Career
My Baseball Journey
Credit: Freek Bouw

Credit: Rich Biesterfield
I've played baseball for almost my whole life and I’ve had the privilege of pursuing a career as a professional baseball player, a dream I’ve carried since I was a kid. Out of high school, I was drafted by the Chicago Cubs in the 2021 MLB Draft. The Cubs and I were able to come to a unique agreement: I would be able to pursue my education full-time while still playing in their Minor League organization—a detail in my contract that has been fundamental to my personal success in these past years.
Spending extended offseasons at school and away from the coaching and resources (and catch partners!) was frustrating at times, as I felt that I was falling behind in my performance. That being said, I am very grateful for my time at UChicago; I made some amazing friends, grew deeper in my faith, unlocked myriad opportunities, and I am now much wiser and resilient.
Now that I've graduated, I am giving baseball my best shot. With so many unknowns, I don't know how far baseball will take me, but I am doing all that I can to take my fullest advantage of this opportunity while it still lasts.
Featured In
"The Unique Dual Life of ‘Brainiac’ Pitcher Wilson Cunningham"
— Chicago Tribune
"Wilson Cunningham on Math, Baseball, and the Cubs" (Podcast)
— Institute for Mathematical and Statisctical Innovation
"Too Good for DIII: The Curious Case of Wilson Cunningham"
— The Chicago Maroon
My Academic Interests
I thrive when I am intellectually stimulated. I'm always curious; I love to challenge myself and learn new things. Though my academic interests are broad, I've always been particularly drawn to numbers.
At UChicago, I earned my B.S. in Computational and Applied Mathematics, which was a great mix for me: pure math, statistics, and computer science. I was also able to specialize in Finance, which sealed all of my strongest interests into my major and gave me tangible tools for a future career.
What made my time at UChicago truly special, though, was the breadth of subjects in the curriculum. Even as a STEM major, I took lots of humanities classes that allowed me to explore my interests beyond math. In those courses, I engaged deeply with history, art, literature, and philosophy, and I became a much stronger writer and thinker because of it.
I hope this website can be a genuine reflection of these interests: I'm sharing my passion for reading, I used my STEM skills to code this site from scratch, I spent a lot of time styling it to look just right, and I had a blast creating it.
What's Next?
With so many unknowns—injuries, performance, and ever-changing team rosters—I can't realistically predict where my baseball path will lead. So, it's in my best interest to plan for my career beyond playing baseball.
Should my baseball career end soon, I plan to pursue a career in finance. At the moment, I haven't decided on a specific role or sector, but I believe fields like quantitative trading and research, equity research, and asset management align best with my interests and strengths.
I’m also drawn to many other areas beyond finance, including academia, and I’m constantly exploring new ideas and possibilities. I have a wide range of interests and haven’t settled on just one path (yet!), but that’s part of what excites me about the future.