The Red Sox may not get the luxury of waiting around this offseason. With the General Manager Meetings running from November 9 through November 12 in Las Vegas, Nevada, the market could move fast, and the looming lockout on December 1 only raises the pressure. That means Craig Breslow has to be ready to act early if Boston wants to make real progress before the winter really kicks in.
One obvious target sits in the outfield: Randy Arozarena. He looks like a strong fit for Boston because he’d bring power, right-handed balance and more speed on the bases to the lineup.
The 31-year-old left fielder has posted six straight 20-20 seasons, and that kind of production is hard to ignore. He’s also expected to draw interest from big-market teams along the East Coast, plus the Chicago Cubs, and he’s a Scott Boras client, which means the price won’t be cheap.
Spotrac projects a four-year, $81 million deal, but the Red Sox may need to go a little higher - four years and $92 million - if they want to get Arozarena to decide quickly and land in Boston.
Boston also needs help in the rotation, especially from the right side, and Sonny Gray has emerged as a realistic answer. What once looked like a long shot now appears more possible, with Gray open to a return.
He’s the cleaner fit for Boston than some of the other names out there because he’s already shown he can handle the job in Boston and is likely to finish top five in AL Cy Young voting. Just as important, he should come at a shorter term, which matters with Garrett Crochet and Ranger Suarez already attached to long-term big-money deals and a possible eventual extension for Payton Tolle still on the table.
The alternatives come with baggage. Michael King drew plenty of attention for his two-inning save in Game 3 of the NLDS while filling in for Mason Miller, who missed the game because of the birth of his child, but he also carries injury concerns.
Add in a declining strikeout rate and some ugly underlying numbers - 4.13 FIP, 4.33 xFIP and 4.40 xERA - and there’s real risk there. Freddy Peralta has been excellent with the Rays, but that can’t erase how rough he was with the Mets.
A deal for Gray could be structured in a way that gives both sides flexibility. If the Red Sox and Gray agreed to a mutual option, he’d make $30 million in 2027.
Instead, Breslow could offer a one-year, $25 million contract with a player option for another $20 million in 2028 if Gray wants to keep going. That would give Gray control over his future while potentially saving Boston a little money if he only stays for one season.
If Arozarena comes in, the next move becomes even clearer: trade Jarren Duran for whatever return Boston can get. The problem is that Duran’s value is at a low point, which makes it hard to expect much of a haul. Still, the San Diego Padres have long liked him and remain interested, and there could be other teams involved as well.
Timing matters here, too. The non-tender deadline is November 20, so if Duran isn’t dealt before then, the Red Sox are likely to cut ties and move on with Arozarena on the roster.
Boston can still use that deadline to squeeze out a better offer by reminding interested clubs that not tendering Duran would make him a free agent who could sign anywhere. If a team wants him, it has to convince the Red Sox that its package is better than simply waiting a few weeks and letting him go.
In Other News...
Red Sox Early Returns On Breslow Extensions Are Hard To Ignore
Since Craig Breslow took over as chief baseball officer, the Red Sox have made a clear habit of locking up young talent early, and the list is already a notable one. Garrett Crochet, Roman Anthony, Kristian Campbell, Ceddanne Rafaela and Brayan Bello have all been extended, giving Boston a mix of cost certainty and long-term control as it tries to build around a younger core.
The early returns, though, are not all pointing in the same direction. Some of those deals already look like smart business, while others have been harder to judge, especially with Kristian Campbell fading after a strong start and Brayan Bello still searching for steadier results on the mound. For a front office trying to balance upside, payroll and patience, the rankings of these extensions say as much about the Red Soxs future as they do about the present. [Read more 🡒]
Red Sox Front Office Just Took Another Hit Craig Breslow Cant Ignore
Taylor Smiths move out of Bostons orbit is another reminder that the Red Sox are not just trying to build a roster, they are trying to keep the right people in the front office. Smith, who previously worked for the Red Sox, has been named the next president of baseball operations for the Oakland Athletics, a promotion that underscores how valued he has become around the league.
Craig Breslow acknowledged the loss of talented personnel like Smith and pointed to the challenge of replacing key voices inside baseball operations. For a front office still shaping its identity, those departures matter because the work behind the scenes is every bit as important as the moves on the field, and Boston now has another important vacancy to address. [Read more 🡒]
Red Sox Rotation Puzzle Just Got More Complicated For 2027
The Red Sox have spent plenty of time building toward a rotation that looks sturdy on paper for 2027, with Garrett Crochet, Ranger Suarez, Payton Tolle, Jake Bennett and Brayan Bello forming an intriguing mix of power, experience and upside. But even with that group in place, the picture is not fully settled, especially with Sonny Gray now looming as a free agent and no guarantee he returns to Boston.
If Gray departs, the front office could look outside the organization for another proven arm, and Chicago Cubs All-Star Shota Imanaga is the kind of name that naturally fits the conversation. The fit is not as simple as it sounds, though, because Imanaga would add another left-hander to a rotation that already has several of them, which means any pursuit would likely come with some roster math and a tough decision or two. [Read more 🡒]