Inside The Red Sox

Red Sox 21-Year-Old Could Be Fast-Tracked To Big Leagues: Insider

How will the Sox handle Kyson Witherspoon?
May 10, 2025; Kansas City, Missouri, USA;  A general view of a Boston Red Sox's cap and glove on the field before a game against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: Peter Aiken-Imagn Images
May 10, 2025; Kansas City, Missouri, USA; A general view of a Boston Red Sox's cap and glove on the field before a game against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: Peter Aiken-Imagn Images | Peter Aiken-Imagn Images

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The Boston Red Sox's pitching development program has grown leaps and bounds under chief baseball officer Craig Breslow.

A year after all the prospect storylines were being dominated by position players like Roman Anthony and Kristian Campbell, it's the pitchers who have seized the spotlight. From Payton Tolle's fast promotion to Connelly Early's early success, young Red Sox pitchers have become the strength of the farm system.

Is it possible, though, that the pitcher who will make the largest impact on the team's future has yet to make his professional debut? Kyson Witherspoon, the club's 2025 first-round pick, could reportedly be headed for a lightning-fast minor-league experience.

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Red Sox insider says Witherspoon could start in Double-A

On Monday, Alex Speier of the Boston Globe floated the idea of Witherspoon starting next season in Double-A, putting him within a stone's throw of Boston and making a 2026 debut entirely possible, if not expected.

"Witherspoon, a first-round selection this year, is considerably more advanced entering pro ball than was Tolle, with a more far-reaching mix of pitches along with more power to his arsenal," wrote Speier. "As a result, it’s at least within the realm of possibility he could open the year in Double A (Tolle was in High A to start 2025), with a real possibility of zooming to the big leagues."

Witherspoon features an arsenal with four pitches that MLB Pipeline currently grades at a 60 level or better (fastball, slider, curveball, cutter). He struck out 124 batters in only 95 innings in the Big 12 this season, pitching to a 2.65 ERA for the Sooners. Whether he starts at High-A or Double-A, the Red Sox will look for him to maintain a similar strikeout rate, which was Tolle's calling card this year.

The Red Sox would love a righty to emerge from the farm system as the future co-ace of the rotation alongside lefty Garrett Crochet. Witherspoon won't likely take up that mantle by September, but he certainly could emerge as the leader in the clubhouse.

More MLB: Red Sox Insider Identifies 3 Likely Free-Agent Pitching Targets For Boston


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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org