Which Impending Free Agents Should the Red Sox Attempt to Re-Sign?

The Boston Red Sox's season is over, meaning it's time for offseason prep work to begin. Though you can be sure the front office has been scouting and researching players due to be available this winter for years, it's only now that the full efforts of the team's braintrust can be focused on improving the roster for 2026.

The quickest work the team can do is approach each of their impending free agents. This year, the Red Sox have four: Steven Matz, Dustin May, Justin Wilson, and Rob Refsnyder. The former two were the lone trade deadline acquisitions this past July, while the latter pair are important veteran leaders in the bullpen and on the bench, respectively. It'll be interesting to see how Boston handles their respective trips to free agency, especially with pivotal option decisions looming for Lucas Giolito and Alex Bregman.

Unlike last year, when the Red Sox extended a qualifying offer to Nick Pivetta, I don't expect any of these four players to receive a QO from the team. None of them will approach a deal with the $22 million AAV the qualifying offer is worth this year, and most (if not all) will have to accept a short-term contract, either to rebuild value or because of their age. 

Though they don't apply for this article, it is worth keeping in mind that more than $32 million will be removed from the payroll this offseason now that the dead money for Eric Hosmer, Walker Buehler, Abraham Toro, and Michael Fulmer is finally coming off the books. That's real money that can now be used on the active roster, and perhaps in the re-signing of the following players.

Note: This article only covers players who are due to be free agents during the 2025-26 offseason. All players with options (team/player/mutual) will be covered in a separate article.

Steven Matz

Let's start with the player the Red Sox are most likely to re-sign among this crop. Matz was really good after being scooped up at the trade deadline, posting a 2.08 ERA in 21 2/3 innings once arriving in Boston. He became the preferred middle-innings southpaw option for Alex Cora, and it's telling that he made it into two of the team's three playoff games against the Yankees.

Now 34 years old, it's worth pointing out that Matz's peripherals weren't as sterling as his actual results with the Red Sox. His 4.20 xERA and 4.84 FIP both spoke to his troubling home run issues and declining strikeout rate, though he's still a reliable lefty specialist who rarely walks anyone. With Wilson also slated to be a free agent, Brennan Bernardino is the only left-handed option projected to be in next year's Opening Day bullpen besides closer Aroldis Chapman. This is probably a keep-one-or-the-other situation, and if Matz is willing to accept a short-term deal at his previous AAV ($11 million), there's a good chance he comes back to the Red Sox.

Dustin May

May's tenure in Boston did not go according to plan, as he pitched just 28 1/3 innings with the Red Sox before landing back on the injured list with elbow neuritis. He was throwing by the end of the year, though the team didn't activate him before the playoffs. Though he dazzled a few times, his 5.40 ERA, 5.39 FIP, 19.5% strikeout rate, and 1.69 WHIP were enough to know that for all of his potential, May simply isn't consistent enough to rely on every fifth day anymore.

I said back at the trade deadline that the trade for May could still work out in Boston's favor if they re-signed him, though that may no longer be the case. The Red Sox have had a recent affinity for signing injured pitchers to multi-year deals -- Lucas Giolito, Patrick Sandoval, and Liam Hendricks come to mind -- but they already have the information they need on May. If they do bring him back, it'll be on a very low-risk deal.

Justin Wilson

Wilson has been around the block, having pitched for seven teams over his 13-year career. Notably, he's never lasted more than three years with any franchise, though he's always made it at least two before leaving (at least prior to joining the Red Sox in 2025). The veteran southpaw was a valuable addition to the bullpen this year, recording a 3.35 ERA, 2.95 FIP, and 27.5% strikeout rate in just shy of 50 innings. He wasn't used as a lefty specialist, though as expected, he was far better against hitters of the same-handedness (.212/.292/.282 slash allowed to left-handed batters; .306/.382/.439 slash allowed to right-handed batters).

There's no reason not to want Wilson back next year, especially if he's willing to take another cheap one-year deal (his 2025 salary was just $2.25 million), but as mentioned with Matz, there's only so much room for old left-handed relievers in this bullpen. At 38 years old, Wilson is close to the end of his career and he may prioritize one more shot a World Series ring; his chances of re-signing may come down to his belief in the 2026 Red Sox's championship chances.

Rob Refsnyder

Like most Red Sox fans, I'm a big Rob Refsnyder guy, as he continues to just simply excel at the role that has been laid out before him. His overall batting line of .269/.354/.484 (128 wRC+) was impressive enough, and those numbers exploded to .302/.399/.560 (159 wRC+) against left-handed pitchers. His walk rate practically doubled against southpaws, and he dropped his strikeout rate by nearly eight percent. It was the third time in four years since he arrived in Boston that Refsnyder posted a wRC+ above 150 against lefties.

Of course, Refsnyder was considering retirement just last offseason, and the conversation could still be on the table. He probably deserves a raise over his 2025 salary of $2.1 million, though at 35 years old (on Opening Day 2026) and with Romy Gonzalez featuring in a very similar role, Refsnyder may be gearing up to move on, be it to another team or to the next phase of his life.