The Red Sox may be chasing October right now, but the bigger headache could come after the 2026 season ends. Sonny Gray’s contract situation is shaping up to be one of the most delicate decisions Boston faces, and it comes with a $30 million wrinkle that could send him elsewhere.
Tim Kelly of Bleacher Report pointed to the issue this fall and winter, noting that Gray’s mutual option puts the Red Sox in a bind. Boston would almost certainly pick up its side of the deal, but Gray has every reason to consider turning it down.
"Considering he'll pitch next season at 37, he's probably not going to get more than $30 million for 2027 as a free agent," Kelly writes. "However, if he declines the option, the Red Sox will owe him a $10 million buyout."
That buyout is where things get complicated for Boston. If Gray walks away from the option, the Red Sox would still be on the hook for $10 million, and he could then test the market for a contract worth around $20 million per year.
Given his performance, that scenario is easy to imagine. Gray has posted a 2.76 ERA and a 17-5 record with the Red Sox in 2026, production that makes him attractive even with his age working against him.
The real problem for Boston is that Gray could do even better by leaving the option behind and landing a two-year, $40 million deal elsewhere. That kind of contract would give him another $20 million in 2028 no matter what happens in 2027.
So while the Red Sox would like to keep one of their best starters in place, they may be staring at a situation where Gray earns a bigger payday and Boston loses a key arm in the process. It’s a tricky one, and Craig Breslow will have to handle it carefully.
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