Cass R. Sunstein ’75

In the trivia game known as “Six Degrees of Kevin Bacon,” the object is to start with a random actor, link to one of that actor’s co-stars, and then—in only five more steps—get to the ubiquitous actor Kevin Bacon. In 2007, two Vanderbilt professors set out to find Bacon’s legal scholar analogue: someone famous who collaborates often in a variety of genres and who gives no sign of slowing down anytime soon.

The man they selected is today’s most frequently cited legal scholar in America, the author of over 500 works including more than 15 books, a constitutional law expert whose interests range from how public policy can improve one’s life to how the online coalescence of like-minded groups can stifle dialogue and undermine democracy. He is Cass R. Sunstein ’75, President Barack H. Obama’s nominee for the head of the White House Office of Information and Regulatory Affairs, informally known as the regulatory czar. Under the new administration, Sunstein will have the task of supervising regulations from health care to the environment.

From the moment that Sunstein entered the Middlesex School, a preparatory school in Concord, Mass., in eighth grade, he seemed destined to excel in all aspects of student life. By his senior year, he was co-editor of the student newspaper, The Anvil, editor-in-chief of the yearbook, and a national-caliber squash player, having learned to play while at the school.

Middlesex classmate Robert E. Harvey recalls that Sunstein “was working so much that he wasn’t hanging out with an awful lot of people all the time.” Sunstein’s closest friend at Middlesex, Craig B. McArdle ’75, recalls the day before their graduation, when he asked Sunstein to play squash with him. He said that while sitting at his typewriter in his magazine-strewn room, Sunstein refused, declaring, “too much play and too little work makes Cass a dull boy.”

According to McArdle, such occurrences were common, especially during Sunstein’s years as an upperclassman when he decided to focus on writing. “He had this weird thing where he’d be hunched over the typewriter kind of like Glenn Gould over the piano,” says McArdle. “He’d type with one finger on each hand, incredibly fast. He’d just be concentrating, so focused, it was like somebody watching TV. You’d have to say [his name] several times to get his attention.”

After graduating with Middlesex’s highest honors, Sunstein brought his intellectual curiosity and his Advanced Placement credits to Harvard in the fall of 1972, where he set out on an Advanced Standing track in English. A Currier resident, Sunstein belonged to the Hasty Pudding and the Lampoon, a semi-secret Sorrento Square social organization that used to occasionally publish a so-called humor magazine.

Kurt E. Andersen ’76, a novelist, political writer, and former ’Poon editor, remembers Sunstein as “a dry and funny writer,” with “a kind of rigor in his work not true of everybody then or now.” Despite Sunstein’s humor, the castle never quite became his natural home. “He always seemed to me slightly abashed at the entire Lampoon thing,” says Andersen about the teetotaling undergrad. “I had a sense that he didn’t quite know what he was getting into.”

One area of undergraduate life that Sunstein seemed not to struggle with was romance. According to McArdle, most Middlesex graduates entered college with a distinct uneasiness around the opposite sex, but Sunstein managed to overcome this with his natural charms. McArdle recalls that Sunstein was “in many ways...kind of a chick magnet because he had this very innocent look and was bright.”

It was not until his third and senior year at Harvard that he decided to enter law school instead of pursuing English graduate work, Sunstein said in a 2008 interview with Fifteen Minutes. “I thought that law would have more opportunities and that you could take a lot of different paths if you went into law,” he said.

Despite his busy schedule, Sunstein remained well-known and well-liked by his classmates. “He was a very, very hard worker,” says Hugh C. Fortmiller, Jr. ’56, Sunstein’s English teacher and senior year academic advisor, “but he also had time to be a friend and an amusing conversationalist ... but he had a hell of a lot of responsibilities.”

Upon graduation from Harvard Law School in 1978, Sunstein clerked for Thurgood Marshall and later became a professor at the University of Chicago Law School, where he befriended Obama. Last year he left the University of Chicago to return to Cambridge and took up a post advising Obama during his presidential campaign. David A. Schkade, a professor at the University of California, San Diego, says he marveled at Sunstein’s work ethic, having worked with him to study the unpredictability of punitive damages in legal cases. “We’d have a conversation on Thursday and by Saturday night there’d be a 15-page draft in an e-mail,” he said.

One thing that has remained constant in Sunstein’s life is his love of squash. In 2008, Sunstein said that he played three to four times per week. The sport gave him chances to learn the power of colorful analogy from legendary coach Jack Barnaby ’32, to predict other players’ moves, and, in Sunstein’s first year at HLS, to achieve national supremacy by upsetting what then-assistant-coach David R. Fish ’72 called a “juggernaut of a Princeton team.”

Despite his cross-disciplinary excellence, Sunstein seems to generate goodwill among his colleagues and even his competitors. Harvey amicably recalls coming in second to Sunstein in the election for yearbook editor at Middlesex. “I’m very amused by that,” Harvey says, “because I’m not the second-most cited law professor in the United States.”