Coming off three straight disappointing seasons, the Red Sox entered 2025 with renewed hope.

The club finally spent real money in the offseason, bringing in Garrett Crochet and Alex Bregman along with several other notable contributors, and heading into Opening Day the Red Sox were trendy picks to not only win the AL East, but potentially reach the World Series.

Now the whole thing is coming apart.

Between injuries and underperformance, the Red Sox have fallen far short of expectations. Entering the weekend the club is 28-31 and has gone 11-16 in the month of May. Now the team faces a make-or-break June where the club will not only play a stretch of 15 consecutive games from June 6-22 against teams that are currently at or above .500, but they’ll have to try to stay afloat without Bregman, the team’s best all-around player.

Perhaps the team will dig deep and find a way to stay alive — Friday was certainly an encouraging first step — but there is real danger the Red Sox could fall out of contention entirely these next few weeks.

If that happens, we could be looking at a pretty significant sell-off.

While this year’s Red Sox were built to win, they were also built with a lot of short-term pieces. If chief baseball officer Craig Breslow decided to sell he’d have no shortage of players to flip in hopes of solidifying the roster in 2026 and beyond.

What might that look like? Here’s what could happen if the Red Sox can’t turn it around.

Trade free agent starters

The first and most obvious place Breslow could start would be the starting rotation. As it stands Boston has two starting pitchers who are pending free agents in Walker Buehler and Lucas Giolito, and neither one is a sure bet to return this offseason even if they aren’t dealt.

How they pitch over the next two months will determine their ultimate trade value, but so far both have shown encouraging flashes and would likely be highly coveted on the trade market by contenders looking to raise their rotation’s ceiling. Buehler in particular could be a valuable chip given his playoff pedigree, and it’s reasonable to imagine he could fetch a pretty significant prospect return.

Plus, from the Red Sox’s perspective, the pair are borderline expendable at this point.

Even if you subtract Buehler and Giolito from the equation the Red Sox will still go into next offseason with seven starters under team control: Crochet, Brayan Bello, Tanner Houck, Richard Fitts and Hunter Dobbins plus Kutter Crawford and Patrick Sandoval, each of whom should be back on the mound by the second half. That’s a pretty solid starting point, especially if Houck can figure things out, and if the club were to add one more big arm in free agency or via trade then the Red Sox could conceivably start 2026 with one of the better rotations in baseball.

One other bonus? Buehler and Giolito are making approximately $40 million combined, so dealing them would get the club close to dipping back under the luxury tax threshold. Obviously the Red Sox shouldn’t be pinching pennies, but there’s no sense in dealing with the draft pick penalties and other baseball consequences that come with being over the luxury tax in a year where you’re likely to miss the playoffs.

Blow up bullpen

Similar to the starting rotation, Boston’s main bullpen acquisitions this offseason came on one-year deals and could be valuable trade chips for a club looking to shore things up in the late-game.

Outside of his blown save in Milwaukee on Tuesday, Aroldis Chapman has been everything the Red Sox could have hoped for. The 37-year-old is still among the hardest throwers in baseball and has been a reliable closer for a club that’s been short on bullpen stability. He’d be highly coveted.

Fellow left-hander Justin Wilson has also pitched well and could help a contender in need of another lefty, and while Liam Hendriks has struggled this season, he still has a strong track record. Perhaps there’s a team out there that believes he could still rediscover his old dominance?

Obviously without those guys the bullpen could look pretty ugly down the stretch, but at least the Red Sox could get a good look at their internal candidates and decide who has a future with the team and who doesn’t. Get Zack Kelly and Luis Guerrero up permanently, give Zach Penrod another look and see who else warrants a second-half tryout.

Call up Anthony, shake up lineup

While the pitching staff has plenty of low-hanging fruit to reach for, the position player situation is a lot stickier.

