Scouting Report

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Scouting grades: Fastball: 55 | Curveball: 55 | Changeup: 45 | Control: 50 | Overall: 45

Back in 2001, Ryan Wing was a second-round pick of the Chicago White Sox out of Riverside City College, a two-year school outside of Los Angeles. The left-handed pitcher spent seven seasons in pro ball, topping out at the Triple-A level in the A’s organization. Now it’s his son Kaleb’s turn as a two-way player from the northern California high school ranks, a defensive-minded shortstop who appeared to be turning a corner this spring as a right-hander with an uptick in stuff, allowing him to move up boards.

Wing doesn’t have a ton of history on the mound, but appeared to be figuring things out in a hurry during his senior season. The athletic 6-foot-2 righty made the Area Code Games as a backup arm and was mostly around 88-90 mph with a big loopy overhand curve. This spring he came out of the gate showing a fastball up to 95 mph and hasn’t backed off from those gains. His curve now flashes plus as a power breaker with depth, and his changeup is developing into a solid third offering.

Wing’s athleticism helps him repeat his delivery and find the strike zone consistently. There’s a little concern about how much strength he’ll be able to add to his narrow frame, but the uptick in stuff across the board could have teams interested in signing him away from his commitment to Loyola Marymount, where he had originally planned to both pitch and hit.

Scouting grades: Fastball: 55 | Curveball: 55 | Changeup: 50 | Control: 50 | Overall: 45

The son of White Sox 2001 second-round pick Ryan Wing, who reached Triple-A, Kaleb appeared headed to Loyola Marymount as an athletic shortstop/right-hander. Then his stuff made a jump during his 2025 senior season and he became the best pitching prospect to come out of Scotts Valley (Calif.) HS since Robbie Erlin was a Rangers third-rounder in 2009. The Cubs popped Wing in the fourth round and paid him $1.5 million, more than double slot value.

After working at 88-90 mph with his fastball at the Area Code Games the previous summer, Wing operated at 90-96 with high spin rates and good carry and armside run on his heater this spring. He also tightened up his curveball, which showed flashes of becoming a plus pitch with upper-70s velocity and downer break. He also has the makings of a useful low-80s changeup with similar action.

Extremely athletic for his position, Wing gets down the mound well and creates plenty of extension in his delivery. He repeats his delivery well and has no problem providing strikes. He needs to add strength to answer questions about his durability but comes with the upside of a mid-rotation starter.

Transactions

Team	Date	Transaction
	08/04/2025	ACL Cubs activated RHP Kaleb Wing.
	07/25/2025	RHP Kaleb Wing assigned to ACL Cubs.
	07/24/2025	Chicago Cubs signed RHP Kaleb Wing.
	05/23/2025	RHP Kaleb Wing assigned to College Workout.