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Craig Breslow maps out Red Sox’ top priority at trade deadline, contract talks with Bregman
"We have some depth, but I think if there’s the opportunity to provide some impact starting pitching, and add that to the group, that’s probably where we’d focus.”
As uneven as the Red Sox’s 2025 season has been so far, Alex Cora and his group are seemingly back in the playoff picture.
After posting six straight wins against two cellar-dwellers in the Nationals and Rockies, Boston is tied with the Mariners for the third and final wild card spot entering Thursday night against the Rays.
Sitting now at four games over .500, the Red Sox still have plenty of work to do when it comes to leapfrogging teams in the AL, with FanGraphs tabbing Boston with just a 35.9 percent chance of making the playoffs.
But, with the Red Sox gaining some momentum and MLB’s July 31 trade deadline readily approaching, what will chief baseball officer Craig Breslow do to augment Boston’s roster?
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For now, it looks as though all options are on the table.
“It kinda depends on where we are, so we have to zoom out a little bit and try to figure out who we are, what do we have coming back and what do we think is sustainable, Breslow said during his appearance on WEEI’s “The Greg Hill Show” on Thursday.
Boston’s perceived weaknesses could change rapidly, Breslow said, citing that starting pitching was viewed as the team’s Achilles heel for most of the spring.
“A month and a half ago, we would have talked a ton about starting pitching and getting more consistency and finding someone who slots in toward the top of the rotation behind Garrett [Crochet],” Breslow said. “And then you look at what Lucas [Giolito] and Brayan [Bello] have done over the last month and a half, and you start to feel confident in the way the starting pitching is coming together.”
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Both Giolito and Bello have played key roles in Boston’s recent upswing over the last month — looking more and more like legitimate weapons in the rotation behind Crochet (9-4, 2.39 ERA).
Bello is 3-2 with a 2.83 ERA over his last nine starts, while Giolito is 5-0 with a miniscule 0.70 ERA over his last six outings, lowering his ERA from 6.42 to 3.36 over that stretch.
But, even with Giolito and Bello settling into grooves this season, Breslow stressed that pitching still remains a focus for a team whose starters have a 4.18 ERA this year.
“That said, you can never have too much [starting pitching] so I think that’s probably what we would prioritize. But we’ve seen what [Richard] Fitts has done, [Hunter] Dobbins is getting healthy, [Tanner] Houck is getting healthy. We have some depth, but I think if there’s the opportunity to provide some impact starting pitching, and add that to the group, that’s probably where we’d focus.”
Adding another proven starter who could slot behind Crochet would create a positive domino effect for the rest of Boston’s rotation, especially given the underwhelming returns put forward by other arms like Walker Buehler and Tanner Houck.
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With a few weeks remaining before the trade deadline, MLB Network’s Jon Morosi reported on Wednesday that the Red Sox are “monitoring” the market on Twins righty Joe Ryan.
It would require a significant return to pry a pitcher with term (two more arbitration-eligible seasons in 2026 and 2027), but Ryan could be a missing piece for Boston as a dominant No. 2 starter.
Ryan has been one of the best pitchers in baseball during the 2025 season, posting an 8-4 record with a 2.76 ERA, 0.89 WHIP, and 116 strikeouts over 104.1 innings pitched.
As the Red Sox assess their options at the deadline and decide whether or not they want to buy, they must also weigh what their next steps are with Alex Bregman.
Despite missing six weeks of action due to a quad strain, Bregman has provided plenty of value to Boston after signing with the team in February, earning an All-Star nod in just 51 games with the franchise.
The 31-year-old veteran did sign a three-year, $120 million contract with Boston this spring, but Bregman does have the option to opt out and test free agency once again after both this season and next year if he believes he can secure himself a larger, long-term deal.
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With the Red Sox dealing away Rafael Devers last month, retaining Bregman on a long-term extension would seemingly stand as a good bit of business by Breslow and Boston as they try to build a foundation moving forward.
“I think ‘ongoing’ is always a fair summary, given this is something on our mind and it’s something on Alex’s mind,” Breslow said of contract talks with Bregman, focusing more on Bregman’s expected return to the field this weekend against the Rays.
“I’ve been pretty outspoken about what he’s provided on the field and in the clubhouse,” Breslow added. “He’s a guy we would like to have here in a Red Sox uniform for a long time.”
Speaking last month, Bregman shared a similar sentiment about wanting to stay with Boston on a long-term basis.
“I expected to love playing here and I have definitely loved playing here,” Bregman said of playing in Boston on June 30, per MassLive’s Chris Cotillo. “It’s a great place to play baseball. Being able to play for this organization is awesome.
“My expectations were all very positive and it’s definitely lived up to those positive expectations.”
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