Cubs Sign the Most Creative Deal of the Draft with Wilson Cunningham

Wilson Cunningham after signing with the Cubs via Cunningham family

A special thanks to Wilson Cunningham for meeting with me for this interview.

Cubs draft Twitter was sent into a scramble in the 20th round of this year’s draft with those words. Another high school pitcher, but one that wasn’t on their radar. Who was this mystery pitcher? Standing 6’8″ with a very projectable frame and coming from an impressive high school, Wilson Cunningham has all the features you’d like to see from a draft pick. He also wasn’t listed on the primary draft ranking websites like Prospects Live or Baseball America. Cunningham was committed to the University of Chicago, an institution known for producing more Nobel laureates than future MLB players. The selection required a deeper dive.

Cunningham signed the most creative deal in the Chicago Cubs draft class, and after reaching out to a few contacts within the game, it’s a deal that no one could provide a similar example of seeing before. Unlike most players, Cunningham signed a contract with the Cubs, but he will be attending the University of Chicago as planned.

It was all a huge surprise, [but] a wonderful surprise…

Wilson Cunningham

Who is Wilson Cunningham?

Standing 6’8″ at 185 lbs. during his Senior year of high school, Wilson Cunningham’s frame may resemble a basketball or volleyball player rather than what one would expect on the baseball diamond, but the Cubs see untapped potential. Despite only throwing in the mid-80s with his fastball, the lanky lefthander offers no shortage of future physical projection. Cunningham is well aware he doesn’t light up the radar gun, but he is also attuned to the unique skills he brings when he steps out on the mound. “You look at the other guys in the organization or the other Draftees [interms of velocity]. I’m a little behind the curve there, but I think what I have going for me is my height [and my] left-handedness,” Cunningham said. “So, right now, as a pitcher, I’m really comfortable with my fastball. I’ve heard players on my team when we do intersquads say ‘hey, you hide the ball really well, or it’s really tough to hit off you even though you’re not throwing as hard as everyone.’ And I think, maybe, just maybe, releasing closer to the plate might help with that, just [using] my long frame. My fastball has tons of natural sink. It’s definitely not a true four-seam. It kind of runs towards the end of the bats and induces a lot of soft contact, which is really great.” 

Wilson Cunningham on the mound via Cunningham family

Though he didn’t discuss the concept by name, his long frame allowing him to release the ball much closer to the plate is an intriguing attribute. That concept is known as a pitcher’s extension. The Cubs organization is known to favor pitchers with a long extension and higher “perceived velocity” (the ball appears to be traveling faster to a hitter than it is). But Cunningham also fits the Cubs’ recent development model of targeting players who can make significant gains with proper instruction. After investing heavily in the Performance Science and High-Performance departments, the Cubs have another ideal player to build physically from the ground up. After speaking with Cunningham, he confirmed that he’s made significant strength and weight gains. He now sits over 200 lbs., with plenty of projectability remaining.

What is far more difficult to teach is a player’s intelligence and mentality. Though I can’t speak to the specifics about Cunningham’s demeanor on the mound, it shouldn’t come as a shock that the University of Chicago-bound student boasts a curious mind and a keen ability to understand the intricacies of advanced mathematics. The lefthander’s major as he enters his university years? Applied mathematics with a focus on economics. I would bet concepts such as spin rate, spin axis, induced vertical break, and tunneling won’t be too difficult to pick up. 

The Deal Coming Together

The Chicago Cubs’ scouting departments leave no stone unturned and have a very collaborative process in building their draft plans. There may not be a better example of incorporating both aspects into results than the selection of Wilson Cunningham. According to Cunningham, this process came together near the end of the draft cycle.

“About two and a half weeks before the draft, my dad actually got a call from the area scout (Evan Kauffman). He called me and said, ‘Hey, nice to meet you. I’ll be sending you an email. Just fill out [a draft prospect questionaire], and if there is a time, we can Zoom with your whole family later this week. And so that was a Monday, I believe, and then we set up the zoom for [that] Thursday,” Cunningham said.

Cunningham’s Zoom invite brought in high-level executives within the Cubs Scouting department, including VP of Scouting Dan Kantrovitz. But despite a very positive meeting, Cunningham didn’t leave the session feeling confident it would happen. “I honestly didn’t think I was going to get drafted. I thought that they were just getting to know me; maybe they keep tabs on me while I’m at school and kind of check up on me in a couple of years to see how I’m doing, baseball-wise. But they mentioned the plan a little bit about doing both, going to school, playing for the Cubs, [though] it was pretty vague on the logistics,” Cunningham said.

