The Red Sox may be sitting on one of the strangest trade-deadline decisions in the league, and it centers on Aroldis Chapman.
Usually, the logic is simple enough: if a team is in the playoff hunt, it keeps its stars; if it’s out of the race, it sells. Boston, though, has a setup that doesn’t fit neatly into either box. The club could, in theory, move Chapman and still keep pushing to stay in the American League Wild Card race.
That possibility exists because Chapman’s contract has a built-in wrinkle. If he reaches 40 innings pitched this season - something that looks close to a sure thing if he stays healthy - his $13 million salary for next year becomes locked in.
It’s not a club option or a player option. It’s a vesting option, which means the second year is triggered automatically once he hits that workload.
At the same time, Chapman has remained a valuable late-inning arm even with a few more rough edges than he showed in his incredible 2025 season. His walk rate has climbed from 6.7% to 9.9%, and he stopped running a sub-one ERA in late June. Even so, he still owns a 2.20 ERA and can still bring 100 mph heat from the left side with serious extension.
Boston’s recent surge has changed the mood around the deadline, too. The Red Sox’s nine-game winning streak has largely quieted the talk of a full-scale sell-off. They were still two games under .500 as of Thursday, but they were also just half a game behind the Seattle Mariners and Minnesota Twins for the final AL Wild Card spot.
That’s why Chapman has become such a fascinating name. ESPN’s Jeff Passan and Kiley McDaniel have both consistently projected him as more likely to be traded than most of his teammates, and the reasoning is obvious: his value may never be higher. He could wind up as the top reliever moved before the deadline.
There’s even a path where Boston gets creative. The Red Sox could deal Chapman for a prospect package, then use prospects from elsewhere to bring in help for a playoff push. Garrett Whitlock, meanwhile, looks like a capable in-house option to handle the ninth inning.
Still, the most likely outcome is the simplest one. If Boston keeps the rest of its core intact, Chapman probably stays, too. But this is one situation worth watching closely.
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