The Red Sox found themselves in a good problem last offseason: they needed a No. 2 starter, and they got one who has looked more like the anchor of the staff.
Boston’s trade for Sonny Gray was met with some skepticism at the time, mostly because plenty of people figured he fit better somewhere lower in a rotation than in the role of a contender’s second starter. Gray has answered that noise in a big way.
He has been Boston’s best starter all season, and now he’s lined up to draw Cy Young Award votes. If the Red Sox want to keep that going past 2026, they’re going to have to pay for it.
MassLive.com’s Chris Cotillo reported that some around the industry believe Gray could land a contract in the neighborhood of three years and $75 million, or more, if he keeps pitching like this. Cotillo also noted that Gray has not committed to pitching again in 2027. In a recent interview with The Boston Globe, Gray said he would retire “in a heartbeat” if his family signaled that he was wanted back home year-round, even if that meant retiring after the end of this year.
That same three-year, $75 million figure is already familiar territory for Gray. It’s the deal the Cardinals gave him before the 2024 season, and it’s the contract he’s now finishing.
After this year, he has a $30 million mutual option for 2027 with a $10 million buyout. If Boston picks up its side of the buyout and Gray opts out, the buyout would be forfeited.
The numbers this season make the case pretty clearly. Gray is 17-5 with a 2.76 ERA and 4.0 wins above replacement across 156 2/3 innings.
At 36, he’s in the part of his career where teams usually start thinking twice. Gray hasn’t given anyone a reason to do that yet.
And the market for pitching keeps climbing. Cotillo pointed out that a deal with a $25 million annual value would put Gray in the range of pitchers like Michael King, Sean Manaea and Nathan Eovaldi, while sitting just above Aaron Nola, Seth Lugo, Robbie Ray and Luis Severino. Gray has been better than all of them so far this season.
Boston’s situation makes the decision even more straightforward. The organization doesn’t have nearly the same amount of minor league pitching depth it once did after trading away Hunter Dobbins, Richard Fitts, Brandon Clarke, Anthony Eyanson, Kyson Witherspoon and Connelly Early over the last year.
Looking ahead to 2027, Garrett Crochet, Payton Tolle, Ranger Suárez and Jake Bennett are locks for the rotation. Johan Oviedo could factor in, and Tanner Houck could as well.
But the season has already shown how quickly injuries can change everything. You can never have enough arms.
That’s why a dependable veteran like Gray makes sense for the next few years. There’s no certainty he’ll still be pitching after 2026, but if he is, Boston should be the team he’s doing it for.
In Other News...
Red Sox Trade Is Starting To Look More Complicated Than Fans Thought
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For the Red Sox, that shifting value matters because this was never just about one headliner. The deal also sent and brought back other players and prospects, and the early returns are making it harder to judge what Boston really got out of the exchange. Some pieces have shown promise, others are still too young to read cleanly, and the longer Durbin keeps trending up, the more this trade starts to feel like one the Red Sox will be measured against for a while. [Read more 🡒]
Red Sox Prospect Franklin Arias Is Giving Fans A Bigger Question
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What makes Arias especially interesting is the company he now keeps in conversations about Venezuelan baseball, a pipeline that has produced stars such as Miguel Cabrera and Ronald Acua Jr. With a full list of top prospects from the country turning heads, the bigger question for Boston is no longer whether Arias belongs on the radar, but how high he can climb from here. [Read more 🡒]
Red Sox Face A Tough Garrett Whitlock Decision Again
Garrett Whitlock is once again at the center of a familiar Red Sox conversation, one that blends roster need with role uncertainty. He came up as a reliever, has logged some starts along the way, and has said he is open to moving back into the rotation if that is what Boston needs. For a club with limited right-handed starting options, that makes him an obvious name to keep in mind.
The appeal is easy to see, but so is the caution. Whitlock has had more success in relief, and injuries have complicated his ability to hold down a starting job for long stretches. So even with the rotation picture giving Boston reasons to consider the idea, the Red Sox are still left weighing whether the upside of stretching him out is worth the risk of losing what he already does so well. [Read more 🡒]