Will the Boston Red Sox and three-time All-Star Sonny Gray find a way back together in free agency this winter?

Until the day he signs on the dotted line elsewhere, there is at least a chance. But the odds may not be in Boston's favor. On Thursday, WEEI's Rob Bradford was asked about the chances of Gray coming back to town and didn't rule it out, but he certainly didn't sound confident about the idea with the price tag being the biggest factor.

"I think he's going to get some money as a free agent now," Bradford said. "I don't buy that he'll go anywhere for the money. I think he is firmly dug in that there are places that he'd go with his family. I don't think he's ruling out the Red Sox. The problem is that with guys like that, the Red Sox might say, 'Hey, if you're not going to come at our price, we are going to get someone else at a lower price.' ...

"I wouldn't rule out Sonny Gray, but I'm not optimistic about Sonny Gray."

What To Do With Sonny Gray

Gray was great in 2026. There were few pitchers in general who had as good a season as the righty did. Gray led the league with 18 wins and pitched to a 2.72 ERA and a 149-to-46 strikeout-to-walk ratio in 169 innings pitched in his first season in Boston.

The Red Sox acquired Gray from the St. Louis Cardinals ahead of the campaign and he took his game to another level. In 2025, Gray had a 4.28 ERA and a 201-to-38 strikeout-to-walk ratio in 180 2/3 innings pitched. The ERA number specifically gave some in the Red Sox's fanbase pause when Boston swung the deal last offseason. But he outperformed all expectations.

Now, he's in line to land another multi-year deal and he should cash in. Spotrac has his market value projected to be just over $58 million over three seasons.The Athletic projected Gray's ultimate contract to fall closer to a range of $55 million over two seasons. Spotrac's projection has a $19.33 million annual average. The Athletic has an annual average of $27.5 million. When it comes to the Spotrac number, the annual average is perfectly fair, but it would be three seasons, which would include his age-39 campaign. The Athletic's projection arguably would be too much on an annual basis, but at least it wouldn't be very long.

ESPN projected that Gray will land a deal in the range of $42 million over two years. That's more like it. Arguably, that's a perfectly fair deal and would make a lot of sense for Boston. If he ends up landing a two-year deal with a $21 million annual average that should be the type of value that Boston would consider bringing back.

The grass isn't always greener elsewhere. There will be a handful of intriguing hurlers available, but everyone has success in Boston. Gray has proven that he can. If his deal ends up falling in the range that ESPN projected, Boston should bring him back. The Athletic's projection arguably is too high. Spotrac's is a great annual value, but three years would be long.