Boston Red Sox

Why Payton Tolle is already being compared to a Red Sox World Series winner

The 2024 second-round pick is reportedly set to make his MLB debut.

Payton Tolle Red Sox
Payton Tolle pitching for the Greenville Drive. Gwinn Davis /Greenville Drive

Payton Tolle draws an impressive comparison: A little over a year after the Red Sox selected left-hander Payton Tolle in the second round of the MLB Draft (50th overall), the 22-year-old is reportedly set to make his big league debut.

According to MLB reporter Ken Rosenthal of The Athletic, Tolle is “expected” to make his first career start for the Red Sox at Fenway Park on Friday against Paul Skenes and the Pittsburgh Pirates.

As Rosenthal noted, it’s a “meteoric rise” for the talented youngster. Tolle has a combined 3.04 ERA with 133 strikeouts in 91.2 innings pitched across three levels of Boston’s minor league system in 2025.

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Tolle stands at 6-foot-6, and has touched 98.6 mph with his fastball. Given his projected potential and ability, it’s natural that he’s invited comparison to a previous Red Sox-drafted left-handed starter: Jon Lester, who helped Boston win two World Series (and added another in Chicago with the Cubs).

“The Red Sox are calling up their most exciting homegrown left-handed pitcher since Jon Lester,” noted MLB.com’s Sam Dykstra in a scouting report of Tolle.

Like Tolle, Lester was a hard-throwing lefty (standing at 6-foot-4) that the Red Sox drafted in the second round (back in 2002). And while there are certainly some clear differences — Lester was drafted as an 18-year-old vs. Tolle at 22, and the former also spent four seasons in the minors — Dykstra isn’t the only one to have made the comparison.

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“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,” Portland Sea Dogs manager Chad Epperson recently told Alex Speier of The Boston Globe.

“He just wants information,” Epperson added. “He wants to be around this. And I think those intangibles there, and with the talent, this guy’s going to be really, really special.”

Of course, dominating at the Double A level is different than facing Major League batters, as Tolle will undoubtedly learn. Still, Epperson — as an extension of the Red Sox organization — seems to be fully cognizant of this fact.

“Do I think he’s going to be a dominant big league pitcher? Absolutely,” Epperson told Speier. “Can I say that the first month of his career in the big leagues? No, but I can tell you that nothing’s going to change with his mind-set, and that makes me very comfortable saying I think this guy is going to help our club, and I think he could help it really soon.”

Scores and schedules:

The Red Sox completed the four-game sweep of the Orioles with a 3-2 win on Thursday.

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Tonight, Boston begins a three-game set against the Pirates at Fenway Park. First pitch is set for 7:10 p.m., with rookie left-hander Payton Tolle reportedly set to make his MLB debut against Pittsburgh ace Paul Skenes.

On Saturday, Boston College begins its football season at home against Fordham at 2 p.m.

Also on Saturday, the Revolution host Charlotte FC in a crucial matchup that will kick off a little after 7:30 p.m.

More from Boston.com:

Story time: Red Sox shortstop Trevor Story acrobatically turned a double play in Thursday’s win.

On this day: In 2000, the Red Sox routed the Devil Rays 8-0 in a wild game, with Pedro Martinez taking a no-hitter into the 9th inning after eight Tampa players and coaches were ejected in the fallout to a 1st inning brawl.

The incident occurred after Martinez hit Devil Rays leadoff batter Gerald Williams. Williams proceeded to charge the mound before being tackled, causing the benches-clearing brawl.

Boston outfielder Carl Everett went 4-for-5 with two home runs and six RBIs, finishing the game a single away from a cycle. Martinez finally yielded a single to Devil Rays catcher John Flaherty with no outs in the 9th, but totaled 13 strikeouts in a signature performance.

Pedro Martinez 2000 Rays

Daily highlight: Here’s a well executed fake punt touchdown from South Florida to take you into the weekend.

Hayden Bird

Sports Staff

Hayden Bird is a sports staff writer for Boston.com, where he has worked since 2016. He covers all things sports in New England.

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