Sonny Gray free agency suitors that could steal veteran from the Red Sox

After hinting at a potential retirement ahead of the postseason, Boston Red Sox pitcher Sonny Gray has the first decision on his future. Gray, who turns 37 next month, told the Boston Globe that he intends to pitch in 2027. The veteran righty enjoyed a renaissance season in Boston, finishing 18-5 with a 2.72 ERA — his best since becoming a full-time starter in 2014 — and 4.3 bWAR over 29 starts.

“My family and I have talked about it, and it’s an easy decision,” Gray said. “I still want to win a World Series, whether that is [with] Boston or with whoever wants me.”

As for Gray’s future in Beantown, the Red Sox hold a $30 million mutual option with a $10 million buyout. Things might get awkward, though, given that he took jabs at manager Chad Tracy and the organization’s overall philosophy after the Wild Card Series; Tracy pulled Gray early in the season-ending wild card loss to the rival Yankees, even though Gray had done extremely well facing that lineup for a third time. 

Assuming that the mutual option doesn't go through, let’s look at some possible realistic landing spots. In other words, you shouldn’t plan to see him sign with the Rockies or Angels. 

Chicago Cubs

Gray makes way too much sense for the Cubs, who have multiple starting pitchers slated to hit the open market. Matthew Boyd and David Peterson are pending free agents, and Clay Holmes has a $12 million player option. It’s hard to envision all three returning, especially if Holmes believes he can cash in before the likely work stoppage.

We’re all for retaining Shota Imanaga and Kevin Gausman, but both pitchers are ineligible for the qualifying offer. All signs point to the QO being roughly $23.1 million, and we’ll see whether either comes anywhere close to receiving that much in total compensation. Things could get very interesting on the North Side this winter.

Chicago White Sox

Arguably the greatest takeaway from the White Sox’s playoff run is their desperate need for a proven No. 1 starter. That’s admittedly a lot to ask of a 37-year-old pitcher, especially one with as much mileage as Gray. So it comes down to a vital question: are you paying Gray to be an ace, or do you need a reliable starter who fits better as a No. 3? 

Given how competitive the AL Central should be next season, we suggest the South Siders pursue him either way. He’s pitched at least 166 innings each of the last four years, and Sean Burke was the only White Sox pitcher to exceed that total this year. 

Detroit Tigers

You’ll probably see the Tigers frequently appear on these lists, and for good reason. Speculation is mounting about Tarik Skubal returning to Detroit, and we’ve also pitched embattled Yankees second baseman Jazz Chisholm Jr. as an ideal free-agent addition. Don’t be surprised to see further aggressiveness from a team coming off an incredibly disappointing 2026 campaign.

Good news for Tigers fans: Gray owns a 2.33 ERA over 27 innings in five starts at Comerica Park — er, Fifth Third Park. 

Miami Marlins OR Washington Nationals

We’re looping these teams together because they’re in extremely similar situations. Both the Marlins and Nationals stayed in the playoff hunt deep into the second half, and the NL East could be far more competitive than people might expect. (That’s assuming, of course, that there is an NL East title to contend for next year, but you get our point.)

Objectively, the Nationals are probably a better fit from a rotation standpoint, but the Marlins might be closer to competing for a division title. But here’s a fun fact: Gray has a 5.00 ERA in 10 starts against the Nationals, but a 2.89 ERA in eight starts against the Marlins.

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