For years, Kaleb Wing had been limited to playing the infield due to his undersized frame.
On the 2024 summer showcase circuit, a late high school growth spurt was adding new life to Wing’s tools. At tryouts for the Area Code Games, he threw harder from shortstop during infield drills than he ever had.
His invitation to the second round of tryouts brought an unexpected surprise: He was asked to get on the mound.
“It was pretty crazy to me, because I had never pitched before,” Wing said. “It was a shock, but I love this game and I want to continue to play it at the highest possible level. And if these evaluators are telling me that my best avenue may be on the mound, then I’m going to try and pick it up.”
Those evaluators were clearly onto something.
A year later, Wing was drafted by the Cubs in the fourth round as a righthander out of Scotts Valley High in California.
This winter has been Wing’s first solely focusing on pitching and just his second preparing to pitch at all. It surely helps that Wing’s father Ryan was a professional pitcher who reached Triple-A in 2008.
“Although he just started pitching in the last year or so, you don’t get the impression that he’s behind in any way,” Cubs scouting director Dan Kantrovitz said. “While he’s got plenty to still figure out, he’s a really thoughtful, smart, curious kid who is mature beyond his years.”
Since Wing signed, the Cubs have focused on adding calories and muscle to his 6-foot-2 frame during two offseason camps at their Arizona complex. Compared with pre-draft testing, he has added about 20 pounds, weight that is designed to help him handle the rigors of pitching a full season.
“I haven’t spent a lot of time on the mound,” he said, “and I think finding a consistent delivery that allows me to command my stuff is going to be the biggest piece.”