Red Sox Trade Deadline: Four Stars to Keep (and Two Deals to Make)

Could this be the moment the Boston Red Sox's season turns around?

Boston has won five games in a row, including a four-game sweep over the New York Yankees over the weekend, and there isn't a starting rotation out there more on fire than the Red Sox's right now. Boston built this team with the idea of run prevention in mind with good pitching and good defense. Despite the fact that Garrett Crochet is on the Injured List and Brayan Bello is down in Triple-A, the Red Sox's rotation has been on a heater with 12 straight quality starts and the offense is starting to wake up, led by Willson Contreras, Ceddanne Rafaela and Caleb Durbin.

Boston kicked off a three-game series against the Washington Nationals on Monday night and came out on top, 6-3, despite the fact that Contreras was ejected from the contest in the second inning for tapping his helmet after being called out on a check swing. With the win, Boston is now 37-46 on the season and 4 1/2 games out of a playoff spot. Between now and the All-Star break in the middle of July, Boston has a schedule that should lead to wins. The Red Sox have two more games against the Nationals, three games against the Los Angeles Angels, three games against the Chicago White Sox, and three games against the New York Mets. While Boston is nine games under .500 right now, if it continues to pitch like it has over the last two weeks, that number should shrink over the next two weeks.

If Boston is able to claw itself back into the playoff race in the American League, that certainly could change the perception of the club before the August trade deadline. As of late last week, the buzz around the club certainly shifted to the idea of potentially selling with guys like Aroldis Chapman and Sonny Gray being talked about the most. The Red Sox are certainly in an intriguing spot. With that being said, let's take a look at a few of the club's potential trade candidates and whether they should be moved or not.

Keep

Sonny Gray, Starting Pitcher

Jun 23, 2026; Denver, Colorado, USA; Boston Red Sox starting pitcher Sonny Gray (54) pitches in the first inning against the Colorado Rockies at Coors Field. Mandatory Credit: Isaiah J. Downing-Imagn Images | Isaiah J. Downing-Imagn Images

The American League is weak. There are just five teams above .500. If this version of the Red Sox is here to stay — which is a big if — then they shouldn't sell off all of their big-name pieces. Gray has been a revelation for the Red Sox this season. He has a 2.69 ERA in 15 starts and a 9-1 record. If Boston can get back into the playoff race, Gray isn't going to go anywhere.

Aroldis Chapman, Closer

Jun 27, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Aroldis Chapman (44) pitches during the ninth inning against the New York Yankees at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images | Bob DeChiara-Imagn Images

Like Gray, Chapman has been talked about as a potential trade chip. If he were to become available, he would be the best overall reliever available at the deadline. But, if the Red Sox have a shot at a playoff spot, it would be surprising to see them trade their star closer away.

Willson Contreras, First Baseman

Jun 29, 2026; Boston, Massachusetts, USA; Boston Red Sox first baseman Willson Contreras (40) bats against the Washington Nationals during the second inning at Fenway Park. Mandatory Credit: Brian Fluharty-Imagn Images | Brian Fluharty-Imagn Images

Even if the Red Sox sell, Contreras should not be on the move. The All-Star slugger is having the best offensive season of his career to this point and is under contract beyond the 2026 season. Much has been said about how the Red Sox need more right-handed offensive firepower. That is true. But Contreras is a middle-of-the-order bat the club needs. Plus, he's a leader in the clubhouse.

Jarren Duran, Outfielder

Jun 18, 2026; Boston, Massachusetts, USA; Boston Red Sox left fielder Jarren Duran (16) looks on after striking out against the Toronto Blue Jays during the second inning at Fenway Park. Mandatory Credit: Eric Canha-Imagn Images | Eric Canha-Imagn Images

The Red Sox outfielder has been in trade rumors over the last few years, but it wouldn't make sense to flip him right now. Roman Anthony is on the Injured List and it's unclear when he will return. Plus, if the Red Sox were to trade Duran, they wouldn't get a great return because he has struggled offensively this season.

Trade

Patrick Sandoval, Starting Pitcher

Boston Red Sox starter Patrick Sandoval — Left-handed pitcher Patrick Sandoval makes his first rehab start with Triple-A Worcester on April 8, 2026, after undergoing surgery on his left elbow in 2024. | Ashley Green/WooSox Photo / USA TODAY NETWORK via Imagn Images

The Red Sox are about to get Patrick Sandoval back as an option for the big league club. With the rotation firing on all cylinders, the club shouldn't mess with it too much. Sandoval could be a valuable trade chip himself. If the Red Sox dealt him away, they could add pieces elsewhere without hurting the big league club.

Zack Kelly, Reliever

May 1, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Zack Kelly #76 pitches against the Houston Astros during the sixth inning at Fenway Park. Mandatory Credit: Brian Fluharty-Imagn Images | Brian Fluharty-Imagn Images

Kelly isn't on the big league roster right now, but he could be an intriguing trade chip himself. He has a 3.31 ERA in 10 outings in Triple-A. He has also made 17 appearances in the majors and has a 3.31 ERA in the big league as well. He recently opened up in an interview with Chris Cotillo of MassLive.com and acknowledged that he likes the Red Sox organization, but that he "wouldn’t necessarily be opposed" to some sort of opportunity to get back to the majors, even if it wasn't in Boston. If the Red Sox want to toe the line between buying and selling, Kelly is someone who could bring some value back.

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