Aug 29, 2025; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Payton Tolle (70) pitches against the Pittsburgh Pirates during the first inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images Eric Canha-Imagn Images

Payton Tolle’s Breakout Sparks Comparisons to Red Sox Legend

Originally posted on Boston Red Sox on SI
By Patrick McAvoy | Last updated Feb 24, 2026 11:07 AM ET

It's hard not to be excited about the top pitching prospects in the Boston Red Sox's farm system right now.

Boston has quickly gone from being a team that struggled to develop pitching talent to seemingly a pitching factory in a short time. To put it into perspective, in 2023, two of Boston's top 10 prospects were pitchers in Bryan Mata at No. 7 and Brandon Walter at No. 8. Fast forward to now, and six of Boston's top 10 prospects are pitchers with Payton Tolle at No. 2, Kyson Witherspoon at No. 3, Connelly Early at No. 4, Jake Bennett at No. 7, Marcus Phillips at No. 9 and Anthony Eyanson at No. 10. Times certainly have changed.

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Tolle and Early both had a cup of coffee in the big leagues in 2025 as well. Both are fighting for the No. 5 spot in the club's rotation along with guys like Kutter Crawford, Patrick Sandoval and Johan Oviedo. While they may not be with the club on Opening Day, the future is bright. One thing that stands out about Tolle specifically is that while scouting each team in the American League East's top prospects, Baseball America quoted Double-A manager Chad Epperson comparing Tolle to Jon Lester.

Payton Tolle has some high expectations

"Payton Tolle, LHP, Red Sox," the unnamed Baseball America staff wrote. "Scouting Report: While Tolle wore a jet pack in his 2025 ascent, he’ll likely open 2026 in the Triple-A rotation to better define and refine his secondary mix. His double-plus fastball gives him an obvious late-innings floor, but the immense developmental strides he made in 2025 suggest a midrotation—or better—ceiling. 'This is hard for me to say, but this guy, he’s a Jonny Lester-type guy to me—can’t-miss, dominant, big leaguer,' Double-A Portland manager Chad Epperson said. 'This guy’s going to be really, really special.'"

Lester was a beloved figure in Boston. He was a five-time All-Star, three-time World Series champion and 200-game winner throughout his 16-year big league career. If Tolle can end up being anything like Lester, Boston is going to be alright in the rotation for a long time to come.

Boston is loaded with pitching now and for the future. It's hard not to be excited.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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