Samuel Hand was an appellate Lawyer, who had risen rapidly through the ranks of an Albany-based law firm in the 1860s and, by age 32, was the firm's leading Lawyer. In 1878, he became the leader of the appellate bar and argued cases before the New York Court of Appeals in "greater number and importance than those argued by any other Lawyer in New York during the same period". Samuel Hand was a distant, intimidating figure to his son; Learned Hand later described his relations with his father as "not really intimate". Samuel Hand died from cancer when Learned was 14. Learned's mother thereafter promoted an idealized memory of her husband's professional success, intellectual abilities, and parental perfection, placing considerable pressure on her son.

Billings Learned Hand was born on January 27, 1872, in Albany, New York, the second and last child of Samuel Hand (1833–86) and Lydia Hand (née Learned). His mother's family traditionally used Surnames as given names; and Hand was named for a maternal uncle and a grandfather, both named Billings Peck Learned. The Hands were a prominent family with a tradition of activism in the Democratic Party. Hand grew up in comfortable circumstances on Albany's main residential street. The family had an "almost hereditary" attachment to the legal profession and has been described as "the most distinguished legal family in northern New York".

Hand started at Harvard College in 1889, initially focusing on classical studies and mathematics as advised by his late father. At the end of his sophomore year, however, he changed direction. He embarked on courses in philosophy and economics, studying under the eminent and inspirational Philosophers william James, Josiah Royce and George Santayana.

During the 1890s, Harvard Law School was pioneering the casebook method of teaching introduced by Dean Christopher Langdell. Apart from Langdell, Hand's professors included Samuel Williston, John Chipman Gray, and James Barr Ames. Hand preferred those teachers who valued Common sense and fairness, and ventured beyond casebook study into the philosophy of law. His favorite professor was James Bradley Thayer, who taught him evidence in his second year and constitutional law in his third. A man of broad interests, Thayer became a major influence on Hand's jurisprudence. He emphasized the law's historical and human dimensions rather than its certainties and extremes. He stressed the need for courts to exercise judicial restraint in deciding social issues.

At first, Hand found Harvard a difficult social environment. He was not selected for any of the social clubs that dominated campus life, and he felt this exclusion keenly. He was equally unsuccessful with the Glee Club and the football team; for a time he rowed as a substitute for the rowing club. He later described himself as a "serious boy", a hard worker who did not smoke, drink, or consort with prostitutes. He mixed more in his sophomore and senior years. He became a member of the Hasty Pudding Club and appeared as a blond-wigged chorus girl in the 1892 student musical. He was also elected President of The Harvard Advocate, a student literary magazine.

Hand's studious ways resulted in his election to Phi Beta Kappa, an elite society of scholarly students. He graduated with highest honors, was awarded a master's as well as a bachelor's degree, and was chosen by his classmates to deliver the Class Day oration at the 1893 commencement. Family tradition and expectation suggested that he would study law after graduation. For a while, he seriously considered post-graduate work in philosophy, but he received no encouragement from his family or philosophy professors. Doubting himself, he "drifted" toward law.

Hand's three years at Harvard Law School were intellectually and socially stimulating. In his second year, he moved into a boarding house with a group of fellow law students who were to become close friends. They studied hard and enjoyed discussing philosophy and literature and telling bawdy tales. Hand's learned reputation proved less of a hindrance at law school than it had as an undergraduate. He was elected to the Pow-Wow Club, in which law students practiced their skills in moot courts. He was also chosen as an Editor of the Harvard Law Review, although he resigned in 1894 because it took too much time from his studies.

Hand graduated from Harvard Law School in 1896 at the age of 24. He returned to Albany to live with his mother and aunt, and started work for the law firm in which an uncle, Matthew Hale, was a partner. Hale's unexpected death a few months later obliged Hand to move to a new firm, but by 1899, he had become a partner. He had difficulty attracting his own clients, however, and found the work trivial and dull. Much of his time was spent researching and writing briefs, with few opportunities for the appellate work he preferred. His early courtroom appearances, when they came, were frequently difficult, sapping his fragile self-confidence. He began to fear that he lacked the ability to think on his feet in court.

