Justin Wilson was one of the best surprises for the 2025 Boston Red Sox after being picked up off the scrapheap in free agency. He recorded a 3.35 ERA, 2.95 FIP, and 27.5% strikeout rate as the most reliable southpaw in the bullpen not named Aroldis Chapman.
At 37 years old, he proved that he still had the goods to pitch in a high-leverage role, ranking in the 91st percentile in whiff rate (31.9%) and the 82nd percentile in strikeout rate. By all accounts, the Red Sox should want him back in their bullpen mix in 2026.
Yet, despite that success, Ken Rosenthal and Will Sammon of The Athletic report that "It is unlikely Wilson, 38, pitches in 2026 unless it is on a fair deal with a legitimate World Series contender."
After a 13-year career in the big leagues, Wilson has earned the right to go out on his own terms if he chooses. And yet... that description fits the Red Sox to a tee, doesn't it?
Justin Wilson is reportedly considering retirement after a strong 2025 in Boston.https://t.co/yNlVZgYa4B
— Chris Cotillo (@ChrisCotillo) January 7, 2026
Red Sox, Justin Wilson should have mutual interest in 2026 reunion
Deploying Chapman, who will also turn 38 at the end of February, and Wilson as the two highest-leverage southpaws in the bullpen is probably a plan rife with pitfalls. Both pitchers were excellent last year, but eventually, Father Time catches up with everyone.
But that's more of a long-term concern than a short-term one. Even if both relievers regress from last year's form, they'd still be a formidable duo to build around in the late innings.
In terms of Wilson's two requirements to return, the Red Sox are clearly "legitimate World Series contenders." Their starting rotation has been heavily beefed up with the additions of Sonny Gray and Johan Oviedo, and if they can add Bo Bichette or Alex Bregman to the same infield now led by Willson Contreras, there's a good chance they'll enter the 2026 season as one of the favorites to win the American League pennant.
The money shouldn't be a problem either; Wilson earned just $2.25 million in 2025. Boston's payroll is still about $16 million shy of last year's end-of-year figure, so giving the veteran southpaw a notable raise on a one-year deal shouldn't hurt their bottom line in any noticeable way.
Lastly, he would be guaranteed a key role in the bullpen if he does choose to return. With Steven Matz leaving for the Tampa Bay Rays in free agency and Chris Murphy and Brennan Bernardino being traded away, the only lefties in the relief corps are Chapman and Jovani Morán. Wilson would patch a huge hole if he comes back.
As such, there should be ample motivation from both sides to get a deal done. Wilson has never advanced past the League Championship Series in his long career, and the Red Sox need another southpaw to deploy in the late innings. Sometimes, it really is this simple.