Emotions are running high after the Boston Red Sox’ embarrassing Wild Card Series loss to the New York Yankees.
Red Sox fans could only watch with disgust as the offense was outscored 18-2 in the two-game sweep. They were left scratching their heads after manager Chad Tracy’s questionable decisions to pull starters Payton Tolle in Game 1 and Sonny Gray in Game 2. After Wednesday’s season-ending loss, players voiced their frustration with the organization’s approach.
Now, we must turn the page to an offseason of uncertainty. It’s obvious that major moves need to be made if the Red Sox hope to advance past the Wild Card Series for the first time since 2021 and regain their reputation as a perennial contender. So, where does chief baseball officer Craig Breslow begin?
Here are the four biggest questions Breslow and the Red Sox face heading into the offseason:
How can the offense be fixed?
The Red Sox finished the 2026 regular season ranked 23rd in MLB in runs scored, 26th in home runs, and 20th in slugging percentage. They were dead last in runs scored in September, and that lack of production continued in the postseason when they were outscored 18-2 by the New York Yankees in the Wild Card Series.
Suffice it to say, upgrading the lineup should be Breslow’s No. 1 priority this winter, but what are the paths to doing so?
This year’s free agent class doesn’t feature many enticing options. Seattle Mariners outfielder Randy Arozarena, Chicago Cubs outfielder Seiya Suzuki, and Pittsburgh Pirates second baseman Brandon Lowe are the top three hitters set to hit free agency. If the Red Sox aren’t going to spend for one of them, they’re better off turning their attention to the trade market.
The problem is that Boston depleted its farm system at the trade deadline, sending four of its top 10 prospects to the Baltimore Orioles in exchange for All-Star catcher Adley Rutschman. With much less prospect capital to offer in deals, Breslow will have his work cut out for him in trade discussions this offseason.
Who are the odd men out?
Unless the Red Sox want yet another early playoff exit in 2027, or to miss the postseason altogether, there should be a good amount of roster turnover this winter.
Outfielder Jarren Duran and shortstop Trevor Story are clearly the top candidates to be traded. Duran is coming off a woeful season and still has two years left on his contract. Story struggled through another injury-plagued campaign, and No. 1 prospect Franklin Arias is ready to take his starting shortstop job.
Parting ways with Duran and Story would help clear logjams at their respective positions, but to bring in All-Star-caliber talent via trade, Breslow will have to get bolder. That might mean a willingness to package a key contributor like Wilyer Abreu in a blockbuster deal for an offensive upgrade. And would Boston dare give up on former top prospect Roman Anthony after his disappointing sophomore season? It doesn’t seem all that far-fetched in the immediate aftermath of his latest injury setback.
Left-handed pitchers Payton Tolle, Garrett Crochet, and Ranger Suarez are probably the only Red Sox players safe from being traded this offseason. Everyone else should at least be on the table.
What does an Adley Rutschman extension look like?
The Red Sox didn’t trade top prospects Anthony Eyanson, Kyson Witherspoon, Enddy Azocar, and Harold Rivas to the Orioles for a one-and-a-half-year rental. They acquired Adley Rutschman with the intention of signing him to an extension. The question is, what would such an extension look like given the soon-to-be 29-year-old’s inconsistency and durability issues in recent years?
Mariners catcher Cal Raleigh signed an extension with an average annual value of $17.5 million before the 2025 season. Los Angeles Dodgers backstop Will Smith’s recent extension is worth $14M per year. Rutschman is expected to look for a $20M AAV, such as a five-year deal worth roughly $100M.
Is he worth it? That’s a whole other conversation for a different day.
Who could fill the Sonny Gray void?
The Red Sox couldn’t have asked for more from Gray in 2026. The 36-year-old put up Cy Young-caliber numbers, stepping up as the rotation’s de facto ace while Garrett Crochet missed most of the year due to injury.
Unfortunately for Boston, Gray is scheduled to hit free agency this offseason. And even if he decides to hold off on retirement, his recent remarks suggest he’s probably not re-signing.
Without Gray, the Red Sox’ projected 2027 rotation is still pretty solid…
- Garrett Crochet, LHP
- Payton Tolle, LHP
- Ranger Suarez, LHP
- Jake Bennett, LHP
- Brayan Bello, Tanner Houck, Kutter Crawford, or Johan Oviedo (all RHP)
… but it would look far better with a legitimate Gray replacement.
Free-agent options include righties Michael King, Joe Ryan, Freddy Peralta, Casey Mize, and Kevin Gausman. Or, the Red Sox could trade for an arm, just as they did when they acquired Gray from the St. Louis Cardinals last offseason.
