the surviving, however, is one in which Holmes penned the following sonnet:
Lost and long-wandering at last I brake
From a deep forest’s sullen-opening jaws,
Where hungry junipers stretched bony claws
Like traps of devils, baited with a snake—
And all around the dark rocks seemed to take
Forbidden shapes of things that man outlaws,
Speckled like toads, and patched with all the flaws
Of stormy days, and lichen-ringed, and black—
Then wearied out—“Is there no hope?” I cried—
Hearken—A soft melodious rapture thrills
As from the forest’s deepest heart replied
Their hermit—and the music multiplied
And rose reechoing upward far and wide
From the dark valleys to the sunlet hills—
Other poems, including sonnets, have survived, as did some of Holmes’s pencil drawings, but none of these, perhaps, is so remembered as the sonnet he published in the Boston Evening Transcript in the fall of 1864:
Twentieth Massachusetts Volunteers
He steered unquestioning nor turning back,
Into the darkness and the unknown sea;
He vanished in the starless night, and we
Saw but the shining of his luminous wake.
Though sawest light, but ah, our sky seemed black,
And all too hard the inscrutable decree.
Yet, noble heart, full soon we follow thee,
Lit by the deeds that flamed along thy track.
Nay, art though hid in darkness, shall we say,
Or rather whisper with untrembling lips;
We see thee not, yet trust thou art not far,
But passing onward from this life’s eclipse
Hast vanished only as the morning star,
Into the glory of the perfect day.
This sonnet commemorates the death of Holmes’s friend Henry Abbot, a fellow soldier killed while leading a regiment on behalf of a wounded officer, himself incapable of leading. Small wonder, in light of these striking verses, that Thomas Hughes, the British writer, referred to Holmes in 1865 as both a “poet” and an “artist.”
Holmes did not instantly take to law. He could not decide whether to undertake a literary career, and his performance in law school was, like the performances of several notable American legal legends, unimpressive. Dr. Holmes, Wendell’s poet-father, probably approved of his son’s decision to attend law school because literature would, after all, always be there—and without professional and educational barriers to entry. (Holmes Senior knew this all too well, he being a medical doctor with a penchant for verse, and he being friends with such literary lawyers as James Russell Lowell and Henry Wadsworth Longfellow.)
At some point after returning home from war, Holmes befriended William James. By 1865, the year James sailed to Brazil with Louis Agassiz, James said that Holmes was “the only fellow here I care anything about.” Holmes probably did not reciprocate the feeling, even if he admired and acknowledged James’s unique intellect; the two men, at any rate, were not always on good terms, since they courted the same woman, Fanny Bowditch Dixwell. The tall and debonair Holmes won out and married Fanny in 1866. Around that time, Holmes cultivated a studious friendship with Henry James, with whom Holmes spent the summer of 1865 reading poetry and literature, including works by Robert Browning and Matthew Arnold.
Increasingly Holmes began to see in the law a way to merge his literary enthusiasm with his philosophical aptitude. In a letter to Emerson in 1876, Holmes wrote that “the law opens a way to philosophy as well as anything else, if pursued far enough, and I hope to prove it before I die.” Prove it he did. From this moment on, Holmes abandoned the writing of verse and devoted his time and energy to law and philosophy. It may be more accurate to say that Holmes blended verse with law and philosophy; for his jurisprudence is marked by turns of phrase, rhythm, rhyme, alliteration, allusion, assonance, and other literary devices. His jurisprudence is, in a word, poetry—and more memorable for being so.
 Mark DeWolfe Howe, Justice Oliver Wendell Holmes: The Shaping Years, 1841-1870 (Cambridge, Massachusetts: The Belknap Press of Harvard University Press, 1957) at 10.
 Ibid. at 11.
 Louis Menand, The Metaphysical Club (New York: Farrar, Straus and Giroux, 2001) at 25.
 Howe at 17.
 Ibid. at 34.
 Ibid. at 54.
 Ibid. at 43.
 Oliver Wendell Holmes Jr. to Patrick Augustine Sheehan, in Holmes-Sheehan Correspondence: Letters of Justice Oliver Wendell Holmes, Jr. and Canon Patrick Augustine Sheehan (David H. Burton, editor) (Fordham University Press, 1993) at 58, 60.
 Oliver Wendell Holmes Jr. to Elmer Gertz, March 1, 1899, quoted in Liva Baker, The Justice from Beacon Hill: The Life and Times of Oliver Wendell Holmes (New York: Harper Collins, 1991) at 172-73.
 Menand at 22.
 Howe at 47.
 Menand at 23.
 See Emerson, “Circles.”
 Jonathan Levin, The Poetics of Transition: Emerson, Pragmatism, and American Literary Modernism (Durham, N.C.: Duke University Press, 1999) at x.
 Ibid. at 14.
 Ibid. at x.
 Oliver Wendell Holmes Jr. “Natural Law.” 32 Harvard L. Rev. 40, 41 (1918).
 Howe at 50.
 Ibid. at 54.
 Ibid. at. 74-75.
 Ibid. at 56.
 Ibid. at 89.
 Ibid. at 165.
 Ibid. at 176.
 Ibid. at 201.
 Ibid. at 203.
 Ibid. at 204.