Robert Maynard Hutchins was born in Brooklyn in 1899, the second of three sons of William James Hutchins, a Presbyterian minister and future Berea College president. Eight years later, the family moved to Oberlin, Ohio, site of Oberlin College, where William Hutchins became an instructor. Oberlin was a small community dedicated to evangelical ideals of righteousness and hard work, which had a lifelong influence on Hutchins. Hutchins studied at Oberlin Academy and subsequently Oberlin College from 1915 to 1917.  At age 18 in 1917, shortly after the United States entered World War I, Hutchins joined the ambulance service of the United States Army, together with his brother William. The Hutchins brothers served in an all-Oberlin unit, Section 587, which for much of the war was stationed at the Allentown Fair Grounds, where they were tasked with creating a barracks. Upon subsequent deployment to Italy, Hutchins was awarded the Croce di Guerra.  Returning from the war in 1919, Hutchins went to Yale University (B.A. 1921). At Yale he encountered a very different society from what he had known before at Oberlin; the tone was set by preparatory school graduates who defied Prohibition. However, Hutchins did not enjoy the same level of financial support, and in his junior and senior years, he worked menial jobs for up to six hours per day to cover living expenses. In his senior year, he was tapped for the Wolf's Head Society. Having already fulfilled his graduation requirements, he also enrolled in Yale Law School. Fascinated by the case method, Hutchins subsequently regarded this as the beginning of his true education. Shortly after his graduation in 1921, Hutchins married Maude Phelps McVeigh. They would have three daughters together, the first born in 1925.  After spending a year teaching high school History and English in Lake Placid, New York, he was hired to become the Secretary of the Yale Corporation. In this position he was the principal assistant to the president of Yale, with responsibility for alumni relations and fundraising. Returning to New Haven, he also resumed his studies at Yale Law School (LL.B 1925). Upon completing his LL.B., graduating at the top of his class, he was invited to join the Yale Law faculty, teaching courses on evidence and utility law. He became acting Dean of Yale Law School in 1927, and full Dean in 1928. It was at this point, when he was the Dean of Yale Law while still in his 20s, that Hutchins became a national figure.  At the time, Yale Law School was dominated by the Legal Realists and Hutchins sought to promote Legal Realism during his time as dean. Skeptical of the received rules of evidence that he had taught as a professor, he worked to integrate the findings of psychology, sociology and logic with the law. His supporters in this enterprise included William O. Douglas, who left Columbia School of Law to work under Hutchins at Yale. Hutchins played a key role in convincing the Rockefeller Foundation to fund an Institute of Human Relations at Yale, to foster partnerships between the social sciences and law and medicine.

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