If Sonny Gray departs Boston this offseason, the Red Sox could find themselves staring at a familiar problem: where to turn for another right-handed starter.
The internal choices are there, but none comes without baggage. Brayan Bello, Tanner Houck and Kutter Crawford are all in the mix, yet each carries a question mark.
Bello was more effective in the bullpen in 2026 than he was in the rotation. Houck missed the entire season except for the regular season finale.
Crawford also sat out the entire season and has not appeared in a big league game since 2024.
Gray was excellent in 2026, but the expectation is that his expensive mutual option will be declined, sending him into free agency. Whether he comes back after that is anyone’s guess. If he does move on and Boston chooses to add outside help, three names stand out: Michael King, Freddy Peralta and Casey Mize.
King is already a known quantity around these parts. He was linked to the Red Sox last offseason before staying with the San Diego Padres, and he now has an opt-out waiting for him this winter after a strong 2026 season.
He posted a 3.21 ERA in 32 starts and set a career high with 4.3 wins above replacement. If he opts in, he’ll get a hefty raise for 2027 and then hold a player option for 2028.
If he heads to the market instead, he should be in line for something longer. At 31, and with Boston College on his resume, King would make plenty of sense as a top target if Gray leaves.
Peralta may be the best right-hander available. He turned in a 3.25 ERA in 10 starts with the Tampa Bay Rays after the trade deadline, then has followed that up with a 0.84 ERA in two playoff starts this fall.
For his postseason career, he owns a 3.48 ERA across 11 games. The catch is obvious: he’s likely to command a massive contract.
Mize brings a different profile. He worked to a 2.70 ERA in 16 starts with the Detroit Tigers before being traded to San Diego, where things went sideways.
With the Padres, he posted a 7.46 ERA in 10 starts. If Boston believes it can get him back to the version that thrived in Detroit, Mize could be a strong fit - and he likely wouldn’t cost nearly as much as Peralta.
In Other News...
Payton Tolle Is Giving Red Sox Fans A Classic New Debate
Payton Tolles mustache has become part of the conversation in Boston almost as much as his pitching. Nick Offerman, the actor and comedian, brought Tolle up on a podcast and joked that he could pass for the young Red Sox pitchers father, thanks to the matching facial hair. Tolle took the attention in stride and answered with a playful post on social media, which only added to the growing sense that he is quickly becoming one of the more distinctive figures in the clubhouse.
For Red Sox fans, the fun part is that this is not just about the look. Tolles pitching performance has helped make him a name worth following, and the mustache comparisons naturally invite a little nostalgia for the long line of Boston players who became icons for theirs. The debate now is less about whether Tolle fits the look and more about where he belongs in that Red Sox tradition, a question that seems likely to keep getting louder as he keeps taking the mound. [Read more 🡒]
Brewers Trade That Shocked Fans Looks Bigger Than Ever Now
When the Brewers shook up their roster ahead of the 2026 season, the deal that sent Caleb Durbin, Andruw Monasterio, Anthony Seigler and a draft pick to Boston drew plenty of attention, especially with Kyle Harrison, David Hamilton and Shane Drohan heading back to Milwaukee. For the Red Sox, it was the kind of move that immediately invites scrutiny, because it came alongside Milwaukees other headline trade sending Freddy Peralta to the Mets and set up a season in which both clubs would spend plenty of time being judged against the return.
David Hamilton, in particular, has made the trade look even louder in hindsight, with a key playoff role helping fuel Milwaukees run. Harrison and Drohan have also been part of the Brewers regular-season and postseason picture, which only adds to the intrigue for Boston as the organization weighs what it gave up and what it got back. For a front office that has to think about both now and the years ahead, this is the sort of swap that can linger well beyond the first round of reaction. [Read more 🡒]
Caleb Durbin Admits One Tough Feeling Watching Brewers Reach World Series
Caleb Durbin spent part of the postseason watching the team that once had him in its plans keep rolling all the way to the World Series, and it naturally stirred up some mixed emotions. Traded from the Brewers to the Red Sox in February, Durbin had to see Milwaukee sweep the Dodgers while Bostons season ended in the Wild Card Series, a reminder of how quickly one clubs October can become another players what-if.
Even so, Durbin has made clear he feels good about where he landed. The move to Boston gave him a fresh start, and while Milwaukees run had to hit a nerve, he sounded comfortable balancing that old connection with his current situation. For a player trying to settle in with a new team, it was the sort of moment that can feel personal without changing the reality of where he is now. [Read more 🡒]