Quick Take
Scotts Valley High School shortstop-turned-pitcher Kaleb Wing spent the summer and early fall playing rookie ball in Arizona and learning from older mentors. Now, he’s ready to take on spring training less than a year after the Chicago Cubs took him in the fourth round of the 2025 Major League Baseball draft.
It should go without saying, but even the lowest level of professional baseball is massively different from high school ball. Kaleb Wing can attest to that.
Just four days after the Chicago Cubs selected him in the fourth round of the 2025 Major League Baseball draft out of Scotts Valley High School in July, the right-handed pitcher was in Mesa, Arizona, ready for rookie ball — a stop that many players fresh out of high school hit to prepare for a full minor league season.
“Those first couple days were just getting baselines of pretty much every metric you can think of,” said Wing, who turns 19 on Jan. 12. “Body weight, height, mobility, a bunch of medical imaging.”
Wing, primarily a shortstop for most of his playing career, started taking pitching seriously only a year before he was drafted. Despite his obvious natural talent, he said he spent the first few months with the Cubs in meetings about weightlifting, conditioning and nutrition. In fact, Wing said he didn’t throw at all for the six months in rookie ball, because he was focused on getting bigger and stronger and on preparing for his first full season in 2026.
“It was like here’s where you are now, and here’s where we need you to be, and this is what getting there is going to look like,” he said. “It was very detailed, but very exciting.”
Wing said that planning is one of the biggest differences in pro baseball. Every player has a routine and an individualized plan catered to his strengths and weaknesses — even the established professional players more than 10 years older than him. Having those veterans around provided him with some mentorship, too. He said he got the chance to pick the brains of guys who had already reached the majors, including 2021 11th-rounder Jack Neely and even 2023 All-Star Justin Steele, who finished fifth in the voting that year for the National League’s Cy Young Award recognizing the league’s best pitcher. But advice came from players of all calibers and stages of their careers.
“Right after the draft a couple guys got released and one of them sat me down to tell me don’t take any day for granted,” Wing said. “You’re working every day to be a big leaguer and don’t let a single day slip away from you.”
The everyday training tools at the team’s disposal are “unbelievable,” according to Wing. He described a small motion-tracking sensor manufactured by a company called Catapult that helps keep him on a steady routine each day. The device tracks the intensity of his motion and other training to ensure he’s working at a low intensity on some days and a high intensity on others. It might sound like something from MLB’s own surveillance state, but Wing takes the monitoring in stride.
“It’s just another way to keep guys healthier and monitor the intent of your movements,” he said. “It’s a crazy piece of technology that I’ve never seen before.”
In high school, Wing’s arsenal included a fastball that touched the mid-90s, a curveball, a slider and a changeup. That pitch mix is still intact, with no additions or subtractions at this point, but Cubs pitching coaches say adding velocity should be his main goal.
“I’ve had the number 100 [mph] in my head, so that’s been the goal,” he said. “I have a lot of work to do, and that’s been my daily reminder. I’m doing this to eventually get there.”
Wing expects to report to spring training in February and join the Cubs’ Single-A affiliate, the Myrtle Beach Pelicans in South Carolina, afterward. And while he works through his first full season in the minors, he has another big, but important, goal on top of getting stronger and maybe even reaching 100 on the radar gun: staying healthy.
“There’s more than 100 games in a minor league season and staying healthy through that is big,” Wing said, especially since that’s a far longer season than he’s played up to this point. “I have a long way to go to be where I want to be, so I’m working every day to put myself in a good position for it.”
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