Hand's skepticism extended to his political philosophy: he once described himself as "a conservative among liberals, and a liberal among conservatives". As early as 1898, he rejected his family's Jeffersonian Democratic tradition. His thoughts on liberty, collected in The Spirit of Liberty (1952), began by recalling the political philosophies of Thomas Jefferson and Alexander Hamilton. Jefferson believed that each individual has a right to freedom, and that government, though necessary, threatens that freedom. In contrast, Hamilton argued that freedom depends on government: too much freedom leads to anarchy and the tyranny of the mob. Hand, who believed, following Thomas Hobbes, that the rule of law is the only alternative to the rule of brutality, leaned towards Hamilton. Since the freedom granted to the American pioneers was no longer feasible, he accepted that individual liberty should be moderated by society's norms. He nevertheless saw the liberty to create and to choose as vital to peoples' humanity and entitled to legal protection. He assumed the goal of human beings to be the "good life", defined as each individual chooses.

For two years, Hand tried to succeed as a Lawyer by force of will, giving all his time to the practice. By 1900, he was deeply dissatisfied with his progress. For intellectual stimulation, he increasingly looked outside his daily work. He wrote scholarly articles, taught part-time at Albany Law School, and joined a lawyers' discussion group in New York City. He also developed an interest in politics.

After reaching the age of 30 without developing a serious interest in a woman, Hand thought he was destined for bachelorhood. But, during a 1901 summer holiday in the Québec resort of La Malbaie, he met 25-year-old Frances Fincke, a graduate of Bryn Mawr College. Though indecisive in most matters, he waited only a few weeks before proposing. The more cautious Fincke postponed her answer for almost a year, while Hand wrote to and occasionally saw her. He also began to look more seriously for work in New York City. The next summer, both Hand and Fincke returned to La Malbaie, and at the end of August 1902, they became engaged and kissed for the first time. They married on December 6, 1902, shortly after Hand had accepted a post with the Manhattan law firm of Zabriskie, Burrill & Murray. The couple had three daughters: Mary Deshon (born 1905), Frances (born 1907), and Constance (born 1909). Hand proved an anxious husband and father. He corresponded regularly with his Doctor brother-in-law about initial difficulties in conceiving and about his children's illnesses. He survived pneumonia in February 1905, taking months to recover.

Hand continued to be disappointed in his progress at work. A move to the firm of Gould & Wilkie in January 1904 brought neither the challenges nor the financial rewards for which he had hoped. "I was never any good as a Lawyer," he later admitted. "I didn't have any success, any at all." In 1907, deciding that at the age of 35 success as a Wall Street Lawyer was out of reach, he lobbied for a potential new federal judgeship in the United States District Court for the Southern District of New York, the federal court headquartered in Manhattan. He became involved briefly in local Republican politics to strengthen his political base. In the event, Congress did not create the new judgeship in 1907; but, when the post was finally created in 1909, Hand renewed his candidacy. With the help of the influential Charles C. Burlingham, a senior New York Lawyer and close friend, he gained the backing of Attorney General George W. Wickersham, who urged President william Howard Taft to appoint Hand. One of the youngest federal judges ever appointed, Hand took his judicial oath at age 37 in April 1909.

