Popular Cubs trade deadline target suddenly looks much more complicated

As the Chicago Cubs have mapped out their path to the trade deadline, Boston Red Sox starting pitcher Sonny Gray has been a popular target. If the Red Sox were going to sell, moving Gray felt inevitable. Now, the conversation isn't as simple.

While the American League East still appears to be out of the Red Sox's reach, their play this month has allowed them to climb back into the conversation for a Wild Card spot. It's a crowded picture, but given the chaos that has surrounded Boston this season, there's a chance that Craig Breslow will look for any opportunity to keep his team in that conversation. Especially if he's facing the possibility of losing his job after this season.

For that reason alone, perhaps the Cubs don't have the clearest of paths to Gray. Making things even worse, Gray's contract status is complicated. It's why ESPN's Jeff Passan only put a 25% chance on the veteran starting pitcher being moved this summer.

"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."

Cubs potential pursuit of Sonny Gray may face roadblocks

As to the no-trade clause, that can be a tricky conversation. While Gray seemingly has enjoyed his time in Boston, he didn't speak fondly of his run with the Yankees. It's led to some question if he's interested in pitching for a big-market team. Between that and Gray enjoying his time with the St. Louis Cardinals, it's certainly possible he doesn't have an interest in joining the Cubs.

As for the financial element to the conversation, there's a possibility that works in the Cubs' favor. It's still a costly addition, but the Cubs are already expecting to enter the luxury tax this season. The Cubs 2026 payroll is currently estimated to be over $248 million. If they wanted, they have space to absorb the remaining money owed to Gray this season without going over the second threshold at $264 million. The then have over $100 million coming off the books after the season, so Gray's $10 million buyout wouldn't be a burden.

Perhaps there's a scenario where the Cubs offer to take on the remaining money owed Gray as a way of lowering the prospect cost in a potential trade. Though, for the Red Sox, the purpose of trading Gray should be more about restocking their farm system, and not saving money.

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