Lots of college students spend their summer jobs blowing whistles at the local swimming pool or making sundaes at Ye Olde Ice Cream Shoppe. Wilson Cunningham is spending his throwing 90 mph fastballs to professional hitters.
The tall and lanky 19-year-old is a left-handed pitcher in the Chicago Cubs’ farm system and a sophomore-to-be at the University of Chicago, with a “substantial” chunk of his tuition paid by the club. The arrangement calls for him to work out on his own during school months — his pro status means he’s not allowed to play college ball — and report to the Cubs’ Arizona training center when classes are out.
“That’s like the best of both worlds,” Cunningham said in a recent interview. “It’s something I could only dream about.”
The deal allows him to simultaneously pursue a degree at one of the nation’s top schools while getting the training that one day might propel him to the big leagues. It’s not an unprecedented agreement — other players, including 2000s-era All-Star Shawn Green, have been able to attend college after signing with a team — but the Cubs don’t recall offering a similar one.
Jim Callis, a draft expert with MLB.com, said that compared with the millions of dollars splashed on top picks, Cunningham’s deal is a modest wager that could profit everyone involved.
“You’re not talking about a very big investment,” he said. “And obviously they feel like there’s the potential for a payoff in the end.”
Cunningham grew up in Southern California and played baseball as soon as he was old enough to hold a bat. But after a childhood filled with Little League and travel ball, he gave up the sport when he got to his midteens, partly because of injuries, partly because he was growing faster than a dandelion in a trough of Miracle-Gro (he now stands 6-foot-8).
He said the two-year hiatus rekindled his love of the game and took stress off his arm. He joined the team at JSerra Catholic High School, a baseball powerhouse that routinely attracts the attention of Division I college coaches and professional talent evaluators.
Cunningham’s skill and physical stature caught the eyes of the Cubs during his senior year. As scout Evan Kauffman and vice president of scouting Dan Kantrovitz stood behind home plate one day watching him throw, an idea formed.
“I said, ‘Where’s Wilson committed?’ and (Kauffman) said, ‘The University of Chicago,’” Kantrovitz recalled. “And so a light bulb kind of went off in my head. I was like, ‘Well, that’s interesting. I wonder if there’s some kind of synergy we could make work, knowing he’s going to be in our own backyard?’”
Baseball Almanac lists just nine Maroons who have made it to the big leagues, the last in 1945, but Cunningham, who describes himself as “kind of a brainiac,” was hesitant to give up academics to chase a pro career. So when the Cubs offered to let him do both, he was sold.
“That was extremely exciting,” he said. “It was definitely a deal that I could not pass up.”
The Cubs took Cunningham in the 20th and final round of the 2021 draft. Few knew much about him: One website rated him the 505th best left-handed pitching prospect in the country, and another called him “a total shocker of a pick.”
Cunningham’s family was almost equally surprised.
“I think initially it caught us off guard, to be quite honest with you,” said his father, Jay. “Every kid wants to be a major league pitcher, but this all came together in just a matter of weeks.”
Cunningham received a $10,000 signing bonus along with a partial tuition payment. (Kantrovitz would not reveal the amount, but the full sticker price is about $60,000.) He spent about a month at the Cubs’ Arizona facility before heading to Chicago.
There, he settled into a schedule that included a morning workout, midday classes and afternoon throwing, often with members of the university’s baseball team, before he studied into the night.
The Cubs designed his workouts, he said, and he checked in with the team’s pitching and strength coaches weekly. Eating has also been a big part of the plan: Cunningham said that in the last year he has added 20 pounds to his frame.
He spent school breaks at the Cubs’ Arizona training complex and returned there this summer to play Rookie ball. So far, he has pitched 1 2/3 scoreless innings with three strikeouts.
“We couldn’t be more thrilled with the progress he’s already made,” Kantrovitz said. “We’re going to keep being really patient with him and make sure that as the next year unfolds we’re doing what’s best for him and his development. Hopefully, we continue to see the gains we’ve seen up to this point because it’s exciting.”
Cunningham is still a long way from the Show, but Callis said there’s reason for hope. Every year, a few players drafted in the 20th round make it to the major leagues (White Sox pitcher Matt Foster is one of them) and Cunningham, with his towering height and improving velocity, has been lauded for his “projectability” — scout-speak for potential.
Cunningham is studying computational and applied mathematics at the University of Chicago, demonstrating an analytical mindset that Callis said could be a good match for the Cubs and their vaunted Pitch Lab, which uses high-speed cameras and other gizmos to capture the fine mechanics of a throw.
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“There’s more of a scientific process in baseball now than there was 20 years ago,” Callis said. “You’d think a really intelligent player would do well in that environment.”
Kantrovitz said Cunningham’s brain power and discipline have made the arrangement work.
“You can imagine it working on paper, but until you get a chance to sit down and talk with Wilson, (you won’t) understand how he thinks, how impressive of a kid he is, how motivated and how intelligent he is,” he said. “That just goes hand in hand with what he’s studying in school — how we can sort of synthesize and incorporate the information we’re throwing at him because it’s an unconventional setup.”
Cunningham said the two worlds he inhabits have much in common, with each filled by unique and ambitious people. That has made it easy to go back and forth.
“It hasn’t been too much of a shock, I guess,” he said. “Just fewer conversations about Aristotle and more about Jacob deGrom.”