The Red Sox do not have any pending free agents among their everyday regulars, with the possible exception of Bregman, who could opt out of the remaining two years, $80 million on his deal this offseason if he chose. The Red Sox also have several high-priced veterans who remain under contract for at least two more seasons but who haven’t performed up to expectation and are blocking the paths of several of Boston’s most promising young prospects.

Somehow or another, something is going to have to be done.

The first order of business will be calling up Roman Anthony, which could conceivably happen any day now and arguably should have happened a long time ago. Anthony has dominated Triple-A despite being among the youngest players at that level and has clearly shown he’s ready for a big league opportunity. There’s no guarantee he’ll hit the ground running — Kristian Campbell and fellow former top prospect Jackson Holliday are good examples of how even the brightest young stars sometimes stumble early in their MLB careers — but if the Red Sox want to put themselves in the best position to succeed long-term, Anthony needs to come up.

That’s the easy part. The tough part is how the Red Sox can realistically accommodate him.

Given the roster’s current construction — and assuming moving Rafael Devers to either first or third base isn’t an option — there are two ways the Red Sox could get Anthony into the starting lineup. One is by moving Kristian Campbell to first base, Marcelo Mayer to second, Ceddanne Rafaela to third and putting Anthony in the open outfield spot. The other involves moving Trevor Story off shortstop, enabling Mayer to shift to his natural position, Campbell to keep developing at second and Rafaela to take over at third.

Story has largely looked lost at the plate for the past month and has also seen his normally stellar defensive metrics fall off. Perhaps he could still turn things around and get back to being the impact player the Red Sox hoped he’d be all along — again, Friday was an encouraging step — but if not the club may have no choice but to designate him for assignment.

The downside to doing that is the club would be on the hook for the remaining two years, $46.7 million of his deal plus whatever money he’s still owed for this year. The club may eventually also face a similar decision with Masataka Yoshida, who has spent the entire season on the IL recovering from offseason shoulder surgery but who would prompt another roster crunch in the outfield upon his return.

So what can the Red Sox realistically do to streamline their roster? There’s an example from the club’s past that might offer a way forward.

Reprise 2012 blockbuster

In 2012 the Red Sox were in a dark place, and beyond falling into the AL East basement the club also looked like it would be hamstrung for years by the seven-year, $142 million contract it gave in 2011 to Carl Crawford, who almost immediately became a shell of the player he was in Tampa Bay. With the team well out of contention the Red Sox found an escape hatch in the form of the Los Angeles Dodgers, who agreed to take on not only Crawford’s but also Josh Beckett’s remaining contract as part of a larger blockbuster built around first baseman Adrian Gonzalez.

There were other pieces involved as well, but essentially the Red Sox used a valuable commodity to unload their dead weight. In doing so they freed up resources that helped allow Boston to construct a World Series championship-winning roster the following year.

A similar deal in 2025 would probably involve packaging Story and Yoshida along with either Jarren Duran or Wilyer Abreu, possibly with additional prospects as well. Losing Duran or Abreu would hurt, but at some point the Red Sox are going to have to move one of their existing outfielders anyway, so this kind of deal would effectively get all of the messy business over with at once.

The end result post-trade would be a starting nine that looks something like this: Carlos Narvaez C, Triston Casas 1B (or TBD if still out injured), Kristian Campbell 2B, Marcelo Mayer SS, Alex Bregman 3B (assuming he doesn’t opt out), Roman Anthony OF, Ceddanne Rafaela OF, Wilyer Abreu or Jarren Duran OF (whoever remains), Rafael Devers DH.

That’s pretty much the group everyone has been waiting for, right? It might not be pretty at first as the young players endure their early-career growing pains, but throughout this five-year rebuild the light at the end of the tunnel was always the idea of seeing guys like Mayer and Anthony step up and become the faces of the club’s next great championship contender.

Now that vision is just about a reality, and if this year’s group can’t turn things around the Red Sox would do best to turn things over to the next generation and see what the kids are capable of.