Red Sox's 3 Keys to a Dream Trade Deadline As Sellers

There's something liberating about expecting the Boston Red Sox to sell at the trade deadline. Rather than holding out hope for a miraculous turnaround this year, it's time to take the pressure off and think about improving for next year.

We're not in the unenviable position in which chief baseball officer Craig Breslow currently finds himself -- contemplating a sell-off while pondering his own job security. We can objectively think through this deadline and talk about the types of moves that would determine success.

Each of the past few seasons have delivered a true seller's market at the deadline, and there's no reason to think this year would be any different. The Red Sox have a real chance

Max out returns for Chapman and Gray, but hold Contreras

The most obvious prizes the Red Sox have to sell off are closer Aroldis Chapman, starting pitcher Sonny Gray, and first baseman Willson Contreras. Only one is guaranteed to be under contract for next season, and that's the one the Red Sox need to pass on dealing.

Contreras is the right-handed masher the Red Sox were hoping they'd find this offseason, and he's outperforming expectations. Even as a 35-year-old next year, the fit is too perfect to let him go, even if the prospect package would be substantial.

Bring back a cost-controlled righty bat

In a trade for Gray or Chapman, or if and when they trade Jarren Duran, the Red Sox should be targeting young, right-handed power bats who are either just arriving or about to arrive in the majors. The options range from established major leaguers to high-ceiling prospects.

Chicago Cubs infielder Matt Shaw was a name Red Sox fans heard a lot in the offseason and could be available again at the deadline. A dream trade for Houston Astros shortstop Jeremy Peña probably isn't going to happen, but it's at least worth the conversation.

Offload at least one terrible contract

May 4, 2026; Detroit, Michigan, USA; Boston Red Sox shortstop Trevor Story (10) hits a single in the first inning against the Detroit Tigers at Comerica Park. Mandatory Credit: Rick Osentoski-Imagn Images | Rick Osentoski-Imagn Images

The Red Sox showed an appetite for a salary dump trade in the preseason, when they shipped Jordan Hicks to the Chicago White Sox. The instinct that Hicks wouldn't be any good was correct, and now Boston has $8 million more to play with for next year's payroll than they did previously.

At this deadline, as they bring in prospects from other clubs, the idea of shipping out at least one prospect to get rid of some of next year's money they owe Masataka Yoshida ($18.6 million) or Trevor Story ($25 million) has to be awfully tempting. It would likely get them under the second luxury tax threshold for this year as well.

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