Hand has been called one of the United States' most significant judicial Philosophers. A leading advocate of judicial restraint, he took seriously Alexander Hamilton's formulation that "the judiciary ... may truly be said to have neither force nor will, but merely judgement." Any judicial ruling that had the effect of legislating from the bench troubled Hand. In 1908, in his article "Due Process of Law and the Eight-Hour Day", he attacked the 1905 Supreme Court ruling in Lochner v. New York, which had struck down a law prohibiting bakery staff from working more than ten hours a day. The Supreme Court went on to strike down a series of similar worker-protective laws on the grounds that they restricted freedom of contract. Hand regarded this principle as undemocratic. "For the state to intervene", he argued, "to make more just and equal the relative strategic advantages of the two parties to the contract, of whom one is under the pressure of absolute want, while the other is not, is as proper a legislative function as that it should neutralize the relative advantages arising from fraudulent cunning or from superior force."

Learned Hand played a key role in the interpretation of new federal crime laws in the period following the passing of the U.S. Criminal Code in 1909. In a series of judicial opinions and speeches, he opposed excessive concern for Criminal defendants, and wrote "Our dangers do not lie in too little tenderness to the accused. Our procedure has always been haunted by the ghost of the innocent man convicted. ... What we need to fear is the archaic formalism and watery sentiment that obstructs, delays and defeats the prosecution of crime." He insisted that harmless trial errors should not automatically lead to a Reversal on appeal. Hand balanced these views with important decisions to protect a defendant's constitutional rights concerning unreasonable searches, forced confessions and cumulative sentences.

Between 1910 and 1916, Hand tried to translate his political philosophy into political action. Having read Croly's The Promise of American Life and its anti-Jeffersonian plea for government intervention in economic and social issues, he joined the Progressive Party. However, he discovered that party politicking was incompatible not only with his role as a judge but with his philosophical objectivity. The pragmatic philosophy Hand had imbibed from william James at Harvard required each issue to be individually judged on its merits, without partiality. In contrast, political action required partisanship and a choice between values. After 1916, Hand preferred to retreat from party politics into a detached skepticism. His belief in central planning resurfaced during the 1930s in his growing approval of Franklin D. Roosevelt's New Deal, as he once again—though this time as an observer—endorsed a program of government intervention. Hand was also an interventionist on foreign policy, supporting U.S. involvement in both world wars, and disdained isolationism.

Following his appointment as a judge, Hand became politically active in the cause of New Nationalism. With reservations, in 1911 he supported Theodore Roosevelt's return to national politics. He approved of the former president's plans to legislate on behalf of the underprivileged and to control corporations, as well as of his campaign against the abuse of judicial power. Hand sought to influence Roosevelt's views on these subjects, both in person and in print, and wrote articles for Roosevelt's magazine, The Outlook. His hopes of swaying Roosevelt were often dashed. Roosevelt's poor grasp of legal issues particularly exasperated Hand.

Despite overwhelming support for Roosevelt in the primaries and polls, the Republicans renominated the incumbent President Taft. A furious Roosevelt bolted from the party to form the Progressive Party, nicknamed the "Bull Moose" movement. Most Republican progressives followed him, including Hand. The splitting of the Republican vote, however, harmed both Roosevelt's and Taft's chances of winning the November 1912 presidential election. As Hand expected, Roosevelt lost to the Democratic Party's Woodrow Wilson, though he polled more votes than Taft.

Hand took the defeat in his stride. He considered the election merely as a first step in a reform campaign for "real national democracy". Though he had limited his public involvement in the election campaign, he now took part in planning a party structure. He also accepted the Progressive nomination for chief judge of New York Court of Appeals, then an elective position, in September 1913. He refused to campaign, however, and later admitted that "the thought of harassing the electorate was more than I could bear". His vow of silence affected his showing, and he received only 13% of the votes. Hand came to regret his candidacy: "I ought to have lain off, as I now view it; I was a judge and a judge has no Business to mess into such things."

