Boston Red Sox

Sell or Regret It: The Red Sox Have to Trade Chapman and Gray

The Red Sox are 36-46. Last in the AL East. Twelve and a half games out of first. You know this. You’ve been trying not to think about it. But the July 30th trade deadline is coming whether you like it or not, and Boston is sitting on two of the most valuable arms in baseball.

Trade them. Both of them. Now.

Aroldis Chapman at 38 years old is somehow the most dominant closer available on the entire market. A 2.19 ERA. Twenty-eight consecutive saves. A 97.5 mph average fastball that sits in the 92nd percentile. Per NBC Sports Boston’s breakdown of Boston’s most likely trade candidates, the Dodgers, Phillies, Mariners, and Rangers are all circling. The trade floor per scouts — according to MassLive — is two prospects including a top-100 type. That’s the floor.

The contract wrinkle is the actual negotiating weapon here: Chapman’s $13M option for 2027 vests at 40 IP. He’s at 24.2 innings right now. Any team that acquires him inherits that option the moment he crosses 40 IP. Which means Boston can market this as a near-vested option on the best setup-to-closer arm in baseball, or it can structure the deal specifically around that threshold. Smart teams with contender windows will pay a premium for a 97-mph closer who comes with an affordable (by modern standards) guaranteed year. The Red Sox front office better know this and use it. If they don’t, that’s on Craig Breslow.

Speaking of Breslow — he’s been publicly non-committal about the deadline. That’s a bizarre posture when you’re 12.5 out with 80 games to play. What’s unclear? The standings? The math? It reads like front-office cover to avoid making a hard call, and Red Sox fans deserve a straighter answer than that.

Then there’s Sonny Gray. Nine wins, 2.69 ERA, 1.11 WHIP across 15 starts. Tied for second in the majors in wins. He’s got a full no-trade clause, and he knows it — but he also said he’s “open to a conversation,” with Atlanta reportedly the most likely destination given his Nashville ties. This one’s trickier. You can’t force him anywhere. But if he’s willing to waive for the right situation, Boston should be facilitating that conversation right now, not waiting until July 28th when everyone’s desperate and leverage is gone.

The 2016 Chapman trade is the model. Yankees flipped him to the Cubs mid-season and got back Gleyber Torres plus three others. A rental closer. A rental! That haul built a playoff roster for years. Chapman is currently on a better run than he was then.

FOX Sports’ 2026 trade deadline tracker has Boston already expected to move Chapman. The market is real. The demand is real. The only question is whether Boston extracts full value or gets cute and holds into late July hoping the standings magically reverse.

They won’t reverse. This team is not a buyer.

Jon Morosi already has Chapman ranked second in his top five deadline players. The market has spoken:

The prospects Boston gets back from trading Chapman and Gray become the bridge to whenever Roman Anthony is healthy and Roman Anthony is actually Roman Anthony again. That’s the real play. You don’t let two controllable-ish arms walk for a compensatory pick and a prayer.

Trade them. You’ll be angry about it for two weeks. Then you’ll be watching a top-100 guy rake in Salem and you’ll feel slightly better.

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