The University of Chicago Law School Federalist Society

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Alumni Spotlight

Each month, we'll highlight a different alumni of the University of Chicago Federalist Society. These alumni range from government officials to Biglaw partners to think-tank heroes. Check back often for new entries!

February: Ilya Shapiro

Where do you work now?
I'm at the Cato Institute - where I've been for over a decade now advancing liberty at the intersection of the legal, academic, media, and political worlds. That wasn't necessarily the plan when I joined, but it's a great gig and nobody's been able to give me a better offer.
What position(s) did you hold in Fed Soc? Alternatively, what other organizations were you involved in during law school?
Fed Soc officer slots were (and I assume remain) very competitive, so I actually didn't have one. (More than 500 Fed Soc speaking events later, I feel that I've more than made up for that!) I was also involved in the Edmund Burke Society, moot court, intramural sports, one year each on the law school musical and CJIL, and, of course, bar review.
Please name your least favorite Constitutional Amendment and why.
I'll have to go with a three-way tie among the 16th, 17th, and 18th amendments. There have been worse things in the development of American politics and society than the income tax, direct election of senators, and alcohol prohibition, but these are the worst things that have made it explicitly into the Constitution.
What was your most memorable law school moment?
Undoubtedly it was getting hooded by Prof. Epstein on graduation day, which was the cherry on top of the whole journey. He told me that day to start calling him Richard, but it took me about a decade—during which I edited a couple of his articles and briefs—to do so.
What is the best career advice you've received?
I'm not sure I ever got any particularly good career advice, at least not in law school. Whoever turned me on to clerkships—which I'd never heard of before my 1L year—was certainly key. You know, I used to say "follow your passion and do it well," but that doesn't help much if you don't know what your professional passion might be. I now tell people, particularly those who see what I do and (rightly) think of it as a dream job, is to think what it is you want to do—help a business prosper, influence policy, make a lot of money, be intellectually stimulated, whatever—set long-term goals meant to achieve that, and adjust as life presents opportunities and teaches you what you really want.
What person in history would you love to have dinner with?
James Madison. I'd want to discuss his theories of and experience in government, and then ask him to reflect on how things have turned out and what needs to be done to fix them.