While still a clerk for Brandeis, Friendly received an offer to be an
associate professor at Harvard Law School, which the justice pressed him to accept, as he often wished for his clerks to enter academia or public life. Between a choice to assume the professorship or enter
private practice, Friendly chose the latter, becoming an associate in the prominent
white-shoe law firm of Root, Clark, Buckner, Howland & Ballantine (later
Dewey Ballantine) in September 1928. He was willing to sacrifice pay for a career in history, though did not share the same enthusiasm for legal scholarship and declined to be a professor. He had also explored the possibility of joining the Interstate Commerce Commission but became determined to work privately in New York. A practice in law offered independence and financial stability, qualities for which he yearned. (
pictured) served as a mentor to Friendly during both his undergraduate and graduate years, arranging for him positions at Harvard Law School.
Elitism and
antisemitism had been pervasive in law firms. His record at Harvard Law School made him a natural candidate for any New York firm, but antisemitism undermined Friendly's choices. Root, Clark was among the few firms in
Wall Street to hire Jews in addition to having a Jewish
partner, a characteristic which attracted him: "it was the only place in New York that a Jew could get a job." He interviewed also at
Sullivan & Cromwell, which also permitted Jews, though turned down an offer after undergoing a series of interviews, suspecting them to be predicated on antisemitic beliefs and the offer due only to his having been president of the
Harvard Law Review. For 31 years, Friendly stayed in private practice, where his specialty evolved into a combination of administrative,
common-carrier, and appellate law. After passing the New York bar in 1928, he developed an outstanding reputation during his years as an attorney from 1928 to 1959. He had begun in September 1928 at Root, Clark, where he eventually was made a partner on January 2, 1937. The firm first assigned him as an assistant to
Grenville Clark, a senior partner who had suffered a
nervous breakdown, with the intent that Friendly's aid and experience might reinvigorate him. Clark had been a prominent
corporate lawyer, a fellow graduate of Harvard Law School, and nominee of the
Nobel Peace Prize. Friendly's assistance, however, failed to improve his health. After months of uneventful work under Clark,
Elihu Root Jr. reassigned Friendly to a case representing
Pan American-Grace Airways and its president,
Juan Trippe. Friendly would assume control of the company's legal affairs with Root's consent not long afterward, primarily tasked with handling its contracts and diplomatic relationships. In 1929, he began a romantic relationship with Sophie Stern, daughter of future Judge
Horace Stern, and the couple married on September 4, 1930. It was his first serious relationship with a woman. In 1931, Brandeis once again urged Friendly to join the faculty of Harvard Law School, this time with the additional support of Frankfurter,
Roscoe Pound,
Calvert Magruder, and Edward Morgan. When Friendly refused in order to remain in private practice, Brandeis and Frankfurter attempted to get him to join the
Reconstruction Finance Corporation (RFC) as its
assistant general counsel the next year at the invitation of
Eugene Meyer. He turned down this office also, a decision which came as a disappointment to Frankfurter. The Law School continued to make repeated requests for Friendly to join its faculty, all of which were ultimately unsuccessful. From 1931 until 1933,
John Marshall Harlan II, a senior associate at Root, Clark, was embroiled with a case representing the
will of the late heirless Ella Virginia von Echtzel Wendel. Wendel, a wealthy recluse who was the sole owner of about $100 million of real estate, left a substantial fortune of $40–50 million to unknown
next of kin. Hundreds of claimants—many fraudulent—arose to inherit a part of the estate. Friendly was a prime assistant to Harlan, proving false the claim of a prominent candidate, and whose extensive research into the claimant's forgeries led to the dissolve of several other parties' cases. He would recall of the case: John Harlan and I often remarked to each other that the
Wendel Estate litigation was the most enjoyable forensic experience of our lives. It combined the elements of drama with—what is not always available—the financial resources needed to do a thoroughly professional job.
Pan Am and Cleary, Gottlieb Friendly was responsible for
Pan Am's congressional affairs, spending much of his time in Washington, D.C., litigating contracts. He accompanied Trippe in his role as a legal advisor and sat adjacent to him in conference meetings. During
World War II, Pan Am underwent rapid expansion, some of which were facilitated by Congressional funds appropriated in an agreement to use the company's airfields as a
staging ground for the war effort. Friendly and Pan Am lawyer
John Cobb Cooper sought to gain an advantage over the
U.S. Department of War in dictating its terms—their effective efforts later came under scrutiny in a Senate investigation led by Missouri Senator
Harry S. Truman, one which ultimately found no wrongdoing. With fellow associate
Leo Gottlieb, Friendly began considering leaving Root, Clark to start a new firm. The two left in 1945, forming Cleary, Gottlieb, Friendly & Cox (now
Cleary Gottlieb Steen & Hamilton), and were joined by a number of the firm's associates and partners. The departure of a substantial portion of its lawyers caused a serious split in Root, Clark; though the firm was damaged, it left on good terms with the newly formed Cleary, Gottlieb. Cleary, Gottlieb's immediate success dispelled Friendly's initial financial fears amidst a declining
postwar economy. Friendly brought Pan Am and
New York Telephone to the new firm. In 1946, the former appointed Friendly as its
general counsel and vice president, a position he would serve in until 1959. In working for both Cleary, Gottlieb and Pan Am simultaneously, he was split between commuting to the firm in Wall Street and the Pan Am headquarters located in the
Chrysler Building. Cleary, Gottlieb grew quickly, and it would attract high-profile clients such as
Bing Crosby,
Albert Einstein, the French government, and
Sherman Fairchild.
George W. Ball, who had joined the firm at its invitation, left to serve as
United States Under Secretary of State and, later,
United States Ambassador to the United Nations. Elihu Root Jr. and Grenville Clark, formerly of Dewey, Ballantine, resigned their positions to join Cleary, Gottlieb as
of counsel. While working for Pan Am, Friendly proved himself to be a skilled litigator, adept in
cross-examination. In a case involving the company,
Trans World Airlines (TWA), and
American Overseas Airlines (AOA), Friendly's cross-examination of multiple airline executives revealed contradictory statements which were refuted by internal data. On one occasion, his employment of a sometimes aggressive, unapologetic approach in questioning led to an objection by
counsel, though Friendly refused to recant his methods. The case, which concerned Pan Am's acquisition of the AOA, also involved
James M. Landis, former
Dean of Harvard Law School, who had a personal feud with both Friendly and Trippe; Landis represented the TWA in its efforts to compete against Pan Am for the purchase of the AOA. Friendly's cross-examination of Landis led to the upholding of Pan Am's acquisition by the
Civil Aeronautics Board, and President Harry Truman's signed approval on July 10, 1950, unexpectedly gave Pan Am the benefit of additional access to airways which it did not ask for. TWA appealed the controversial decision by Truman to the
United States Court of Appeals for the Second Circuit, which in turn upheld Friendly's arguments and struck down the appeal. The majority of Friendly's appellate litigation would be in the service of Pan Am, though in 1956 he won a
New York Court of Appeals case for the New York Telephone Company against the Public Service Commission. He also successfully distinguished himself in
oral argument at the
Court of Appeals for the First Circuit, where he argued before Judge Calvert Magruder, who had previously been among those to recommend Friendly to join the Harvard Law faculty. In 1959, Trippe approached Friendly to strike a contract with
Howard Hughes for the purchase of six
Boeing jets. With Raymond Cook, Hughes' lawyer, Friendly's efforts to clear the contract ensured its survival amidst a bond issue with the
U.S. Securities and Exchange Commission. The $40 million deal was one of the hastiest Friendly drafted and would be one of his last acts in private practice. == Nomination to the Second Circuit ==