Cubs prospect balances rigorous UChicago College education with baseball training

Unique contract supports Wilson Cunningham’s full-time enrollment as math major

Editor’s note: This story is part of ‘Meet a UChicagoan,’ a regular series focusing on the people who make UChicago a distinct intellectual community. Read about the others here.

On a rainy afternoon in Hyde Park last July, Wilson Cunningham got a life-changing call from the Chicago Cubs.

He had spent the day touring the University of Chicago campus with his parents, but the final day of the 2021 Major League Baseball draft was making it difficult to focus.

After quietly leaving the tour, Cunningham and his parents were waiting together in the UChicago Bookstore when the 6-foot-8 pitcher’s phone started to buzz. The Cubs had selected him in the final round of the draft.

An 18-year-old left-hander who took two years away from the sport in high school was about to become a professional baseball player—a career path that would typically preclude someone from pursuing education full-time. But thanks to an atypical contract arrangement offered by the Cubs, Cunningham could train and play as a member of the organization while pursuing a transformative undergraduate education at the University of Chicago College year-round.

“I love to learn, and I think that's the type of student that UChicago caters to,” he said. “The Core Curriculum really encourages you to expand your horizons and learn all sorts of subjects. It just stood out to me as a school for thinkers and for intellectuals, with a huge emphasis on free speech, and it was ultimately the best opportunity for me.”

More than a year later, as a student in the College studying applied mathematics, Cunningham spends about 20 hours a week adhering to a baseball training program prescribed by Cubs trainers and coaches, on top of his studies. 

Balancing those duties with the demands of a rigorous College course load hasn’t been easy. But like many of his classmates, his drive to challenge himself is what brought him to UChicago in the first place. It’s why he fits right in.

An unorthodox path

Growing up in Orange County, California, Cunningham devoted much of his youth to baseball, from tee-ball practices and games to middle school travel ball. By the time he reached high school, he was burned out, in part due to overuse injuries, leading him to step away from the sport.

During those two years away, he played golf and volleyball and ran track—hoping to have fun and decide if he only needed a break from baseball, or sports in general. 

After exploring many of his other interests, including piano and math, he began to miss baseball. Cunningham earned a spot on his high school team as a junior in spring 2020—and as a tall left-hander with a fastball close to 90 miles/hour, and plenty of room for further development, he quickly drew interest from several college baseball programs, including UChicago.

Awarded for excellence in math at his high school, Cunningham was primarily focused on academics during his recruiting process. Although he hadn’t ruled out playing professionally, baseball came a distant second to pursuing his goals as a student.

UChicago stood out to him as a possible landing spot for many reasons, starting with its smaller class sizes and emphasis on a well-rounded education. In the fall of 2020, he signed a letter of intent to play for then-coach John Fitzgerald and the UChicago baseball team.

A projectable arm

Cunningham planned to play for the Maroons until late June 2021, when he received an introductory pre-draft phone call from a California-based Cubs scout. The scout advised him to enter his name into the MLB draft and proposed the unique arrangement that would allow Cunningham to attend college. 

Standard minor league baseball contracts include a continuing education provision that provides players with funds to attend college, but only once they have accrued a certain number of years of service time. The Cubs offered to enact that provision for Cunningham at the start of his contract, allowing him to enroll full-time in the College with his tuition partially covered by the team. (This arrangement would void his eligibility to play at the collegiate level). 

“I first thought that their suggestion to enter my name in the draft was just getting me into the system so the Cubs could check up on me in a few years and see how I was doing,” Cunningham said. “But when they told us about the plan that they had in mind—which is the best of both worlds—it was just crazy.”

This proposal was not a promise from the Cubs by any stretch, however. During drafts, teams can change their plans at a moment’s notice, and there was always the possibility that another team would swoop in ahead of the Cubs to draft Cunningham.

As the draft stretched through its third and final day on July 13, 2021, Cunningham’s heart raced. Finally, picking at No. 604 out of 612 in the 20th and final round, the Cubs made their selection and called Cunningham.

“We look at our deal with Wilson Cunningham as investing in the whole person while also making a long-term investment for the team,” said Cubs President of Baseball Operations Jed Hoyer. “Throughout the organization we seek to communicate and work with players to help them grow off the field as well as develop on the field.

“It was clear that attending the University of Chicago to further his education was of utmost importance to Wilson and his family. We had the pleasure to work with them and create a deal that allows Wilson to achieve his goals in the classroom while also beginning his dream to pursue Major League Baseball.”

One year later

Cunningham’s first year at UChicago was a whirlwind. A typical weekday consisted of a morning workout at Henry Crown Field House, classes in the afternoon, and an intense throwing session immediately after class.

During a typical throwing session during the academic year, he starts with a meticulous warm-up routine then works with resistance bands and weighted balls to strengthen his arms. From there, he follows the Cubs training staff’s personalized throwing instructions, sticking to a plan he classifies as “quantitative and regimented.” This extensive, detailed training program includes additional daily arm care.

Cunningham said training alone was challenging, especially when Chicago’s winter weather forced him to work out indoors for much of the school year. And unlike the vast majority of pro baseball players, he’s also faced the pressures of navigating physics and calculus courses.  

“Obviously, it's been difficult, but that's what I knew going into this, and that's what I had hoped for,” Cunningham said. “I tend to pursue things that will be rewarding in the long run, no matter how hard they are in the short term.”

Now that the school year is over, he has reported to the minor league Arizona Complex League Cubs, where he is facing professional hitters for the first time. While the Cubs have given Cunningham the resources to help prepare him for the mental aspects of pitching, he’s also enjoying training with his fellow minor leaguers.

“There's something about being on the field with a team that’s essential to being the best pitcher you can be,” he said. 

Cunningham plans to earn his bachelor’s degree in 2025, after which he plans to take his baseball career as far as he can. Down the road, he hopes to put his UChicago degree to use too—possibly through a career in finance, or teaching at the college level. 

For now, with three years at UChicago ahead, he remains focused on the unique opportunity at hand. 

“I'll be walking down the hallways and hear two friends having a discussion about Aristotle, which is a pretty unique thing to come across on a college campus,” he said. “UChicago has really upheld its reputation for being a place with smart students that all bring something different to the table. It’s been a cool and interesting experience.”

—This story was also published on the University of Chicago College website.