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A recent visit to Washington, D.C., brought together the two seemingly incompatible worlds in which Kermit Roosevelt III, assistant professor of law, happily resides these days. During the day he rubbed elbows with Hollywood heavyweight Frank Langella and “Dawson’s Creek” star Joshua Jackson as they filmed a pilot based on Roosevelt’s book In the Shadow of the Law, a best-selling legal thriller that has just come out in paperback. Scenes based on the book, a penetrating look at K Street law firm life, were played out for the cameras at the Willard Hotel, along Pennsylvania Avenue, and on the Mall. But that evening, even as he sheepishly admitted how much fun his day had been, Roosevelt was clearly looking forward to the second half of his trip just as much. The next morning he would head to the Supreme Court to watch oral arguments in Woodford v. Ngo, a dense but important Prison Litigation Reform Act case in which he had filed an amicus curiae brief. He was anxious to see the argument and to catch a courtroom glimpse of Justice David Souter, for whom he clerked in 1999. “I would stop by his chambers to say hello, but I have to catch a train back to Philadelphia,” said Roosevelt, who teaches at the University of Pennsylvania. Roosevelt, the great-great-grandson of President Theodore Roosevelt, spoke modestly and matter-of-factly about both of his identities — Hollywood-bound author and Supreme Court-bound law professor — that evening, as if trying not to let either one overwhelm the other. Of the television pilot, he said, “I’m trying to be realistic” about its chances of being picked for the CBS fall lineup. Weeks later, it appeared that the legal side of his life was doing better than the Hollywood part. “The news on the television show is not great,” he reported. CBS had not put “Capitol Law,” as it is called, on the fall schedule, though it still had a chance to fill a prime-time slot at some point in the future. But the other part of the trip to Washington had been a more positive experience. The March 22 oral argument had gone well, though he would not predict victory. Roosevelt said he could swear Souter had smiled at him in the audience as he asked one of the advocates a question that came straight out of Roosevelt’s brief. (On June 22 the Supreme Court ruled 6-3 against Roosevelt’s viewpoint in Woodford v. Ngo. Souter and Justice Ruth Bader Ginsburg joined a dissent Justice John Paul Stevens wrote that cited Roosevelt’s brief.) Roosevelt’s brush with Hollywood, it appears, has not dulled the luster of his law-professor world. In his understated way, Roosevelt, 34, is reveling in both. Roosevelt wrote his thriller after trying to find a publisher for three more-literary novels, one of which he’d written as a student at Yale Law School. Those went nowhere, so without hesitation he switched genres. In the Shadow of the Law is clearly not Roosevelt’s attempt to sell out in order to write a best seller. It has literary touches and a less frantic, heart-pounding pace than most thrillers. It is a compelling, irresistible read nonetheless, full of devastating observations about life at the fictitious K Street law firm of Morgan Siler. With a depressing ring of accuracy, Roosevelt captures the bleak rhythms, the life cycle, the warp and the woof of legal jobs, from first-year associate to ruler-of-the-universe managing partner. Associates are worked to the nub and then discarded, their souls emptied and their enthusiasm drained. One, like Roosevelt, a former Supreme Court law clerk, comes to realize that his clerkship was like “dating a girl in college and thinking that all relationships are like that, and realizing only after it was over that you would never have it so good again.” This associate becomes obsessed with getting a new ergonomic desk chair. Informed that his old one won’t be replaced until it breaks, he tears it apart, limb by limb. He gets the new chair. In one memorable scene, managing partner Peter Morgan, standing at a men’s room urinal, asks another associate at the urinal next to his, “What are you thinking about?” The surprised associate blurts out, “Work.” Morgan replies, “I could tell. Make sure to bill it.”
Panic Gives Way to Resignation
An excerpt from In the Shadow of the Law by Kermit Roosevelt III, describing the day of a first-year associate at Morgan Siler, a fictitious K Street law firm. “Mark Clayton was at the customary point in his day when panic gave way to resignation. His office was small, smaller even than the norm for first-year associates, but a compensatory window offered a partially obstructed view of downtown Washington. Once this had seemed cause for optimism, as his sensible gray suits and framed diplomas had seemed confirmation of his place in the professional world. Both now struck him differently, the suits a poor camouflage, the diplomas almost a silent rebuke. . . . “Initially, he’d woken with a sense of excitement, the new job beckoning like the big football games of high school. Those had tended toward anticlimax, involving chiefly a period of waiting until the outcome was sufficiently removed from doubt for his name to be called. Now, likewise, he sat at his desk for long hours while the day’s excitement dulled; then, usually midafternoon, he’d realize how little he’d accomplished, how much there was to do, how outrageous it was that some poor slob was paying out one hundred and fifty dollars an hour for his fecklessness. Then the panic would start. Finally, toward evening, after an afternoon spent in futile attempts to justify his salary, he’d resign himself to the fact that today was not the day he came up with a case-breaking insight, found some overlooked and pivotal authority, turned around a losing cause. Instead it was a day he spent six hours poring over numbingly boring FCC reports only to find he’d been researching the wrong section of the Telecommunications Act, a day he realized he’d been charging his time to the wrong client number and spent four hours trying to pull the records from the depths of the computer system.”