By 1916, Hand realized that the Progressive Party had no Future, as the liberal policies of the Democratic government were making much of its program redundant. Roosevelt's decision not to stand in the 1916 presidential election dealt the party its death blow. Hand had already turned to an alternative political outlet in Herbert Croly's The New Republic, a liberal magazine which he had helped launch in 1914. Hand wrote a series of unsigned articles for the magazine on issues of social reform and judicial power; his only signed article was "The Hope of the Minimum Wage", published in November 1916, which called for laws to protect the underprivileged. Often attending staff dinners and meetings, Hand became a close friend of the gifted young Editor Walter Lippmann. The outbreak of war in Europe in 1914 had coincided with the founding of the magazine, whose pages often debated the events in Europe. The New Republic adopted a cautiously sympathetic stance towards the Allies, which Hand supported wholeheartedly. After the United States entered the war in 1917, Hand considered leaving the bench to assist the war effort. Several possible war-related positions were suggested to him. Nothing came of them, aside from his chairing a committee on intellectual property law that suggested treaty amendments for the Paris Peace Conference.

Learned Hand wrote approximately four thousand judicial opinions during his career. Admired for their clarity and analytic precision, they have been quoted more often in Supreme Court opinions and by legal scholars than those of any other lower-court judge. Both Hand's dissent in United States v. Kennerley and his ruling in United States v. Levine have often been cited in obscenity cases. Hand's view that literary works should be judged as a whole and in relation to their intended readership is now accepted in American law. His use of historical data to gauge legislative intent has become a widespread practice. According to Archibald Cox: "The opinions of Judge Hand have had significant influence both in breaking down the restrictions imposed by the dry literalism of conservative tradition and in showing how to use with sympathetic understanding the information afforded by the legislative and administrative processes." Hand's decision in the 1917 Masses case influenced Zechariah Chafee's widely read book, Freedom of Speech (1920). In his dedication, Chafee wrote, "[Hand] during the turmoil of war courageously maintained the traditions of English-speaking freedom and gave it new clearness and strength for the wiser years to come."

After the demise of the Progressive Party, Hand had withdrawn from party politics. He committed himself to public impartiality, despite his strong views on political issues. He remained, however, a strong supporter of freedom of speech, and any sign of the "merry sport of Red-baiting" troubled him. In 1920, for Example, he wrote in support of New York Governor Al Smith's veto of the anti-sedition Lusk Bills. The New York Assembly had approved these bills in a move to bar five elected Socialist Party legislators from taking their seats. In 1922, Hand privately objected to a proposed limit on the number of Jewish students admitted to Harvard College. "If we are to have in this country racial divisions like those in Europe," he wrote, "let us close up shop now".

The next Second Circuit vacancy arose in 1921, but with the conservative Warren G. Harding administration in power, Hand did not put himself forward. Nonetheless Hand's reputation was such that by 1923, Supreme Court Justice Oliver Wendell Holmes, Jr. wanted him on the Supreme Court, and in 1924 Harding's successor, Calvin Coolidge, appointed Hand to the Second Circuit. It was a sign of Hand's increased stature that figures such as Coolidge and Chief Justice william Howard Taft now endorsed him. Coolidge sought to add new blood to a senior judiciary that was seen as corrupt and inefficient. In 1926 and 1927, the Second Circuit was strengthened by the appointments of Thomas Walter Swan and Hand's cousin Augustus Noble Hand.

Hand had voted for Hoover in 1928, and he did so again in 1932; but in 1936, he voted for the Democrats and Franklin D. Roosevelt, as a reaction to the economic and social turmoil that followed the Wall Street Crash of 1929. With the Great Depression setting in, Hand favored a policy of interventionist central government. He came to accept Frankfurter's view that redistribution of wealth was essential for economic recovery. Hoover resisted this approach, favoring individualism and free enterprise. Roosevelt, on the other hand, promised the voters a New Deal. They elected him on a platform of strong executive leadership and radical economic reform. Hand voted for Roosevelt again in 1940 and 1944, but he remained vigilant on the constitutional dangers of big government. Like others, including Walter Lippmann, he sensed the dictatorial potential of New Deal policies. He had no hesitation in condemning Roosevelt's 1937 bill to expand the Supreme Court and pack it with New Dealers.

