Career

My Baseball Journey

Credit: Freek Bouw

Credit: Rich Biesterfield

I played baseball for almost my whole life, and I had the privilege of pursuing a career as a professional baseball player, a dream I had 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 was 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.

After graduating college, I gave baseball my best shot, but in August 2025, my career came to an end. Due to struggles with ongoing injuries and my own performance on the field, I had not panned out to be the player I quite hoped to be.

Despite my career coming to an end sooner than I had hoped, I am immensely grateful for my experiences in professional baseball. Being in the Cubs orgnaizaiton for 4 years, I cultivated relationships with teammates, coaches, and other staff. I made friends, found mentors, learned valuable lessons, became more disciplined, principled, and healthy, and was able to do so while playing a sport I love.

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?

For inquiries or résumé requests, please message me on LinkedIn or email me at wilson@wilsoncunningham.com.