Sweeping the New York Yankees to help wrap up June won’t even be enough to salvage the 2026 Boston Red Sox. Moral victories in the middle of a lost season are appreciated. The bigger win will come at the Aug. 3 trade deadline. The Red Sox didn’t plan to become trade deadline sellers much like the St. Louis Cardinals didn’t expect to actually compete this year. The irony, with the two teams making two major trades in the offseason, shouldn’t be lost on anyone.
With a month to go, the Red Sox will need to evaluate their roster carefully and decide if this is a full tear-down or a more minor sell-off. Whichever Craig Breslow decides, these five Red Sox players need to be up for grabs. Some are more important to deal than others.
5. Sonny Gray – Must sell at a high

Sonny Gray was the piece acquired from the Cardinals this offseason meant to push Boston into World Series contention. He’s under control again next season on a mutual option of $30 million with a $25 million hit to the luxury tax. At a spectacular 9-1 with a 2.69 ERA this season, he should be someone any team contending now and with plans to do so next year should covet.
A bit unpredictable throughout his career, with a different version showing up at every stop he has in his career, the Boston version has been exactly what they needed. Gray is probably the most complicated trade candidate on this list because of how good he has been. His last outing pushed him over 2,000 career innings. It might be better to cash this ticket in now rather than let him fall apart in your uniform.
4. Danny Coulombe – Must sell for anything you can

Not high-profile but worth noting, Danny Coulombe has underachieved with a 4.58 ERA and 4.58 FIP this year to tell us it’s not good or bad luck. He is what he is and that’s a very average pitcher. Lefties are hitting .286 against him but with no extra-base hits. His biggest issue has been walking 11 batters versus only 10 strikeouts.
He’s someone the Red Sox should trade ASAP because there is a clear ceiling as to how much anyone would give up to get him.
3. Aroldis Chapman – Sell him before you regret it, but be willing to regret it

It’s probably better to get out from Aroldis Chapman while you can. The unpredictable nature of a relief pitcher, especially a closer nearing 40, should have the Red Sox firing off phone calls and texts to everyone they can.
Chapman has a 2.19 ERA this season on a contract that pays him $13.3 million this year and next. We saw how the New York Yankees went after controllable relievers last season. A deal between those two clubs feels a little too unlikely.
What about one of his other former clubs, the Chicago Cubs? No one on their roster has saved more than three games all year.
4. Willson Contreras – Sell him only if the price is right

Willson Contreras is former Cardinals player who got to keep his red socks when he was traded from St. Louis to Boston. He has done well, hammering 18 home runs with a .906 OPS. One has to wonder why he didn’t move to first base earlier in his career.
With just over $17 million owed to him for next season, he’s affordable for the production he puts on the field. Contreras could either end up as one of the best controllable players traded this summer or a guy the Red Sox go to battle with next year. A reason to trade him would be that teams might in fact view him as a missing piece to their lineup.
It might be nice to see him go to a team that typically doesn’t spend high on free agents such as the Cleveland Guardians or Miami Marlins. Both of them could use some offensive firepower.
5. Jarren Duran – Wait until the offseason

Jarren Duran trade rumors won’t go away until he wears another team’s uniform. On the interstate with a .196 batting average, the Red Sox missed their chance to maximize a return. It still wouldn’t hurt to discuss him in trades as the team has to move on from him eventually. His shrinking trade value due to a poor season is something they should be careful about.
In the offseason, with two years of arbitration eligibility left, non-contenders could come calling with more impressive offers. Some of them could include MLB-ready players to immediately help the Red Sox turn things in the right direction.
