The Chicago Cubs have had Sonny Gray circled as a possible trade deadline fit, but that idea is getting harder to treat like a straight line from rumor to reality.
Gray looked like the kind of arm Boston might move if the Red Sox decided to sell. Instead, their play this month has pulled them back into the Wild Card discussion, even if the picture in the American League is still crowded. With that in mind, there’s a real chance Craig Breslow tries to keep the club in the race, especially if he’s worried about his own future after the season.
That alone makes Gray a less obvious Cubs target. ESPN’s Jeff Passan also put the odds of a deal at just 25%, and the contract situation is a big reason why.
"On top of the $10 million or so he'd be owed in salary for the final two months -- around the same as Skubal -- Gray's restructured contract after his trade from St. Louis to Boston includes a $10 million buyout on a $30 million mutual option for 2027. Considering mutual options don't get picked up, that is a pricey deadline acquisition, leaving Boston somewhat hamstrung unless it's willing to pay down a significant portion and convince Gray to accept a deal."
There’s also the no-trade clause to factor in, and that can turn any deadline pursuit into a delicate negotiation. Gray has seemed to enjoy Boston, but he wasn’t exactly glowing about his time with the Yankees.
That has raised questions about whether he’d even want to pitch for another big-market club. Add in the fact that he liked his time with the St.
Louis Cardinals, and it’s fair to wonder whether Chicago would be a destination he’d embrace.
The money side is where the Cubs could still have some leverage. They’re already expected to go into the luxury tax this season, and their 2026 payroll is currently estimated to be above $248 million.
That gives them room to take on Gray’s remaining salary this year without crossing the second threshold at $264 million. They also have more than $100 million coming off the books after the season, which means the $10 million buyout wouldn’t be a major issue.
That opens the door to a possible structure where Chicago absorbs the money in exchange for lowering the prospect cost. But Boston’s goal in dealing Gray, if it gets to that point, would be to add to the farm system rather than simply clear salary.
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