When Jamie Orenstein (’87), who was sworn in as a magistrate judge last spring, worked as a prosecutor, he helped convict mob boss John Gotti. Later, Orenstein was detailed to Denver to serve as one of the prosecutors who convicted Oklahoma City bombers Timothy McVeigh and Terry Nichols. During his years in the Eastern District U.S. Attorney’s Office, he rose to the position of deputy chief of the Organized Crime and Racketeering Section.
The Oklahoma City bombing case, more than any other, highlighted the tension between public duty and private conscience for Orenstein, an opponent of the death penalty, who frequently writes and speaks on the topic. “When I signed up for the system, I signed up for its rules,” he says of his stint as a federal prosecutor. Even though he thinks the death penalty is a bad choice for society, given that the Oklahoma City bombing was, at that point, the single most horrible criminal act committed on U.S. soil, it was important to pursue the death penalty against McVeigh and Nichols; otherwise, it would be difficult ever again to seek the death penalty in some less heinous case. A prosecutor cannot selectively opt out of the system he is defending, he notes.
Orenstein’s thoughtful approach to his duties as a prosecutor garnered him numerous awards and commendations, including twice receiving one of the Justice Department’s highest honors, the Attorney General’s Award for Distinguished Service. Following his Denver assignment, Orenstein served in the Department of Justice’s (DOJ) Office of Legal Counsel, advising the president and the attorney general on constitutional law. From 1999 to 2001, he served as associate deputy attorney general and chaired the DOJ’s working group handling the civil litigation and internal and congressional inquiries arising from the incident at the Branch Davidian compound near Waco, Texas. He also advised former Attorney General Janet Reno on criminal law matters, including the death penalty. “Janet Reno is personally opposed to the death penalty but sought it more than any other attorney general in history because she did her job in good faith,” Orenstein says. “That’s the tough part of public service.”
Orenstein eventually returned to New York City, his hometown,for a stint as a partner at Baker & Hostetler doing white-collar criminal defense work and corporate investigations. Orenstein also rejoined the Law School’s adjunct faculty, where he co-teaches the popular Complex Federal Investigations seminar with former Eastern District colleague, and now U.S. District Court Judge, John Gleeson. Many of the crowd that sparked Orenstein’s interest in criminal law are still here, like adjunct S. Andrew Schaffer and the Edwin P. Webb Professor of Law David Richards, and he is impressed by the current diversity of faculty and course offerings. Reflecting on his academic experience, Orenstein comes back to the professors who “seemed to really enjoy teaching and were interested in the law as something that can and should make sense, that is an active force in society, not just a set of rules on the back of the game board.” Reminiscing about Schaffer’s criminal procedure class, Orenstein recalls the excitement being palpable. “I was sitting in class on the day that John Gotti beat his first criminal case on March 13, 1987,” Orenstein says, “and all I kept thinking was I hope this guy is around when I’m a prosecutor so that I can get a piece of him.” Five years later, the jury was issuing a guilty verdict in the Gotti case—tried by Orenstein and Gleeson.