After a few years of mediocrity, the Boston Red Sox have built an organization loaded with young talent. Chief of Baseball Operations and acting General Manager, Craig Breslow, has done a magnificent job giving the team the chance to be perennial World Series contenders.
However, the team’s deep prospect pool now puts them in an awkward situation of overcrowding, and benching their young talent isn’t in the cards.
As a result, Breslow faces some tough decisions regarding who he hangs on to, and who’s packing their bags.
What’s The Problem
It’s almost a stretch to call it a problem, but the Sox simply just have too much quality for one lineup.
For the 2026 offseason, Rob Refsnyder is the Red Sox’ only unrestricted free agent. While he’s done well in his four years there, the Sox will likely pivot to rookie Jhostynxon Garcia as his replacement.  
The only other potential free agent is Alex Bregman, who has been the best hitter for the team in 2025. Jeff Passan reported in an article for ESPN that it is likely he opts out of his player option to pursue a new contract in free agency, meaning the Sox will have competition for him.  Bregman’s agent is Scott Boras, who’s become notorious for helping his clients find the most lucrative contract and disregarding loyalty almost entirely. 
Even in a scenario where Bregman leaves, Boston would have their infield filled out, and six MLB-level outfielders. No matter what, there’s some work to be done to find space for the future.
What They Need
If Boston has one issue, it’s their starting rotation.
Garrett Crochet has led the charge as the team’s ace and a Cy Young candidate. Brayan Bello’s been a solid middle of the rotation starter. And the Sox have two promising prospects in Connelly Early and Payton Tolle, the latter of which should provide a decent depth arm next season. 
Lucas Giolito has arguably been the Sox’ second best starting pitcher this season, posting a 3.31 ERA and a 1.25 WHIP as of Tuesday. And while keeping him would be ideal, with the way his contract is structured, Giolito can opt out of his deal in search of a longer-term deal in free agency.
Giolito’s play this season should earn him a multi-year deal this off-season, so it’s reasonable to expect him to opt out in search of a longer deal than he’s currently on. 
What They Should Do
Ideally, the Sox could be rid of one or both of the Masataka Yoshida and Trevor Story contracts. But those deals are lengthy and expensive, both with two years left on their deals, at $18.6 million and $25 million annually respectively, making it unlikely another team would want to pick up either of the 32-year-olds. So, the Sox will either have to keep them, or cut them, leaving them to pay most of the contract for a player no longer on the team. 
If neither Yoshida nor Story is cut, two players the Sox would likely consider moving are Jarren Duran and Wilyer Abreu. 
Hearing those names in trade talks will be a shot through the heart of Boston fans, as both players have become fan favorites in recent years. To get good players, though, you need to give up good players, and if Boston wants to find their next star pitcher via trade, one of those two names would likely be the easiest for the team to part with. 
The Philadelphia Phillies could be a fit for a trade. With rookie Andrew Painter slated to enter the Phillies’ rotation next season, and outfielders Max Kepler and Harrison Bader as well as DH Kyle Schwarber all hitting free agency, the Phillies could be on the hunt for another outfielder with a quality bat. Depending on their aggressiveness in free agency regarding starting pitching, Philly could be open to moving Jesús Luzardo or Taijuan Walker, for the right price. 
Another team that could be interested is the Seattle Mariners. Right fielder Victor Robles hasn’t been amazing this year, posting only a .624 OPS, and he has a poor injury history. Due to impending free agents such as Josh Naylor, the Mariners could be on the hunt to shed the remaining 3 years and $72.45m on Luis Castillo’s deal.
If Seattle isn’t looking to move Castillo, the Sox could still make a push for one of George Kirby or Bryce Miller, two 27-year-olds having down years following great 2024 campaigns. Either one could be a good candidate for the Sox to buy low on in hopes of a bounce-back season. 
That being said, the Sox don’t necessarily need to make a move if Bregman leaves. There are bound to be injuries, and some of the younger players can be sent down to Triple-A Worcester if necessary, so having an excess could provide the Sox with a cushion in the event somebody goes down. 
In the event the Sox aren’t active in the trade market, they could pivot toward free agency. San Diego Padres’ starter Michael King could be a good option, and his 2.87 ERA and 1.07 WHIP make it likely that he’ll decline his end of the mutual option in search of a long, lucrative deal. 
In the event Bregman re-signs, the team may be more likely to make a splash in the trade market. Namely, Joe Ryan would likely be on their radar, along with those mentioned earlier, though Minnesota would be less likely to ask for Abreu or Duran as opposed to younger prospects.
There are quite a few other names the Sox may gun for, but only time will tell what direction they go in. 
For now, though, the team’s focus is on October baseball.