Where Red Sox Stand on Extensions for Connelly Early, Payton Tolle

Extensions have been a theme of Craig Breslow's tenure of Boston Red Sox chief baseball officer.

In the past two years, Boston has locked up Brayan Bello, Ceddanne Rafaela, Garrett Crochet, Kristian Campbell, and Roman Anthony beyond arbitration, tying each of them to the Red Sox until at least 2029.

Coming into spring training this year, it was only natural that the prospect of more such extensions might be on the table. Rookie left-handed starting pitchers Connelly Early and Payton Tolle make the most sense as candidates.

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Who could Red Sox extend next?

Sep 21, 2025; Tampa, Florida, USA; Boston Red Sox starting pitcher Connelly Early (71) throws a pitch against the Tampa Bay Rays during the first inning at George M. Steinbrenner Field. Mandatory Credit: Dave Nelson-Imagn Images | Dave Nelson-Imagn Images

Breslow was asked about the potential for more extensions on Wednesday, and while he affirmed that the strategy was part of the Red Sox's toolbox, he understandably didn't single out any individuals who were on the radar.

“We’re always thinking about trying to identify those cornerstone pieces and preserve them for as long as possible,” Breslow said, per Chris Cotillo of MassLive. “We’ll see if anything is able to get over the line but it’s always something that’s part of our strategy for building a sustainable, winning organization.”

While Early and Tolle wouldn't necessarily have incentive to give away details of any conversations with the organization in a public forum, both made it seem as if those talks had not even begun at this point.

“I haven’t spoken at all about that,” Early said, per Cotillo. “I think it’s more that I have to be able to go out there and show what I can do for a longer amount of time before that’s even a consideration."

“Not that I know of," added Tolle, per Cotillo. "I’ve really enjoyed this organization and whatever happens, happens with it. I think that has to do with some higher powers that I try not to worry about. I’ve really enjoyed the Red Sox. Now being a part of this group has been very special to me.”

It's early in the spring, but the Red Sox also don't yet know if either Tolle or Early will open the season in the rotation. It's good to be proactive, and we won't dismiss the idea offhand, but it seems as though it would make sense to see more at the big-league level before inking another extension.

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