Assistant U.S. Attorney Andrew Boutros '01, 'Silk Road' Prosecutor, Reflects on Career Path

Andrew Boutros

Andrew Boutros '01, a first-generation American, counts among his successes attaining a conviction for the world's largest drug trafficker.

October 2, 2015

Called to Serve is a series of Q&As with young UVA Law alumni working in public service careers.

As assistant U.S. attorney in the Chicago office's Financial Crimes Section, University of Virginia School of Law alumnus Andrew Boutros '01 investigates international fraud and cybercrime, and prosecutes business organizations and corporate executives. Previously, Boutros was in private practice on the opposite side, as a white-collar defense attorney. He has also worked as a Foreign Corrupt Practices Act practitioner, litigator and compliance counselor.

In 2015, Boutros was selected for the Federal Law Enforcement Officers Association National Prosecutorial Award. He was recognized in part for his role in prosecuting and winning a conviction of the world's largest drug trafficker on the dark website "Silk Road," described at the time as the most sophisticated and extensive criminal marketplace of its kind on the Internet.

Boutros was elected to the American Law Institute in 2015, after which the organization's quarterly newsletter published a Q&A with him. In the excerpt below, Boutros reflects on his career and time as a student at UVA Law.

You have been a federal criminal prosecutor in Chicago for almost eight years, and before that you were in private practice with a prominent firm in Washington, D.C., representing corporations and executives as a white-collar defense attorney, FCPA practitioner, compliance counselor and civil litigator. Why did you decide to become a prosecutor?

I never had the extraordinary honor of wearing the military uniform, but as a first-generation American, I had a strong desire to serve this great country, give back and at some level make a difference. After becoming a lawyer, and as I handled high-profile white-collar cases in private practice, I realized I could use my legal training, skills, and passion to represent the United States as a prosecutor. It became something I very much wanted to do, and I especially wanted to investigate and prosecute complex, sophisticated white-collar cases. But, as luck would have it, the timing was a bit off; I applied to become a prosecutor during a hiring freeze. Notwithstanding that, I was really committed to serving and willing to move almost anywhere the opportunity would take me. When the freeze lifted, then-Chicago U.S. Attorney Patrick Fitzgerald was the first to make me an offer; I gratefully accepted, and have remained in Chicago as a prosecutor since.

Since becoming a prosecutor, you have led what the national press and legal commentators have described as some of the largest and most complex international fraud and cybercrime investigations and prosecutions. How have you successfully investigated and prosecuted such high-profile cases?

Winston Churchill famously told students of the Harrow School in 1941, "Never, never, never, never — in nothing, great or small, large or petty — never give in, except to convictions of honor and good sense." My parents raised me to believe that one person can make a difference. As a prosecutor, this translates into a belief that one should not easily give up on a worthy case — particularly one with identifiable victims — just because it may be tough, prolonged, untraditional or present an uncertain outcome. I like to think that this mindset has served me well. And it of course helps when the federal agents with whom you work as part of a team are among the best in the business. For example, some of my most significant cases have been with phenomenal federal agents of the Department of Homeland Security in Chicago. Together we've twice successfully prosecuted what are billed as the largest criminal trade fraud cases in U.S. history, as well as the largest drug trafficker in the world on Silk Road, which has been described as among the most sophisticated dark websites of its time. I am very proud of these successful prosecutions, will always be grateful for the camaraderie and selflessness of the agents I had the privilege of working alongside, and will always be gratified by the positive difference these prosecutions have made to so many.

You have worked as a defense attorney representing corporations facing high-stakes investigations, and you currently work as a prosecutor who leads such investigations. How valuable is it to have worked on both sides of the aisle? How specifically do your experiences in private practice inform your work as an investigator and prosecutor?

My time in private practice has immensely contributed to my work as a prosecutor. Those prior experiences, and the lessons I learned, inform my strategic decisionmaking throughout all phases of an investigation and prosecution. More specifically, they also allow me to put myself in the "defense's shoes" when I make a request, issue a subpoena, obtain a search warrant, take a position or weigh options. Conversely, I feel I am also able to better assess the claims and challenges facing opposing counsel. Simply stated, in my view, a prosecutor with substantive, in-the-trenches private-practice experience has the advantage of being able to "think like a defense attorney," while at the same time being able to credibly identify with, and relate to, opposing counsel.

Think back to your days as a student at the University of Virginia School of Law. Who was your favorite professor and why?

UVA Law is chock-full of dynamic professors, who are as caring as they are accomplished. That said, I really enjoyed learning from Professor Jeffrey O'Connell, who until he passed away in 2013, was one of the leading lights of the insurance and tort bars. Having created the theoretical underpinnings for no-fault insurance, Professor O'Connell was able to import the challenges of the real world into the classroom, where we discussed both problems and solutions. In doing so, he offered wonderfully practical insights, while simultaneously maintaining a demanding academic setting. I not only took Professor O'Connell's advanced torts course, but I later became his research assistant. And, together, we authored a comprehensive article on certain aspects of tort reform that was published by the Notre Dame Law Review — an experience that was both rigorous and educational. All these years later, I am very grateful for the time and energy Professor O'Connell invested in me. I believe I am a better lawyer for having studied under his care.

You clerked for Judge Eugene E. Siler Jr. on the U.S. Court of Appeals for the Sixth Circuit. Have you continued to stay in touch with Judge Siler? What is the most lasting piece of advice he gave you?

Judge Siler is a role model, mentor and trusted friend. He is not only a legal giant, but a wonderful person. All these years later, he and I have remained in close contact. When you clerk for Judge Siler, you learn that he is a man whose actions transcend words. His most lasting piece of advice came in the form of me watching firsthand his never-ceasing respectful treatment of others. And by others, I mean everyone, whether from law or life. The lesson to me was that to be a good effective lawyer, one must treat others well, including those with whom one disagrees — and perhaps especially those with whom one disagrees. And perhaps as a variation on this theme, I also learned that an effective advocate disagrees with a position — not the person.

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