The buzz surrounding the starting pitching market is centered around Tarik Skubal and Freddy Peralta, and rightfully so. Both are in line for contracts in excess of $100 million, and in Skubal’s case, likely the largest for a starting pitcher in MLB history.
But a name to watch is Sonny Gray.
Gray, 36, is a free agent after declining his half of a mutual option with the Boston Red Sox. He’s someone that, even after 14 seasons, remains an impact starter. He posted a 2.72 ERA in 29 starts with Boston this year. He’s pitched at least 166.1 innings in each of the last four seasons. And he hasn’t posted a FIP above 3.99 since 2018.
If Gray decides to play this season, and he did indicate after the season that he intends to pitch in 2027, then there should be a long list of teams gunning for his services. And with a return to the Red Sox reportedly unlikely, let’s look at some fits for the veteran right-hander.
St. Louis Cardinals
Gray has pitched with St. Louis before. Why not return to a place that he loved?
The Cardinals are an emerging young team. They have emerging stars in JJ Wetherholt and Jordan Walker, and a roster that is close to competing. What they should not do is sign free agents to long-term contracts, instead aiming for short-term deals that leave the future books open. That’s precisely what Gray is.
The Cardinals traded Gray to the Red Sox after the 2025 season. He knows manager Oli Marmol. He’s familiar with the young stars. And in two seasons with the team, he posted a 4.07 ERA in 60 starts. Adding him to headline the rotation and fight to get into the postseason makes all the sense for Chaim Bloom and the front office, which should have money to spend this winter.
Chicago Cubs
When I think of the Chicago Cubs’ offseason plans, I think of pitching, pitching, figuring out what to do with Ian Happ and Seiya Suzuki, and pitching.
It feels like this has been a problem for the Cubs for years because, really, it has been. They traded for Kevin Gausman and Clay Holmes at the deadline. It didn’t fix the problem. A return for Holmes should not be ruled out and even if the Cubs did re-sign the right-hander, they need more help. And that’s where Gray comes in.
Gray would be an excellent fit atop the rotation and give them a strong, dependable veteran who they can count on in big games. The fact he will only require a short-term contract should also be appealing. They splurged last winter for Alex Bregman, and they should do it here with another former Red Sox star.
Atlanta Braves
There was buzz last offseason that the Atlanta Braves could sign an impact starter. It did not happen. There was buzz at the last trade deadline that the Braves could add an impact starter. They ended up with Tyler Mahle (which worked wonderfully) but did not land the star that many craved.
Gray would be an excellent fit and finally fulfill the prophecy of Gray to Atlanta that has been speculated for years. The Braves have options, though, and could try another run at acquiring Jacob deGrom from the Texas Rangers. Skubal is a free agent and would be an excellent fit, but Alex Anthopoulos is not typically involved with contracts of that magnitude.
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