Drew Basile, ’29, has taken an unconventional path to UChicago Law. A University of Pennsylvania graduate and Barry Scholar at Oxford, he has also won seven games on Jeopardy!, competed on Survivor, and worked as a freelance writer. We spoke with Basile about his path to law school, what he learned from Survivor, and why UChicago Law was a “no-brainer.”

Tell us a little about your background and the path that led you to law school.

After undergrad, I studied at Oxford for two years, and I also appeared on some reality TV shows. Most recently, I’ve been a fact-checker and a writer.

What are one or two professional, academic, or personal experiences that have most shaped who you are, and why?

Competing on Survivor was a big one. The show is 100% real—way realer even than it looks on TV—and it takes about a year afterwards to fully recover. But it also taught me an openness to adventure and a stick-to-itiveness that I don’t think I’d have otherwise.

What inspired you to pursue a legal education?

On one level, I always knew I’d be a lawyer. I come from a family of attorneys, and I love the intellectual work that law entails: the analysis, logical thinking, rhetoric, etc. In short, it seemed like a natural fit.

What areas of law or legal issues are you most interested in exploring?

I like to keep somewhat of an open mind about this, but I do think I want to litigate. Academically, I’m excited to explore Chicago’s offerings in law & philosophy. 

Why did you choose the University of Chicago Law School?

This was a no-brainer. I’d always wanted to be at the University of Chicago, and I admire the Law School’s academic rigor and small class sizes. Also, growing up around Detroit, I have a lot of family and social connections in the Chicagoland area.

What impact do you hope to have with your legal education?

I think the world’s changing, and that there will be a growing need for the law to adapt and respond to developments like AI. It’d be great if, whether in research or in my career, I could contribute in some small way to these questions.

What are you most excited to experience as a UChicago Law student?

The people. It was nice to meet everyone during the admitted students programming, but I can’t wait to properly join the community on campus.

Do you have anything specific on your bucket list for your first year?

Eat lots of Chicago-style pizza.

What are some of your hobbies or interests outside of school and work?

I’m a big reader (currently: Fred Exley and John McPhee), and I love a good game of bar trivia. Hopelessly addicted to the NYT Puzzles app.

What's a fun fact about you that your classmates might be surprised to learn?

I traveled Goethe’s Italian Journey route for a summer my junior year in college. 

Is there anything else you'd like to share with the UChicago Law community

Excited to meet you all! If you see me (I’m really tall), come up and say hi!