Quick Take
Right-hander Kaleb Wing expects to report to rookie ball in Mesa, Arizona, within a week or so after being selected in the fourth round of the Major League Baseball draft. Having come from a family of ballplayers, he says that playing professionally has always been the dream.
Scotts Valley High School’s Kaleb Wing didn’t really pitch seriously until this past season as a senior, but it seems to have worked out just fine.
On Monday, Wing, 18, was selected by the Chicago Cubs in the fourth round of the 2025 Major League Baseball draft, becoming the 121st name off the board in this year’s draft. The 6-foot-2, 180-pound right-hander is forgoing his scholarship to play infield at Loyola Marymount University to start his journey in professional baseball.
He’s not even the first — or even second — member of his family to play professionally. His father, Ryan, was drafted in the second round by the Chicago White Sox in 2001, and pitched in the minor leagues for seven seasons. Before that, his grandfather Harry played for one season in the San Francisco Giants’ minor league system in 1979.
“I couldn’t be more excited for the opportunity,” Kaleb Wing told Lookout on Monday afternoon, adding that it’s an honor to follow in his father and grandfather’s footsteps. “My dream has always been to play professional baseball, and to see that come to reality has been something I would have never thought. It’s absolutely amazing.”
Despite being a shortstop for most of his playing career, it almost seems like destiny that Wing would end up a pitcher, as both his father and grandfather were pitchers, too. However, simply transitioning to a new position is a lot different than taking on the role and immediately winning 2025 Pitcher of the Year in the Santa Cruz Coast Athletic League, which is exactly what Wing did.
Wing said he tried out for the Area Code Games last year — one of the country’s premier showcases for high school baseball talent — and made the team as a pitcher, despite initially starting the tryout as a shortstop. However, Wing said pitching always appealed to him.
“I was always kind of undersized, so pitching was just put on the back burner,” he said. “I was given a couple opportunities to pitch at some big events, ended up turning a couple heads, and decided to take it pretty seriously.”
The Area Code Games were a big turning point, said Wing. He added that his trainer, Scotts Valley-based Matt Rossignol, played a big role in honing his mechanics and turning him into the successful pitcher he is now.
“I kept my head down and worked throughout the whole rest of the summer, fall, and spring,” he said. “I made some big gains between the Area Codes and now.”
As it stands, Wing has a fastball that touches the mid-90s, a curveball, a slider and a change-up. Scouts believe that his fastball and curveball are already very good pitches, while his changeup is quickly developing into another effective weapon — although Wing himself thinks it might already be his best pitch. He’ll take that arsenal with him to Mesa, Arizona, within the next week, where he’ll complete a physical and sign his contract to officially begin the next and biggest chapter of his baseball career to date. After that, he expects to hit the ground running and start his journey through the minor leagues in pursuit of the show.
Past teammates and friends say he deserves every bit of recognition he gets. Quinn Turowski, who graduated from Scotts Valley High in 2024 and lived just down the street from Wing, said the two of them would practice turning double plays when they both played middle infield.
“He’s a great infielder, but the arm was always there,” he said. “He just made that decision to focus on pitching, and that’s what MLB is looking for, someone throwing hard on the mound.”
Fellow Scotts Valley resident Brock Ketelsen agreed that Wing’s arm was always strong, and that his work ethic always stood out, especially before he hit his growth spurt: “He really had to hone his craft to be a good hitter, and he always worked so hard on his defense. Then he grew into his body, hopped on the mound for the first time, and it took off from there.”
Ketelsen said that he and Wing have been best friends since elementary school and share a “brotherly bond.” He said that Wing always pushed his teammates, including Ketelsen, to be the best versions of themselves on the field. As Ketelsen himself looks forward to playing baseball at Stanford University next year, he’ll hold that bond closely.
“He’s been devoted to his craft since Day 1. Before I even knew what really working hard was, he was always [at practice] early, putting in extra reps before and after, and he pushed me to be better myself,” he said. “That’s just the kind of person he is. He’s been a great friend and a great teammate, and to be a part of his journey has been amazing.”
As Wing prepares to officially play professional baseball, he’s staying locked in.
“Today is a special day, but there’s still a lot of work ahead of me,” he said. “This is the first step in the process, but I’ve got a long way to go to be where I want to be.”
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