Of another Morgan Siler lawyer, Roosevelt writes: “They warn you that law will divide you from your family, your friends, your hobbies. He had avoided this by having none. But no one tells you that it will divide you from yourself.” Despite digs such as these throughout the book, Roosevelt is surprised when reviewers and readers suggest he seems completely disillusioned by the legal profession. Slight in build and always soft-spoken, Roosevelt does not seem like someone who would take on the legal establishment so forcefully. “Everyone has taken it as bleak, but I didn’t intend it that way,” Roosevelt said. It is true that in his own observation of law firms, “people underestimate the amount of drudgery associates live with” and the personal struggles that produces. But he added: “People say you can do it for a few years and move on. But it does change you. You can’t necessarily set it aside.” But in his book, Roosevelt points the way to lawyerly salvation: pro bono work. The plot is built around two major cases the firm is handling, one the defense of a chemical company sued for toxic torts and the other a death penalty appeal handled on a pro bono basis. “Pro bono is where the young associate can exercise professional judgment and some independent moral judgment,” Roosevelt explained. After clerking for Souter, Roosevelt’s own taste of private law practice before entering academia was mainly at Mayer, Brown, Rowe & Maw in Chicago. Mayer, Brown was not the model for Morgan Siler, Roosevelt insisted. “I had a very good experience there,” Roosevelt said. “I did a lot of pro bono work.” His pro bono efforts included a prison rights case akin to the Supreme Court case in which he filed his amicus brief this year. “You can influence the firm,” he noted. “You can integrate the personal and the professional in a morally reflective way, a happy and ethical way.” The book, first published in hardcover last year, won rave reviews. Alan Dershowitz, writing for The New York Times, observed that the book “understands the culture of the law firm and takes us inside its gilded cage.” But the one that counted the most came from Souter. “He wrote me quite a nice note,” Roosevelt said with pride. Souter had expected not to like it — he’s not a fan of legal thrillers — but told Roosevelt he was “pleasantly surprised.” Roosevelt’s next book will emerge from the law-professor side of his brain. Titled The Myth of Judicial Activism, it will examine how the shibboleth “judicial activism” often mischaracterizes Supreme Court rulings. Planned for release in October by Yale University Press, the book will offer a new model for assessing the legitimacy of Court rulings. When a commentator accuses the Court of “judicial activism,” he said, it usually means only that the commentator did not like the result. A prime example, Roosevelt noted, was last year’s widely attacked ruling in Kelo v. City of New London, which allowed governments to exercise eminent domain to take private property, even when the property would only be transferred to another owner for private use. The decision was cited as an example of judicial activism, but, in fact, Roosevelt said, it was a paragon of judicial deference. The Court was deferring to the elected officials of New London, Conn., who had enacted an economic-development plan that led to the disputed taking of private homes. Justice John Paul Stevens, who wrote the opinion, said later that he thought what New London had done was bad policy, but the Court could not have substituted its judgment for that of the elected officials. “I am really struck by the extent to which judicial activism has become a political issue,” said Roosevelt. “The term is really being misinterpreted.” The book has already been praised for tackling the subject in language that is accessible to nonlawyers. But that should be no surprise. Whatever the format — thriller, television series, or legal tome — Roosevelt embraces each one of his projects as a way to reach as broad an audience as possible and influence the way people think about the law. Nearly a century after his great-great-grandfather coined the phrase “bully pulpit” in a different context, Kermit Roosevelt III is testing out some pulpits of his own.


Legal Times Supreme Court correspondent Tony Mauro can be contacted at [email protected].

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