Inside The Red Sox

Red Sox Must Avoid This Payton Tolle 'Mistake,' Says Ex-MLB GM

Tolle has become the biggest x-factor in the pennant race
WooSox pitcher Payton Tolle gets ready to throw a pitch during his first Triple-A start on Aug. 10, 2025 at Polar Park.
WooSox pitcher Payton Tolle gets ready to throw a pitch during his first Triple-A start on Aug. 10, 2025 at Polar Park. | WooSox Photo/Ashley Green / USA TODAY NETWORK via Imagn Images

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With only 28 games left in the regular season, the Boston Red Sox still have one massive question to answer.

Now that Walker Buehler is out of the rotation, which the team says is a permanent change for the rest of the year, Boston has an opening in the No. 5 slot in its rotation. Right now, it looks as though two Triple-A left-handers, Kyle Harrison and Payton Tolle, are the two top candidates to fill it.

Though Harrison came to Boston in a high-profile trade and has more experience, it's clearly Tolle who has the it-factor right now. He's been shooting up top prospect lists all year, and after three dominant starts at Triple-A, he could find himself in the majors at the end of his first season in professional baseball.

Will Tolle debut this season? If so, there's still another question to address: put him in the rotation, or use him out of the bullpen?

Red Sox urged not to use Tolle out of bullpen

On the most recent episode of the "Baseball Isn't Boring" podcast, former Toronto Blue Jays general manager and Massachusetts native J.P. Ricciardi, who sees a lot of Boston's Triple-A team in Worcester, urged the Red Sox to keep Tolle out of the bullpen and put him in the rotation at their earliest convenience.

"I think Tolle is definitely a starter, and I think they'll make a big mistake if they try to pitch him out of the (bullpen)," Ricciardi said. "I would try to pitch him right now, put him in the rotation. He could come up to the big leagues. He's the most big-league-ready guy that I've seen that they have down there.

"His fastball plays. He reminds me of David Wells. He's got that big David Wells body. He's athletic like David Wells was athletic. He's a former two-way guy, those guys always find a way to figure it out."

It's high praise, and Tolle has earned it. He's punched out an incredible 133 batters in just 91 2/3 innings of work across three levels of the minors, and held the Miami Marlins' Triple-A affiliate to just one hit with nine punchouts in his most recent outing.

Tolle is currently slated to pitch for the Worcester Red Sox on Friday. The Red Sox have yet to announce their starters for the weekend series against the Pittsburgh Pirates, but either Tolle or Harrison would be an option to pitch on both Friday and Saturday.

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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