The Boston Red Sox are doing their darndest in an effort to avoid a sell-off at the trade deadline, winning six straight and 11 of their last 13. That has them sitting at 43-48 just days away from the All-Star Break, which is enough to put them on the periphery of the Wild Card race in a very weak American League.
Then again, sweeping the reeling Yankees, lowly Angels, and upstart White Sox isn't exactly proof that all that ails this team is fixed. Odds are that they'll still be willing to at least listen to offers for their best trade chips.
Maybe they could try to perform a tightrope act as a buyer and seller, though you'd be hard-pressed to find a Sox fan that would trust Craig Breslow to do that. Instead, he'll need to pick one lane or another, and do his best to avoid trade proposals like these:
The Chicago Cubs have a log-jam in the infield and desperately need pitching help. The Red Sox have the opposite problem and are likely sellers this deadline
— Thomas Nestico (@TJStats) July 8, 2026
Here is my trade proposal which sends star closer Aroldis Chapman and Sonny Gray to Chicago https://t.co/DChx6zESZb pic.twitter.com/eY2PLupP0y
With all due respect to Thomas Nestico, the creator of the excellent TJStats page, this is such a laughably bad and lopsided proposal that it's hard to offer any notes. Gray and Chapman are two of the most premium pitchers available this summer; accepting an underpay of this magnitude would all but ensure Breslow's ticket out of town.
If Red Sox sell, they can't afford to get Sonny Gray and Aroldis Chapman trades wrong
The Cubs are frequently mentioned as a suitor for the Red Sox's best pieces, both because of their desperate need for pitching and Breslow's connection to the top executives running the show in his old home. However, they could easily do a lot better than an offer built around Pedro Ramirez and Brooks Caple; for both Gray and Chapman, you'd have to be talking about at least two top-100 prospects.
That may seem like a steep price to pay for two older rental pitchers, but they are two of the best available arms on the market. Gray does have more competition thanks to the presence of Tarik Skubal and Joe Ryan, but he's been sterling all year long (2.61 ERA) and can adjust his game based on the quality of the defense behind him.
Meanwhile, Chapman remains impossibly effective for a 38-year-old closer, even as he's struggled recently while pitching through a hamstring issue. High-leverage relievers are always a hot commodity this time of year, and no one out there can match the southpaw's blend of win-now talent and postseason experience.
If the Red Sox stumble again prior to the trade deadline, both pitchers should be shipped out; expiring contracts hold little value for a losing team, especially when the player in question has already received a qualifying offer (in Gray's case). But just because they're goners doesn't mean the front office should accept anything less than peak value for them. Gray and Chapman could bring in the kind of package of players that enables this roster to compete again as soon as 2027.
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