In public, Hand discussed issues of democracy, free speech, and toleration only in general terms. This discretion, plus a series of impressive speaking engagements, won him the respect of legal scholars and journalists, and by 1930 he was viewed as a serious candidate for a seat on the Supreme Court. His friend Felix Frankfurter, then a Harvard Law School professor, was among those lobbying hard for Hand's appointment. President Herbert Hoover chose to bypass him, possibly for political reasons, and appointed Charles Evans Hughes, who had previously served on the Court for six years before resigning to become the Republican candidate for President in 1916, as Chief Justice. With Hughes and another New Yorker, Harlan Fiske Stone, on the Court, the promotion of a third New Yorker was then seen as impossible.

Hand became an acknowledged expert on New Deal statutes. He relished the challenge of interpreting such legislation, calling it "an act of creative imagination". In a 1933 broadcast, he explained the balancing act required of a judge in interpreting statutes:

Hand was increasingly called upon to judge cases arising from the flood of New Deal legislation. The line between central government authority and local legislation particularly tested his powers of judgment. In 1935, the case of United States v. Schechter came before the Second Circuit. Hand and his two colleagues had to judge whether a New York poultry firm had contravened New Deal legislation on unfair trade practices. They ruled that the National Industrial Recovery Act did not apply to the Schechter Poultry Corporation, which traded solely within the state. "The line is no doubt in the end arbitrary," Hand wrote in a memorandum, "but we have got to draw it, because without it Congress can take over all the government." The Supreme Court later affirmed Hand's decision.

The issue concerned Hand again during the New Deal period, when the Supreme Court repeatedly overturned or blocked Franklin D. Roosevelt's legislation. As an instinctive democrat, Hand was appalled that an elected government should have its laws struck down in this way. He viewed it as a judicial "usurpation" for the Supreme Court to assume the role of a third chamber in these cases. As far as he was concerned, the Constitution already provided a full set of checks and balances on legislation. Nevertheless, Hand did not hesitate to condemn Roosevelt's frustrated attempt to pack the Supreme Court in 1937, which led commentators to warn of totalitarianism. The answer, for Hand, lay in the separation of powers: courts should be independent and act on the legislation of elected governments.

When war broke out in Europe in 1939, Learned Hand adopted an anti-isolationist stance. He rarely spoke out publicly, not only because of his position but because he thought bellicosity unseemly in an old man. In February 1939, he became his court's senior circuit leader (in effect, chief judge, although the title was not created until 1948). In this post, Hand succeeded Martin Manton, who had resigned after corruption allegations that later led to Manton's Criminal conviction for bribery. Not an admirer of Manton, Hand nonetheless testified at his trial that he had never noticed any corrupt behavior in his predecessor. Having sat in two cases in which Manton accepted bribes, Hand worried for years afterward that he should have detected his colleague's corruption.

Hand was relieved when the United States entered the war in December 1941. He felt free to participate in organizations and initiatives connected with the war effort, and was particularly committed to programs in support of Greece and Russia. He backed Roosevelt for the 1944 election, partly because he feared a return to isolationism and the prolonging of the wartime erosion of civil liberties. In 1943, the House Un-American Activities Committee or "Dies Committee", for Example, had aroused his fears with an investigation into "subversive activities" by government workers. Hand's contemporary at Harvard College, Robert Morss Lovett, was one of those accused, and Hand spoke out on his behalf. As the end of the war approached, there was much talk of international peace organizations and courts to prevent Future conflict, but Hand was skeptical. He also condemned the Nuremberg war-crimes trials, which he saw as motivated by vengeance; he did not believe that "aggressive war" could be construed as a crime. "The difference between vengeance and justice," he wrote later, "is that justice must apply to all."

