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Red Sox’s MLB Trade Deadline Plans Take Unexpected Twist

Chad Tracy, Boston Red Sox
May 16, 2026; Atlanta, Georgia, USA; Boston Red Sox interim manager Chad Tracy (17) in the dugout before a game against the Atlanta Braves at Truist Park. Mandatory Credit: Brett Davis-Imagn Images

The Boston Red Sox have widely been viewed as clear sellers with the MLB trade deadline approaching, but a recent hot stretch may have completely changed things for the squad.

After sweeping the New York Yankees in a four-game series at Fenway Park, the Red Sox defeated the Washington Nationals on Monday night for their fifth straight win.

Boston is still just 37-46 on the season, but it sits just three games in the loss column out of the American League’s final Wild Card spot with plenty of time left.

Sonny Gray, Willson Contreras, Jarren Duran and Aroldis Chapman have all been floated as prime trade candidates between now and Aug. 3, but the Red Sox may have other plans now.

Boston was expected to contend for the AL East division title this season, but an anemic offense and some hard luck have resulted in the Sox spending most of the campaign in the basement.

However, the Red Sox own a plus-8 run differential, so there is reason to believe that the team can potentially make a run over these next few months.

This doesn’t necessarily mean that Boston will go into all-out buying mode at the trade deadline, but the front office may decide to put a hold on selling off its top pieces for now.

Of course, a whole lot can happen over the next four-plus weeks. The Red Sox could go back into another tailspin, which would almost certainly result in top executive Craig Breslow deciding to sell.

But for now, Boston has somehow wriggled its way back into playoff contention, and given how high expectations were going into the season, it would surely aggravate the fanbase to sell now.

The Red Sox won 89 games last year and made their first playoff appearance since 2021, only to lose to the Yankees in the Wild Card Series.

Boston lost Alex Bregman to free agency over the winter, but bolstered its pitching staff and added Contreras to build what appeared to be a solid roster.

We’ll see if the Red Sox can turn things around in Beantown.

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