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BOSTON, MASSACHUSETTS - AUGUST 16: The principal owner of the Boston Red Sox, John Henry, is seen during a pre-game ceremony prior to a game against the Miami Marlins at Fenway Park on August 16, 2025 in Boston, Massachusetts. (Photo by Jaiden Tripi/Getty Images)

The Boston Red Sox continue to slide out of postseason contention. They are now 14 games below the .500 mark and have the second-worst record in the American League at 29-43. They have also lost four consecutive games.

At this point, it’s clear that the Red Sox are not going to be adding anything at the trade deadline other than prospects. This means that their most likely path forward this year is selling. They have a few players on expiring contracts that could be moved.

Left-hander Aroldis Chapman is one of them. Mark Feinsand of MLB.com listed Chapman as a top potential trade candidate and had the Chicago White Sox as a possible fit for the 38-year-old closer.

“The ageless left-hander continues to dominate at age 38, posting a 0.44 ERA in his first 21 appearances while converting all 14 save opportunities this season,” Feinsand wrote. “Chapman is no stranger to summer trades; he’s been dealt twice during the season (2016 to the Cubs, 2023 to the Rangers), winning the World Series in both years. Chapman is earning $13.3 million this season and has a $13 million mutual option for 2027 that will likely be declined, sending him back to the free-agent market.”

Red Sox, White Sox Have Made Deals Before

Chapman’s ERA went up to 0.83 on Thursday night as the Red Sox lost another tough game. Things are simply not going well for the Red Sox.

However, the White Sox are a familiar trade partner. Boston acquired Chris Sale from the White Sox after the 2016 season. After the 2024 season, the Red Sox conducted business with the South Siders again, acquiring Garrett Crochet.

The difference this time is that the Red Sox would the ones selling while the White Sox would be looking to add. The White Sox received a lot of solid young players for Crochet back in 2024. If they were to use some of that prospect capital to bring in Chapman, they could potentially boost their roster for a run in the second half of the season.

The Red Sox would be setting themselves up well for the future as well, and they could put themselves in position to potentially bounce back into contention sooner rather than later. Chapman may not get them a lot in terms of quantity, but they could bring back a solid prospect or two to get the deal done.

At this point, the Red Sox are out of contention, and it’s going to take a complete turnaround for them to reach the playoffs, even in the weak American League.

Chapman Will Likely Enter Free Agency

Chapman has a mutual option for 2027, but those are rarely exercised, so he will likely enter free agency once again this offseason, which is why it makes sense for the Red Sox to trade him. The White Sox can give them what they need in exchange, and they can capitalize on his value while they still have the opportunity.

He is having one of the best seasons of his career, so it will be tough to keep him after 2026 anyway.