5 questions Red Sox face this offseason

October 25th, 2023

This story was excerpted from Ian Browne's Red Sox Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

Five questions facing the Red Sox this offseason:

How sudden an impact can Breslow make?
The Red Sox landed their new leader of the front office, securing an agreement with Craig Breslow on Tuesday night, sources told MLB.com. The club has not confirmed the hiring of Breslow, which was first reported by The Boston Globe’s Alex Speier.

Now, all eyes will be on Breslow as he tries to lead the Red Sox back to contention. Breslow knows the market well, having pitched for the Red Sox in 2006, and again from ’12-15. Breslow’s success in the Cubs’ front office was well-chronicled, as he helped rebuild the team’s pitching department from the ground up.

But being a lead baseball executive is a different animal, and the Red Sox are confident the 43-year-old Breslow can hit the ground running. It will be interesting to see what kind of payroll Breslow has to work with. The Red Sox weren’t as aggressive in free agency during Chaim Bloom’s four years running the club as they had been in previous regimes.

Can they land Ohtani?
Not only have the Red Sox lacked success the last two seasons, but there’s also been a lack of buzz around the club. Nothing could reverse both trends faster than the addition of the game-changing Shohei Ohtani. The Red Sox are one of probably just a handful of franchises that have the financial resources to land a player of Ohtani’s astounding skillset. It’s true that Ohtani won’t be able to pitch in 2024 as he recovers from Tommy John surgery. But his bat would be enough of a weapon to tide the Red Sox and their fans over until he can enter the rotation in ’25.

Who will join the rotation?
It wasn’t a second guess from media and fans that the Red Sox didn’t have enough quality starting pitching depth for 2023. It was, in fact, a first guess. And it turns out the skepticism was right. While Chris Sale had some nice moments when he was healthy last year, he shouldn’t be counted on as a top-of-the-rotation starter at this point in his career. Brayan Bello stood in as the ace and played the part well at times, but he’s better suited to be a No. 3 starter at this stage. The Red Sox need to be aggressive in their pursuit of rotation additions this winter, be it on the free-agent market or via trades. Aaron Nola, Jordan Montgomery, Blake Snell and Sonny Gray are among the top free-agent starters who could entice the Sox.

What to do with Verdugo?
Alex Verdugo, a Gold Glove finalist in right field, is headed into his final arbitration-eligible season in Boston. The left-handed hitter has had his ups and downs in his four years in Boston and got benched twice in ’23 for disciplinary reasons. The Sox have three other left-handed-hitting outfielders in Masataka Yoshida, Jarren Duran and Wilyer Abreu, the latter of whom impressed following his callup in late August. If the Sox don’t view Verdugo as someone they are comfortable signing to an extension, they’d be best off trading him to save some money that can be allocated to the pitching staff. They might also be able to get some pitching in a Verdugo trade.

Will Turner come back?
Of all the moves the Red Sox made last offseason, the one that worked out the best was the signing of veteran Justin Turner. The right-handed hitter, in his age-38 season, notched a career-high of 96 RBIs. Turner gained immediate comfort at Fenway and was one of the best situational hitters in the league, consistently driving in that run from third with less than two outs. Turner has a player option that he is all but certain to decline so he can test the free-agent market. One of the tricky things about bringing Turner back is that the Red Sox need to find a way to get better defensively. Part of that solution could be putting someone like Yoshida at DH, which is where Turner got most of his playing time last season. And of course, if the Red Sox do get Ohtani, that would all but close the book on Turner coming back.