Could Red Sox hold valuable trade pieces? Here's what MLB executives think

Monday marked the one-year anniversary of the stunning trade that sent Rafael Devers from Boston to San Francisco, a move that sent shockwaves throughout Red Sox Nation.

The Sox were hovering around .500 at the time, and although they stumbled for a couple weeks following the deal, a big second half helped them finish with 89 wins and an American League Wild Card spot before falling to the rival Yankees in three games.

This year, however, has been a different story.

The Red Sox haven’t been over .500 since Opening Day, and they have owned a losing record since dropping their first series of the season to open 1-2.

Their longest winning streak this season is three games, which they have accomplished only three times in their first 69 contests. Conversely, Boston has a five-game losing streak and three different four-game slides.

Even after taking two of three from the Rangers at Fenway over the weekend, the Red Sox were 7-13 in their last 20, falling 13 1/2 games behind the Yankees in the American League East.

Entering Tuesday, Boston sat only 5.5 games out of a Wild Card spot, as the 35-36 Athletics began the week holding that final postseason position despite a sub-.500 record. But five teams stood in between the Red Sox and Athletics, creating a crowded field that has yet to sort itself out.

There were far bigger expectations for 2026 after Craig Breslow, in his third year as Boston’s chief baseball officer, had an active offseason. He traded for Sonny Gray and Willson Contreras in separate deals with the Cardinals, then signed Ranger Suarez to a five-year, $130 million contract one week after Alex Bregman spurned the Sox for the Cubs.

The week before camp was set to open, Breslow made his final notable move of the winter, acquiring Caleb Durbin from the Brewers for Kyle Harrison, who had been one of the key pieces in the Devers trade. James Tibbs III, another one of the main prospects from the Devers deal was traded to the Dodgers last summer for Dustin May; Tibbs has 19 home runs and a 1.036 OPS at Triple-A this season.

“That was actually a good deal for them,” an NL executive said. “Look at what Harrison is doing this year and Tibbs looks like a solid outfield prospect. The problem is they moved them both too soon.”

Contreras has been Boston’s best hitter in 2026, but Durbin has struggled in his first season with the Sox, part of an offense that entered Tuesday ranked last in the AL in runs scored (278), 13th in OPS (.698), tied for last in home runs (58) and last in on-base percentage (.314).

But given their precarious position as we enter the second half of June, it’s only natural to wonder whether the Red Sox could be a team that unexpectedly enters July as a seller.

“Boston should consider selling if they find themselves in a similar position come the end of July,” a National League executive said.

Should Boston decide to sell, what pieces would be appealing to contenders around the league?

• Closer Aroldis Chapman is earning $13 million this season and has a $13 million mutual option for 2027 that figures to be declined by one side or the other.

• Gray is making $31 million in 2026 and has a $30 million club option for 2027 (with a $10 million buyout), though he can opt out and become a free agent if the option is exercised.

• Contreras is signed for $18 million this season and $18.5 million in 2027, with a $17.5 million club option for 2028.

• Outfielder Jarren Duran is earning $7.7 million in 2026 and is arbitration-eligible for two more seasons.

“I think a lot of these players have a chance to be difference makers, but here would be my questions if acquiring any of them,” another NL executive said. “You have to treat Sonny and Aroldis as one-year deals, and that’s a big buyout. Would you pay Sonny $20 million for the rest of this year? Aroldis will almost certainly opt out. The Cardinals had a hard time moving Contreras last year; how many teams want that personality on their team at the Deadline? Duran would be a sell-low [option] at this point; he has struggled to hit even though he has had some power.”

There are other players that could draw interest from clubs -- outfielder Wilyer Abreu, infielder Isiah Kiner-Falefa and reliever Garrett Whitlock, for example -- and the NL executive believes the Red Sox could try attaching a higher-priced player such as Masataka Yoshida or Brayan Bello to one of them if there is an edict to clear out some payroll.

Each of Boston’s potential trade chips comes with an asterisk of one type or another, prompting one AL executive to wonder whether the Red Sox can get enough back to justify packing it in for 2026.

“Gray’s market will be limited by his salary,” the executive said. “Contreras is an acquired taste, Duran is having a down season, and Chapman will be a rental reliever. The potential returns for that group will be tempered.”

Given the AL Wild Card logjam, the Red Sox are theoretically one winning streak away from thrusting themselves back into that race. Breslow will likely wait another month before facing a buy-or-sell decision, but the lack of big-time trade chips to move and the number of young regulars on the roster could create a tricky dilemma for Boston’s front office.

“I think that they are going to have to wait to make a call,” an AL executive said. “The arms are more interesting than the position players, but not sure even if they move them that the return will move the needle the way they need it to.”