Yankees could watch Red Sox teardown begin early after costly Cubs injury

New York Yankees fans have reveled in the Boston Red Sox's 2026 season, which has been an unmitigated disaster so far. With one of the worst records in Major League Baseball, the Red Sox are widely expected to be sellers at the trade deadline. Boston's top candidates to be traded -- according to MLB insider Mark Feinsand -- include Sonny Gray, Aroldis Chapman, Willson Contreras, Jarren Duran, and Brayan Bello.

The deadline is still more than five weeks away, but the Red Sox chief baseball officer Craig Breslow might already be fielding urgent phone calls from buyers, most notably the Chicago Cubs. Could Boston's sale commence earlier than assumed? Like ... this week?

Cubs have every reason to trade for Red Sox starter Sonny Gray

Chicago's starting pitchers are dropping like flies these days. Ben Brown and Edward Cabrera have just hit the Injured List, joining Jameson Taillon. Moreover, Matthew Boyd is just now returning from knee surgery and will surely need to be eased along.

The Cubs are right in the thick of the National League Wild Card picture and can't afford to lose pace amid this decimation to their rotation. It's definitely time for Cubs president of baseball operations Jed Hoyer to call up Breslow and make a deal for Sonny Gray, a guy who is quite familiar with the NL Central.

Sonny Gray is going to be the first domino to fall in the Red Sox's blowup, isn't he?

There are other reasons beyond Chicago's pressing needs for the Red Sox to trade Gray right now. Gray is 9-1 this season and just pulled off his best outing of the year (an 11-strikeout gem). In other words, Gray's stock is quite high right now, and it would behoove Boston to put him in a deal before that stock lowers at all.

Gray is 36 years old. At any moment in a subsequent start, he could suffer an injury. He's already missed some time in 2026 due to a hamstring strain. Every day that Breslow waits to move Gray, something could happen to lower the right-hander's value.

Oh, and there's also the fact that Gray 100% wants to be traded. We know this because he's basically implied it during recent interviews - if you'd like to talk about his no-trade clause, come on over!

Craig Breslow will probably find a way to fumble a glorious offer for Sonny Gray

Yankees fans shouldn't necessarily expect Gray to be gone by his Sunday night start against the Bombers at Fenway Park. Knowing Breslow's recent track record, he'll overthink the Gray situation and find a way to botch negotiations with Hoyer, even if they're happening at this very moment and Hoyer is offering a haul.

Gray is scheduled to close the series against the Yankees, the team he's lied about both hating and loving in the past. It sure would be fitting if that ended up being Gray's last start in a Red Sox uniform.

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