Wilson Cunningham

Wilson Cunningham, Class of 2025, during a solo training session. (Photography by John Zich)

Ballpark figure

In his spare time, applied math major Wilson Cunningham, Class of 2025, trains for the Cubs.

Last July Wilson Cunningham, Class of 2025, got a life-changing call from the Chicago Cubs.

It was the final day of the 2021 Major League Baseball draft. Cunningham, in Hyde Park on a campus tour with his parents, was finding it difficult to focus.

Finally, his phone buzzed. The Cubs had selected Cunningham—a 6'8" left-handed pitcher—in the final round. Typically, playing professional baseball would make it impossible to pursue a college education full-time. But an unusual contract arrangement allows Cunningham to train and play with the Cubs while studying at UChicago.

Growing up in Orange County, California, Cunningham devoted years to the sport, from T-ball to middle school travel ball. By high school, he was burned out, in part due to overuse injuries. So he quit.

As a freshman and sophomore, Cunningham played golf and ran track—hoping to have fun and decide if he needed a break from baseball, or from sports in general. He spent more time on his other interests, including piano and math.

But he missed baseball. Cunningham earned a spot on his high school team as a junior in spring 2020. As a left-hander with a fastball close to 90 miles an hour, he quickly drew interest from college baseball programs. (Left-handed pitchers are sought after, as their pitches often befuddle right- and left-handed hitters alike.) Until June 2021, he had planned to play for the Maroons.

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Then he received a phone call from a California-based Cubs scout. The scout advised him to enter his name in the draft and proposed the unique arrangement allowing Cunningham to attend college.

Standard minor league baseball contracts include a continuing education provision, but only after playing for a certain number of years. The Cubs offered to enact that provision for Cunningham at the start of his contract, allowing him to enroll in the College with his tuition partially covered by the team. (This arrangement voids his eligibility to play at the collegiate level).

At first, Cunningham assumed the Cubs would check up on him in a few years. “But when they told us about the plan that they had in mind—which is the best of both worlds—it was just crazy,” he says.

The proposal was not a promise, however. During drafts, teams can change plans. There was always the possibility that another team would swoop in. Finally, picking at No. 604 out of 612 in the 20th and final round, the Cubs called Cunningham.

Cunningham’s first year at UChicago was a whirlwind. An applied mathematics major with a specialization in economics, he spent 20 hours a week doing baseball training on his own. A typical weekday consisted of a morning workout at Henry Crown Field House, classes in the afternoon, and an intense throwing session after class.

During throwing sessions, he starts with a dynamic warm-up, then does strength training with resistance bands and weighted balls. From there, he follows the Cubs training staff’s personalized throwing instructions, sticking to a plan he calls “quantitative and regimented.”

Training alone has been challenging, especially during the winter, Cunningham says. And unlike other pro players, he’s faced the pressures of physics and calculus classes. “Obviously, it’s been difficult,” he says, “but that’s what I knew going into this.”

During the summer, Cunningham plays for the Arizona Complex League Cubs, going up against professional hitters. “There’s something about being on the field with a team that’s essential to being the best pitcher you can be,” he says.

After graduation, Cunningham hopes to take his baseball career as far as he can. Longer term, he’s considering a career in finance or academia.

For now, with three years at UChicago ahead, he remains focused on college life. “I’ll be walking down the hallways and hear two friends having a discussion about Aristotle,” he says. “It’s been a cool and interesting experience.”