Scouting Report

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Scouting grades: Fastball: 65 | Curveball: 60 | Slider: 60 | Cutter: 60 | Changeup: 45 | Control: 50 | Overall: 55

Scouts have followed the Witherspoon twins since high school, with the Diamondbacks trying to sign Malachi to an over-slot bonus as a 12th-rounder in 2022. Though they have similar stuff, Kyson since has surpassed him as a prospect after performing significantly better in their time at Northwest Florida State JC and Oklahoma. He has much more of a starter look and should be the first college right-hander drafted in 2025.

Witherspoon has swing-and-miss stuff, starting with a mid-90s fastball that peaks at 99 mph and stands out more for its power than its modest life. His mid-80s slider can touch 91 mph while featuring both horizontal action and depth, and he'll turn it into an upper-80s cutter that he uses just as often. He's showing more consistency with his low-80s downer curveball, giving him another plus offering, while his upper-80s changeup is a work in progress that gets too firm but will show interesting fade at times.

Witherspoon uses a compact arm action to generate quality stuff with little effort. His athleticism and mechanics have translated into improved control and command this spring, and better location has made it easier for him to get hitters to chase outside of the strike zone. He has all of the ingredients to become a frontline starter.

Video scouting report »

Scouting grades: Fastball: 60 | Curveball: 55 | Slider: 50 | Cutter: 55 | Changeup: 45 | Control: 50 | Overall: 50

The Witherspoon twins began attracting attention as Florida high schoolers, with the Diamondbacks making a run at signing Malachi for an over-slot bonus as a 12th-rounder in 2022. Kyson surpassed his brother as a prospect after outperforming him in three college seasons together at Northwest Florida State JC and Oklahoma. After he topped the Southeastern Conference with a 5.4 K/BB ratio last spring, he unexpectedly lasted 15 picks in the Draft before the Red Sox gladly signed him for $5 million. His pro debut with High-A Greenville was a bit uneven, but his arm talent was enough for the Orioles to make sure he was included in the package they got in return for Adley Rutschman at the Trade Deadline.

Witherspoon has gotten chases and missed bats with all five of his pitches in the past, the best of which is a mid-90s fastball that has topped out at 97-98 mph this season and compensates for relatively modest life with plenty of deception. His top secondary offering is an upper-80s cutter that reaches 92 mph, with his tight mid-80s slider and big-breaking upper-70s curveball close behind. He doesn't have the same trust and consistency with his upper-80s changeup, which is too firm but flashes interesting fade.

If Witherspoon can do a better job of commanding his slider and landing his curveball in the zone, he could have four plus offerings. He has a compact arm action that produces quality stuff with little effort and makes it difficult for hitters to pick up his pitches. His athleticism translated into more consistent mechanics and location during his junior year with the Sooners, giving him the look of a frontline starter if he can rediscover what worked for him while he was with the Sooners.

Scouting grades: Fastball: 65 | Curveball: 60 | Slider: 60 | Cutter: 60 | Changeup: 45 | Control: 50 | Overall: 55

Scouts started following the Witherspoon twins when they were Florida high schoolers, with the Diamondbacks trying to sign Malachi to an over-slot bonus as a 12th-rounder in 2022. Kyson surpassed his brother as a prospect after performing better in their three seasons together at Northwest Florida State JC and Oklahoma. After he led the Southeastern Conference in K/BB ratio (5.4) this spring, the Red Sox were delighted to find him available with the 15th overall pick and signed him for $5 million.

Witherspoon has swing-and-miss stuff, starting with a mid-90s fastball that peaks at 99 mph and stands out more for its power than its modest life. His mid-80s slider can touch 91 mph while featuring both horizontal action and depth, and he'll turn it into an upper-80s cutter that he uses just as often. He's showing more consistency with his low-80s downer curveball, giving him another plus offering, while his upper-80s changeup is a work in progress that gets too firm but will show interesting fade at times.

Witherspoon uses a compact arm action to generate quality stuff with little effort. His athleticism and mechanics have translated into improved control and command this spring, and better location has made it easier for him to get hitters to chase outside of the strike zone. He has all of the ingredients to become a frontline starter.

Transactions

Team	Date	Transaction
	08/26/2026	Frederick Keys placed RHP Kyson Witherspoon on the 7-day injured list.
	08/04/2026	Frederick Keys activated RHP Kyson Witherspoon.
	08/03/2026	Baltimore Orioles traded C Adley Rutschman, C Jake Rogers and cash to Boston Red Sox for RHP Kyson Witherspoon, CF Enddy Azocar, C Carlos Narváez, RHP Anthony Eyanson and Player To Be Named Later.
	08/03/2026	RHP Kyson Witherspoon assigned to Frederick Keys.
	04/01/2026	RHP Kyson Witherspoon assigned to Greenville Drive from FCL Red Sox.
	03/05/2026	RHP Kyson Witherspoon assigned to Boston Red Sox Prospects.
	08/11/2025	RHP Kyson Witherspoon assigned to FCL Red Sox.
	07/20/2025	Boston Red Sox signed RHP Kyson Witherspoon.
	06/03/2025	RHP Kyson Witherspoon assigned to College Workout.
	01/31/2025	RHP Kyson Witherspoon assigned to Oklahoma Sooners.
	04/02/2024	RHP Kyson Witherspoon assigned to Chatham Anglers.
	04/02/2024	Chatham Anglers activated RHP Kyson Witherspoon.
	02/06/2024	Oklahoma Sooners activated RHP Kyson Witherspoon.
	02/06/2024	RHP Kyson Witherspoon assigned to Oklahoma Sooners.
	05/09/2023	RHP Kyson Witherspoon and assigned to College Workout.
	06/01/2022	SS Kyson Witherspoon and assigned to High School Workout.