Four players Red Sox should move and one they should keep at trade deadline

The MLB trade deadline is now less than two months away. With the season going sideways in a major way for the Boston Red Sox, it's time to make some difficult decisions. That means selling at the deadline and hitting the reset button.

What's interesting is that the Red Sox have some very valuable pieces. So, once Boston gets around to selling off those pieces, it'll have options. That includes these four players who should be on the move, as well as one popular trade candidate whom it should hold onto.

Trade SP Aroldis Chapman

When Aroldis Chapman landed in Boston ahead of the 2025 season, he was on a career downturn. Then, he had a renaissance, putting together arguably the best season of his career. His 1.17 ERA was a career low, and his 32 saves were the most he had since 2019. 

2026 has seen Chapman's usage go down, in part because the Red Sox don't have many leads to protect late in games. Still, he's been elite when pitching, to the tune of a 0.44 ERA. There's no doubt a contender would jump on adding him, and the Red Sox can get good value.

Trade OF Jarren Duran

At his best, Jarren Duran finished eighth in MVP voting. That was in 2024, though, and he's struggled to live up to that success since then. In particular, he's hitting just .214 with a .668 OPS in 2026.

The Red Sox have shopped Duran in the past with too high an asking price. This would, admittedly, be selling low on him, too. However, with too many starter-quality outfielders on the roster to play every day, Boston needs roster spots there and help elsewhere. 

Trade SP Sonny Gray

It's the first season for Sonny Gray in Boston after getting traded from the St. Louis Cardinals this offseason. So far, it's been a good deal for the Red Sox, with the Cardinals eating half of his contract's cost. Gray has a 3.03 ERA and 1.203 WHIP, both improvements from a season ago.

Because St. Louis is eating half his contract, Gray won't actually cost much out of the pocket for whoever would trade for him. On top of that, veteran starters tend to be valuable at the trade deadline. Given that he seems outside of Boston's long-term plans, it makes a good deal of sense to get something in return for him.

Trade IF Isiah Kiner-Falefa

An under-the-radar signing in the offseason for the Red Sox was the addition of utility man Isiah Kiner-Falefa to a one-year deal. In somewhat limited chances, he's played well, hitting .272 while only making one error in the field.

At the same time, the Red Sox will likely want to give younger players opportunities to learn on the fly. So, finding a new home for a veteran with positional versatility is worthwhile, especially if they can get the right deal in return.

Keep 1B Willson Contreras

Many experts expect Willson Contreras to get traded. With a .299 batting average and 16 home runs, he's on pace to have the best season of his career offensively. There's no doubt the Red Sox could get plenty back for him, and Jeff Passan of ESPN even recently ranked him as the ninth-best trade candidate. 

Except, there's no reason for Boston to trade him. Contreras has proven his swing is made for Fenway Park, and the Red Sox are desperate for power. They can't lose his bat. In particular, because he's also under contract in 2027, there's no reason to expect anything of Triston Casas in the future.