



SCOTTS VALLEY >> Professional baseball’s hype machine works in ways more mysterious than a David Copperfield routine, and more quickly than a Aroldis Chapman fastball.
Last summer, Scotts Valley High’s soon-to-be senior Kaleb Wing was a relatively unknown infielder trying out for a spot in the prestigious Area Code Games showcase.
Eleven months later, the 6-foot-2, 180-pound shortstop is one of the most coveted players in the land — as a right-handed pitcher.
When MLB.com recently released its initial prospect rankings for the 2025 draft, which includes the best of the best in high school and college, a few months ago, Wing checked in at No. 82 overall. He currently sits at No. 87, days ahead of baseball’s annual two-day draft, which begins Sunday.
“My goal was to play the game a long time,” said Wing, of his childhood dream. “And I fall more and more in love with it every time I’m out there. It’s definitely cool, something I’ve always dreamed about. And I’m honored that people are taking notice of the hard work I put into it.”
Wing is projected to be selected some time in the third round, which could earn him a near seven-digit payday. He’ll earn more if he goes ahead of his projected selected spot and less if his stock drops between now and the draft.
Either way, Wing, whose father, Ryan, was a second-round draft pick in 2001 and pitched in the minor leagues for seven seasons, is going to have a decision to make: sign a pro contract and forego his collegiate career, or honor his commitment to the Loyola Marymount University and get a taste of the college experience.
A split-second decision put Wing in this current, cherished situation. During his Area Code tryout last June, the middle infielder was asked if he wanted to pitch during his audition. Having made a measly nine mound appearances in his life, Wing decided to, well, wing it. “Sure,” he said, on a whim.
He threw two types of pitches at the tryout, a fastball clocked in the high 80s and a makeshift curveball. Team coaches saw Wing’s promise. He not only made the Oakland A’s roster, he pitched again in week-long showcase in August, played out in front of hundreds of professional scouts and college coaches.
It was then, 11 months ago, when Wing had the same thought as the pro scouts. Mmm, I think we’ve got something here.
Wing met with his trainer, Matt Rossignol, a former independent league pitcher who owns Rossy’s Training in Scotts Valley, and the two devised a plan to make Wing a two-position talent. Not only would Wing add strength, he’d work on his pitching mechanics and build an arsenal that would further justify the interest he was generating.
When the high school season began in late February, so did the circus. Wing was no longer an unknown. Nor was he the same guy who took mound during Area Code tryouts.
When Wing first started pitching, his top fastball velocity was in the 88-90 mph range. In a short stretch, he’s now touching 96.
“There’s a lot of potential on the mound,” said Matt Rossignol, his trainer at Rossy’s Training. “He’s so new to it. He just started pitching less than a year ago. It has been a fun progression to watch him develop and see how far he’s come.”
Scouts, as many as 20 to 30 a game, showed up en force each Tuesday, eager to learn more about this blossoming talent with a young, fresh, and live arm.
Wing didn’t disappoint. He was considerably more polished and he doubled his arsenal. (He added a slider and changeup.) His fastball velo is big league ready. It has been clocked in the mid-90s.
“He’s been pretty incredible,” Falcons head coach Kevin Taylor said. “Imagine the pressure on a kid that age. The way he’s been able to handle it has been pretty incredible. They’re (scouts) even watching when he’s out stretching on the grass. He’s built for the moment. The kid has a great head on his shoulders.”
Wing was named the Santa Cruz Coast Athletic League’s Pitcher of the Year after helping the Falcons (12-16, 8-7) finish in third place and advance to the Central Coast Section playoffs. Wing (3-3) posted a 1.23 ERA over 45 2/3 innings on the season. He gave up 23 hits, 15 walks, and eight earned runs while striking out 79 batters.
Cruz said he wasn’t trying to strike out everyone he faced.
“I try to pitch to soft contact,” Wing said. “That’s when most punchouts come.”
Wing’s father has been an incredible resource. Ryan has helped him learn the intricacies of the game. On the mound, that means how to attack hitters.
Ryan served as the Falcons’ pitching coach and called pitches. Sometimes, his son would shake off his suggestions.
“It would get difficult sometimes,” Wing said. “When I do (shake him off), I better expect to talk through why I would. This is the first time I’ve done it and he’s done it years and years.”
In mid-June, Wing participated in the MLB Draft Combine at Chase Field in Phoenix.
He’s currently competing for the Corvallis Knights in the West Coast League. He was roughed up in his first two outings, but continues to learn with each appearance on the mound.
Wing isn’t concerned about where he gets chosen in the draft. He expects a lot from himself, and his primary goal is continuing to improve in every aspect of the game.
Written in Sharpie on his pitching glove is one of his goals: “100,” as in throw 100 mph.
“Sometimes velocity is good,” he said. “It can always get better. I’d like to see my velo increase more. There are guys that throw 106. I don’t see why not. That would be a pretty cool feat.”
Given his rate of improvement, no one is questioning him reaching that goal. The big question: Does he reach it as a college player or in the professional ranks?