Meet the Class: Simon Whiteman, ’27

Former Professional Baseball Player Ready to Take on Business Law

Simon Whiteman catches a baseball

As a former Major League Baseball player with a chemical engineering degree from Yale, Simon Whiteman, ’27, has an unusual CV. The Trumbull, Connecticut native is excited to put his intellect and the skills he learned as an athlete to work in the legal field.


Please describe your professional background and path.

I graduated from Yale University in 2019 with a degree in chemical engineering. One month later, the San Francisco Giants selected me in the ninth round of that year’s amateur draft. I played professional baseball in the Giants’ organization for five years across four levels as high as AA.

What key experiences have shaped you?

Playing professional baseball exposed me to a host of different personalities, backgrounds, and cultures. I learned how to collaborate with peers from many walks of life. Living in various states and playing on many teams with players of assorted ages, I learned how to communicate and compete alongside many different teammates.

What motivated your decision to go to law school?

My approach to problem-solving is extremely analytical, stemming from my engineering background as an undergraduate. Studying law will give me an entirely new toolset to tackle problems at the intersection of business and policy.

Why did you select the University of Chicago Law School?

I am looking forward to learning from brilliant faculty who are at the top of a myriad of fields. Additionally, the University’s commitment to the pursuit of truth through free speech discussion excites me.

What do you plan to do with your legal education?

I’d like to work as in-house counsel for a corporation, executing strategies and making decisions while using my law background to structure business solutions.

Simon Whiteman poses for the camera.

What is the thing you are most looking forward to about being a law student?

For the last five years, I’ve been training and competing physically, using my intellectual abilities in service of optimizing my physical strength, mobility, and efficiency. I’m looking forward to competing intellectually using my mental skillset for its own benefit.

What are some of your hobbies or interests?

Outside of baseball and physical fitness, I’m interested in psychological horror in both literature and film, and the gothic genre.

What is a “fun fact” about you?

In my last year of professional baseball, in AA, my top sprint speed of 31.3 ft/sec would have placed me top three in the Major Leagues. I stole ninety-seven bases with the Giants and another seventy in a four-year college career.