The Cunningham family already were planning to be in Chicago the week of the MLB Draft on a campus tour, and so the Cubs planned a tentative meetup at Wrigley Field on Sunday (the first day of the draft) if time would allow. 

 As it turned out, the scouting team was able to schedule the time. “A week later, we go to Chicago, and we’re at Wrigley. And, the day before Evan [Kauffman] texted me and said, ‘Yeah, you’re good to go. We can meet with you,'” Cunningham said. 

After being escorted by Scott Munson and Ben Kullavanijaya (Coordinator and Assistant in Amateur Scouting) up to the offices to meet Evan Kauffman, the Cubs brought in the real heavy hitters within the Cubs organization. If there was any question about how interested the Chicago Cubs were in Wilson Cunningham, it was quickly answered when both Kantrovitz and Cubs Assistant General Manager/Vice President, Pitching, Craig Breslow met with the Cunningham family. Without any time to lose on the morning of the MLB draft’s first day, the Cubs laid it out to Wilson and his parents. “They talked more about the plan and they said ‘Hey we’re really considering drafting you. They just went over the whole plan again and talked more [about the] details and everything,” Cunningham continued. After reaffirming his interest in pursuing baseball professionally, the Cubs told him to keep his phone on him on Tuesday, day three of the draft. 

The Waiting Game

As Wilson Cunningham and his family prepared for a life-changing day, he toured the University of Chicago campus trying to hold back nerves. According to Cunningham, “It’s Tuesday, and we’re actually on the University of Chicago campus touring the school as I had never seen it with COVID and everything. So [my family is] there, and we’re all on our phones on the draft tracker refreshing. I don’t know if I get drafted at all, or if it’s 10th, 12th, 15th, or 20th round. We just left the tour because we couldn’t handle it. We were super excited and angsty and everything. So we waited.” After what must have felt like an eternity, Cunningham finally was contacted by Evan Kauffman. “We sat down in this little café, and I got a call from Evan. I’m like, oh my gosh, oh my gosh, this is it. It was around the 15th round. And then he said, ‘Hey Wilson. We’re just making sure that you’re really seriously considering this course,'” Cunningham said.

His parents thought Wilson had been drafted there but to no avail. Time ticked by, and countless refreshes of the draft tracker later, Wilson Cunningham finally saw his name pop up as the 20th Round selection of the Chicago Cubs.

“The big day” via Cunningham family

Next Steps

The complexities of this signing meant that all the respective ducks needed to be in a row. The Cubs worked tirelessly behind the scenes and were in communication with the Cunninghams. First and foremost, the family wanted to make sure that Wilson could continue to attend school and have that school paid for by the Chicago Cubs as promised. 

It is common practice for Major League organizations to offer signed players funds to pursue college education if the player retires. What is truly unique about this deal is that the Cubs pursued language that would specifically allow Cunningham to tap into those resources immediately rather than within two years after a player retires. 

“College Scholarship Plan (CSP) or Continuing Education Program (CEP) funds to help you attend an institution that offers training for personal and professional development. A CSP provision would allow you to attend a university or college, provided your studies are in pursuit of an undergraduate degree.”

With such a special deal, an even more personalized training regimen was required. According to Cunningham, he is off to the University of Chicago to begin fall classes this September through the end of the academic year (in June). However, he will still dedicate time to his baseball activities. “I will be at school full-time student at school, and I’ll be training remotely with the Cubs. It does also helps to be in Chicago with the staff there. I’ll be on the lifting [and] throwing program. I’ll be checking in with people,” Cunningham said. “Then over spring break and over the summers (and maybe even some long weekends here and there), I’ll be in Arizona with the ACL Cubs as a full-time baseball player.”

The Cubs didn’t enter the 2021 Draft with the most bonus pool money or draft selections, but they worked behind the scenes to bring in an amazing group of players. To accomplish this, they had to be creative in their bonus pool allocations and explore unique avenues to bring in projectable players, like Wilson Cunningham. 

Wilson Cunningham would like to thank his family, friends, and his coaches, Glenn Zielinski, Brett Kay, and Blake Hawksworth, for helping him prepare for a future in baseball and in his studies. He would also like to thank Cubs officials Evan Kauffman, Dan Kantrovitz, and Craig Breslow for making sure that the deal was a win-win [for himself and the organization]. Most importantly he’d attribute this whole situation to God.


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