UChicago student. Math whiz. Professional baseball player for the Chicago Cubs. One person being all three seems paradoxical. But that’s exactly what Wilson Cunningham is: a paradox. He didn’t touch a baseball in his freshman or sophomore year of high school, yet managed to get drafted by an MLB team just two years later. He is attending college and has rigorous academic commitments, yet continues to train professionally with the Cubs at the same time. He is extremely accomplished and decorated with achievements across fields, yet incredibly humble and one of the nicest people you could ever meet. Welcome to the curious case of Wilson Cunningham.

Wilson Cunningham has a special contract with the Chicago Cubs, wherein he is part of the Cubs’ minor league system while also attending college at the University of Chicago. Choosing between college and going professional is one of the toughest aspects of any young draftee’s career, but thankfully, Cunningham never had to make this choice. In this interview, The Maroon dives into Cunningham’s childhood, baseball career, life at UChicago, and everything in between.

CHICAGO MAROON: Thank you so much for being here today! Let’s start with a bit about your childhood. Can you share something about your early days in baseball and what inspired you to pursue it professionally?

Wilson Cunningham: I’ve been playing baseball ever since I could hold a baseball, starting in T-Ball as a 4–5-year-old. My childhood dream was to be a professional baseball player. Unfortunately, in middle school, I picked up a few injuries and started getting pretty burnt out with baseball. Also, I’d started growing a ton, so I decided to branch out and try a few different sports. I tried track, golf, volleyball, which were all fun, but I really missed baseball and came back to it junior year. So I was very rusty my junior year and had to work a lot on getting my rhythm back. A good thing was that my high school had a really good team, so there were a lot of scouts at our games, which allowed me to be noticed even without being a huge draft prospect.

CM: Were there any particular players or role models who influenced your playing style and career aspirations?

WC: I was always a big fan of lefty pitchers, being one myself. Especially tall lefties, like Chris Sale, Randy Johnson, Jon Lester and C.J. Wilson, were players that I emulated in my game. [Cunningham is 6’8”.] But outside of players, I had a whole slew of coaches that were formative to who I am, both as a player and a person. My pitching coach [during middle and high school], Glenn Zielinski, was very formative in not just my love for baseball but also in me growing as a person. Another coach was J.P. Glasscock, who really helped me knock off my rust in junior year and… really helped my game. And of course, my parents, who were always very enabling and supportive of me and my career. My gratitude towards them pushed me to always work harder.

CM: What were some of your hobbies or interests that helped you unwind and relax after such rigorous training throughout your childhood?

WC: I’d play around a lot with my friends, a lot of pickup basketball, tag, and biking around. I used to play the saxophone, but never got super into it. But when I got an ankle injury in eighth grade and couldn’t do sports anymore, I started playing the piano sitting at home and ended up playing classical piano throughout high school. So piano was definitely my biggest time-out from baseball and school.

CM: What has been the most memorable moment in your baseball career so far, and why?

WC: They have this massive tournament in Cooperstown [an upstate New York town where the Baseball Hall of Fame is located] for middle schoolers. There are hundreds of teams from across the country. So my travel ball team played in that tournament, and we actually ended up winning it! So that was really cool.

CM: What would you say is your biggest strength on the field?

WC: My frame. Being 6’8” and a lefty definitely help me a ton as a pitcher. Having my release height and extension a bit higher allows me to release the pitch closer to the plate, increasing my pitches’ perceived velocity. I feel like that’s kind of unfair because I didn’t have to work for my height or left-handedness, [laughs] but they are probably my biggest strengths.

CM: Have you been making any changes to your game recently? You’d mentioned working on your fastball?

WC: Yeah, I’ve been making a ton of adjustments to my pitches. I added a lot of velocity to my fastball this summer, hitting 94 miles per hour now [up from 88 during Cunningham’s first year at UChicago]. I’ve also put on a good amount of muscle and cleaned up some mechanics, which really helps my velocity. I also recently added a cutter, which is also a very effective pitch

CM: Your special contract with the Chicago Cubs is so intriguing. Can you talk us through the contract and how it panned out?

WC: So the Cubs scouts had talked to me before the draft about whether I’d be willing to leave UChicago if they signed me, and I had made it clear that it would have to be a life-changing amount of money for me to even consider not going to UChicago [laughs]. So they started brainstorming ideas that would allow me to attend college here while also being part of the organization, and they came up with the idea of this contract. I do a training program with the Cubs while also attending classes here. So basically, I get the best of both worlds!

CM: How does your training schedule look like here? Do you train with UChicago coaches or Cubs or a mix of both?

WC: My programming is all through the Cubs’ coaching and strength and conditioning staff. So I have a weightlifting program, a throwing program, some sprint work, and some arm care to make sure everything is healthy, and that’s all through the Cubs. I do all that on campus, but mostly on my own.

CM: Why UChicago?

WC: UChicago is such a prestigious institution and it was a great fit for me because at the time, I wasn’t too sure about what careers I wanted to pursue other than baseball, and so the Core and liberal arts curriculum really stood out to me. Also, I’d never been to the Midwest and was excited about exploring Chicago! So I was really excited about attending college here and the Cubs knew that while drafting me.

CM: What are your long-term goals in baseball or your career generally? Would you maybe want to combine your interests in baseball and math or finance and become a General Manager?

WC: Yes, for sure that would be great [laughs]. I mean, goal number one is still being an Opening Day starter at Wrigley Field. I want to take baseball as far as it’ll take me, and only think about other potential careers if that doesn’t work out for some reason. But yes, it’d be great to still work in sports. Front office work would be right up my alley.

Rapid Fire:

What was your uncommon essay topic? The Miles Davis quote essay. I have no idea what I wrote though [laughs]. 

Favorite hang out spot on campus? Hutch and the Hutch quad, good food—the Saffron Butter Chicken is great.

Best class you’ve taken at UChicago? Visual Language: On Images for the Arts core.

Reg or Mansueto? Reg.

Ratner or Crown? Crown all the way. Every day of the week.

Best dining hall? Bartlett, I like the Taco Station.

One RSO you’re passionate about? Fellowship of Christian Athletes, I’m the Communications Chair.

Favorite player on the current Cubs team? Justin Steele, lefty pitcher. Also Luke Little, he started the year in High A and made it all the way to MLB. I’ve spent some time with him over in Arizona, so I’m rooting for him.

World Series predictions for next year? Cubs win.