Red Sox fans will hate MLB insider’s early trade deadline plan that moves on from fan favorite

Some of the Boston Red Sox's most painful roster moves in recent years have come via the trade market. Watching a slate of former Red Sox hurlers headlined by Chris Sale spin gems for other teams is tough to swallow, and then there’s the Mookie Betts debacle that signaled a downhill trajectory in team priority aimed firmly at the profit line.

But Willson Contreras is firmly outside this hall of dubious fame. Contreras came to Boston in December in a trade with the Cardinals that sent three players, including Hunter Dobbins, to St. Louis. Contreras is on pace for his first 30 home run season while sporting the fourth-best fWAR and OAA among MLB first basemen with the sixth highest OPS to complement his defense.

Sadly, with the way things are going in Boston, this means Contreras will be a hot commodity when the trade deadline draws a little closer. Russell Dorsey at Yahoo! Sports has highlighted Contreras as a player high on the trade radar. As it stands, the Sox are 2.5 games down from the Orioles to bring up the basement of the American League East, but still shockingly just 4.5 games off the final Wild Card spot in a brutally deflated AL.

Somehow more shocking still is a report from that Craig Breslow is not in jeopardy of losing his job in the coming weeks or months. Insiders claim discussions of that potential outcome haven’t even taken place. That’s hard to believe, especially given the surprise housecleaning orchestrated by Breslow to oust Alex Cora and his coaching staff.

That drastic move was meant to turn things around, but instead we’ve seen more of the same end result to baseball games with different faces at the press table (alongside a commitment to continue paying Cora the second highest managerial salary in baseball through the end of next season to sit at home).

Trade deadline strategy will clarify the Red Sox's future, but fans almost certainly won’t like the outcome

Over the next few weeks some key cogs will return to the lineup. Brayan Bello might overcome whatever is plaguing his disastrous campaign on the mound this year after his bombshell demotion to Triple-A. Garrett Crochet and Roman Anthony are still shelved with no clear timeline for their returns. There’s also Triston Casas to consider. His timeline is equally unclear, but if Casas can come back healthy he may add some new power into a lineup desperate for the threat of the long ball.

Similarly, if the AL continues to play shoddy baseball the Sox’s management may feel compelled to add at the deadline rather than sell. For his part, Breslow has been vocal about his intention to do just that. If the Sox are indeed sellers though, standout performers like Contreras will be highly sought after trade pieces, leaving the lineup even weaker. The final months of the season will be immensely painful to watch if the Sox sell and aim to reset going into the winter.

But the threat of an extended lockout makes a rebuilt a little more complicated. Paired up with a terrible AL side, the team may feel like risking it and making a push to drive into the postseason. A lights out rotation and some newly found power from a trade acquisition could potentially make the team a scrappy underdog contender. But to do that the leadership group will want to commit to keeping Breslow around. Letting a lame duck call the shots at a trade deadline buying opportunity is a great way to gum up the works for whoever is tasked with the subsequent roster overhaul.

Unfortunately there’s a third path, and perhaps one that’s the most likely outcome given Breslow’s history at the helm. The Sox may refuse once again to deal from an overcrowded outfield mix, fail to move pieces like Sonny Gray, a surging talent but pitching in the twilight of his MLB career at 36, Aroldis Chapman, an even more fearsome — and older — arm that could truly line up a contender as a team to beat in October, and of course, Contreras. If the Sox do nothing, or add at the fringes while overpaying for rentals, don’t expect to see much change in ’26 while also allowing talent to walk, regress, or even retire in the offseason when the threat of a protracted 2027 season grows larger.

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