In 1942, Hand's friends once again lobbied for him to fill a Supreme Court vacancy, but Roosevelt did not appoint him. The President gave age as the reason, but philosophical differences with Hand may also have played a part. Another explanation lies in one of Justice william O. Douglas's autobiographies, where Douglas states that, despite Roosevelt's belief that Hand was the best person for the job, Roosevelt had been offended by the pressure Justice Felix Frankfurter placed on the President during a vigorous letter-writing campaign on Hand's behalf. D.C. Circuit Judge Wiley Blount Rutledge, whom Roosevelt appointed, died in 1949, while Hand lived until 1961. In a February 1944 correspondence with Frankfurter, Hand expressed a low opinion of Roosevelt’s new appointees, referring to Justice Hugo Black, Justice Douglas, and Justice Frank Murphy as "Hillbilly Hugo, Good Old Bill, and Jesus lover of my Soul". Deeply disappointed at the time, Hand later regretted his ambition: "It was the importance, the power, the trappings of the God damn thing that really drew me on."

Louis Dow had died in 1944, with Frances Hand at his side. The Hands' marriage then entered its final, happiest phase, in which they rediscovered their first love. Former law clerks have provided intimate details of Hand's character during the last decade of his life. Legal Philosopher Ronald Dworkin recalls that Hand, scrupulous about public economy, used to turn out the Lights in all the offices at the end of each day. For the same reason, he refused Dworkin the customary month's paid vacation at the end of his Service. Shortly afterward, to Dworkin's surprise, Hand wrote him a personal check for an extra month's pay as a wedding present. Hand was known for his explosive temper. Gunther remembers him throwing a paperweight in his direction which narrowly missed. Hand had a habit of turning his seat 180° on lawyers whose arguments annoyed him, and he could be bitingly sarcastic. In a typical memo, he wrote, "This is the most miserable of cases, but we must dispose of it as though it had been presented by actual lawyers." Despite such outbursts, Hand was deeply insecure throughout his life, as he fully recognized. In his 80s, he still fretted about his rejection by the elite social clubs at Harvard College. He was convinced that his wife had rescued him from a life as a "melancholic, a failure [because] I should have thought myself so, and probably single and hopelessly hypochondriac".

After Hand's lectures and publications became widely known, his influence reached courts throughout the country. On the occasion of his 75th birthday on January 27, 1947, The Washington Post reported: "He has won recognition as a judges' judge. His opinions command respect wherever our law extends, not because of his standing in the judicial hierarchy, but because of the clarity of thought and the cogency of reasoning that shape them."

In the case of United States v. Dennis in 1950, Hand made a ruling that appeared to contradict his Masses decision. By then, a series of precedents had intervened, often based on Oliver Wendell Holmes's "clear and present danger" test, leaving him less room for maneuver. Hand felt he had "no choice" but to agree that threats against the government by a group of Communists were illegal under the repressive Smith Act of 1940. In order to do so, he interpreted the "clear and present danger" in a new way. "In each case," he wrote, "[courts] must ask whether the gravity of the 'evil', discounted by its improbability, justifies such invasion of free speech as is necessary to avoid the danger." This formula allowed more scope for curbing free speech in cases where, as the government believed with Communism, the danger was grave, whether it was immediate or not. Critics and disappointed liberals accused Hand of placing his concern for judicial restraint ahead of freedom of speech. Hand confided to a friend that, if it had been up to him, he would "never have prosecuted those birds".

To the wider public, who knew little of his legal work, Hand was by then a folk hero. Social scientist Marvin Schick has pointed out that this mythic status is a paradox. Because Hand never served on the Supreme Court, the majority of his cases were routine and his judgments rooted in precedent. On Hand's retirement in 1951, Felix Frankfurter predicted that his "actual decisions will be all deader than the Dodo before long, as at least many of them are already". Working for a lower court, however, saved Hand from the taint of political influence that often hung over the Supreme Court. Hand's eloquence as a Writer played a larger part in the spread of his influence than the substance of his decisions; and Schick believes that the Hand myth brushes over contradictions in his legal philosophy. Hand's reputation as a libertarian obscures the fact that he was cautious as a judge. Though a liberal, he argued for judicial restraint in interpreting the Constitution, and regarded the advancement of civil liberties as a task for the legislature, not the courts. In his 1958 Holmes Lectures, for Example, he voiced doubts about the constitutionality of the Warren Court's civil rights rulings. This philosophy of judicial restraint failed to influence the decisions of the Supreme Court during Hand's lifetime and afterwards.

