Red Sox's 3 Must-Shop Trade Chips Entering Deadline Season

Who should be on the move?

May 20, 2026; Kansas City, Missouri, USA; Boston Red Sox catcher Carlos Narvaez (75) and Boston Red Sox relief pitcher Aroldis Chapman (44) celebrate after defeating the Kansas City Royals at Kauffman Stadium. Mandatory Credit: Jay Biggerstaff-Imagn Images | Jay Biggerstaff-Imagn Images

The Boston Red Sox are almost guaranteed to be in an awkward position at this year's trade deadline.

Mired in a 23-32 start to the season, the Red Sox face long odds to climb into surefire playoff position within the next two months. That means they'll have to consider trading away veterans by the Aug. 3 trade deadline, and yet, the weak American League means they probably won't be totally out of contention, which would make the selling decision easy.

So for now, the Red Sox simply have to shop their top trade chips to gauge where the market stands. These are the top three players who would make sense to trade, and who could net them the most appealing returns.

1. Aroldis Chapman

May 16, 2026; Atlanta, Georgia, USA; Boston Red Sox pitcher Aroldis Chapman (44) enters a game against the Atlanta Braves in the ninth inning at Truist Park. Mandatory Credit: Brett Davis-Imagn Images | Brett Davis-Imagn Images

It's amazing to think that Chapman spent 2022 through 2024 as primarily a non-closer. At this point, he's back to a top-three guy in the sport, and if the Red Sox moved him while he's this dominant (0.51 ERA in 17 2/3 innings thus far), they'd be almost guaranteed to get multiple high-ranking prospects back.

Note that Chapman also has a $13 million player option for next year available if he hits 40 innings pitched, so he's not a true rental. That could be an argument to keep him around and hope he opts back in for 2027, of course, but also... will we even have a baseball season next year?

2. Sonny Gray

May 24, 2026; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Sonny Gray (54) pitches during the first inning against the Minnesota Twins at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images | Bob DeChiara-Imagn Images

The only true rental with any trade value on this Red Sox team, Gray is sporting a 5-1 record with a 122 ERA+ through his first nine starts in Boston. He's also started striking out more batters since returning from the injured list, which should boost his trade value over time.

This is the most clear-cut decision the Red Sox have: If they're ready to punt on this season, they should move on from the 36-year-old Gray. If they think they're still a viable playoff contender, Gray should stay.

3. Jarren Duran

May 20, 2026; Kansas City, Missouri, USA; Boston Red Sox left fielder Jarren Duran (16) hits a home run during the seventh inning against the Kansas City Royals at Kauffman Stadium. Mandatory Credit: Jay Biggerstaff-Imagn Images | Jay Biggerstaff-Imagn Images

This list easily could have run in reverse order, because if Duran keeps heating up, he'll be so desirable that the Red Sox will have to think twice about shipping him off. There's something to be said for the fact that Roman Anthony and Wilyer Abreu have both spent significant time on the injured list over the last calendar year and Duran has been the picture of health.

But of course, we've been hearing Duran trade rumors for two years now, so we can at least expect the Red Sox to keep throwing his name around at the water cooler to see what teams are willing to give up.