Hand followed this up with an address to the Board of Regents of the University of the State of New York the next year. Once again, his attack on McCarthyism won approval from many liberals. Asked to send a copy of his views to McCarthy, Hand replied that he had Richard Nixon in mind as well. Despite his concerns about Nixon as vice President, Hand voted for Dwight Eisenhower in the 1952 election, later crediting Eisenhower with bringing about McCarthy's downfall in 1954.

In 1953, Hand wrote a scathing dissent from a Second Circuit decision to affirm the perjury conviction of william Remington, a government Economist accused of Communist sympathies and activities. In 1951, the same panel had overturned Remington's previous conviction for perjury, but in the appeal of the later case Hand was outvoted two to one. The prosecution produced stronger evidence against Remington this time, much of it obtained from his wife. Sentenced to three years imprisonment, Remington was murdered in November 1954 by three fellow inmates, who beat him over the head with a brick wrapped in a sock. According to Hand's biographer Gunther, "The image of Remington being bludgeoned to death in prison haunted Hand for the rest of his life."

By 1958, Hand was suffering from intense pain in his back and faced difficulty in walking. "I can just manage, with not infrequent pauses, to walk about a third of a mile," he wrote to Felix Frankfurter. "My feet get very numb and my back painful. The truth is that 86 is too long." Soon, he was obliged to use crutches, but he remained mentally sharp and continued to hear cases. In 1960, he worked briefly on President Dwight Eisenhower's "Commission on National Goals", but he resigned because "it involved more work than in the present state of my health I care to add to the judicial work that I am still trying to do".

By June 1961, Hand was in a wheelchair. He joked that he felt idle because he had taken part in no more than about 25 cases that year, and that he would start another job if he could find one. The following month, he suffered a heart attack at Cornish. He was taken to St Luke's Hospital in New York City, where he died peacefully on August 18, 1961. The New York Times ran a front-page obituary. The Times of London wrote: "There are many who will feel that with the death of Learned Hand the golden age of the American judiciary has come to an end."

Finally, in an essay called Origin of a Hero discussing his novel the Rector of Justin, author Louis Auchincloss says the main character was not based on a headmaster; certainly not as was often speculated Groton's famous Endicott Peabody. "If you want to disguise a real life character," Auchincloss advised fellow novelists, "just change his profession." His actual model for the Rector of Justin was "the greatest man it has been my good luck to know" – Judge Learned Hand.

Hand spent two years at a small primary school before transferring at the age of seven to The Albany Academy, which he attended for the next 10 years. He never enjoyed the Academy's uninspired teaching or its narrow curriculum, which focused on Ancient Greek and Latin, with few courses in English, history, science, or modern languages. Socially, he considered himself an outsider, rarely enjoying recesses or the school's military drills. Vacations, spent in Elizabethtown, New York, were happier times. There, Hand developed a life-long friendship with his cousin and Future colleague Augustus Noble Hand, two years his senior. The two were self-confessed "wild boys", camping and hiking in the woods and hills, where Hand developed a love of nature and the countryside. Many years later, when he was in his 70s, Hand recorded several songs for the Library of Congress that he had learned as a boy from Civil War veterans in Elizabethtown. After his father's death, he felt more pressure from his mother to excel academically. He finished near the top of his class and was accepted into Harvard College. His classmates—who opted for schools such as Williams and Yale—thought it a "stuckup, snobbish school".