Arguably the best-available left-handed reliever is reportedly thinking about signing with no one this offseason.
Justin Wilson, a lefty specialist who spent 2025 with the Boston Red Sox, is reportedly considering retiring unless he can latch on with a team that is a “legitimate World Series contender” according to The Athletic.
Wilson went 4-1 with a 3.35 ERA and 57 strikeouts in 48 1/3 innings for Boston in the regular season while pitching on a one-year, $2.25 million contract. He has a 38-30 record and 3.59 career ERA over 648 appearances in 13 seasons with the Red Sox and six other big-league teams.
Justin Wilson Wants To Win A World Series
Most lefty relievers like Wilson can continue to pitch until they simply don’t want to any longer, especially since the veteran is effective against both lefties and right-handed hitters. Wilson has allowed a lower OPS to righties (.663) than lefties (.689) in his decade-plus career, though right-handed hitters slashed .306/.382/.439 off Wilson in 2025.
Still, any team could use an effective left-hander out of his bullpen. But according to the duo of Ken Rosenthal and Will Sammon, Wilson has one last accomplishment to achieve before he potentially hangs up his glove.
“Veteran pitcher Justin Wilson, perhaps the best lefty reliever available in free agency, is considering retirement, league sources said,” The Athletic insiders reported Wednesday. “It is unlikely Wilson, 38, pitches in 2026 unless it is on a fair deal with a legitimate World Series contender.
“One major accomplishment that has eluded Wilson — who starred in the College World Series for winner Fresno State in 2008 — is a World Series ring.”
Wilson is a Southern California native, from Anaheim, and his people may be signaling the Los Angeles Dodgers to sign him for 2026. The Dodgers drafted him in the 37th round of the 2005 MLB Draft before he went to Fresno State and was chosen by the Pittsburgh Pirates in the fifth round of the 2008 draft.
The Red Sox Could Bring Justin Wilson Back Midseason
If the Dodgers don’t take the hint, the Red Sox could opt to keep Wilson on the back burner until after spring training or the regular season starts.
Boston does not have a left-handed reliever on its roster outside of closer Aroldis Chapman but may want to give Payton Tolle or Patrick Sandoval the chance to earn a high-leverage spot.
If neither does, or either sustains an injury at some point, the Red Sox could always sign Wilson to a cheap, prorated deal. Boston, after all, made the playoffs in 2025 and have improved its roster already with still two-and-a-half months until the season starts.
But if the Red Sox wait, they could open the door for a different contender like the New York Mets, Toronto Blue Jays or New York Yankees could also get in the mix.
Wilson has pitched two tours with the Yankees and was a member of the Mets, Chicago Cubs, Detroit Tigers and Cincinnati Reds, each of whom was a playoff team in 2025 or considers itself a contender in 2026.
There’s always the potential for a low-risk, prorated deal that gets inked midseason. Wilson may not want to make 60-plus appearances, which he has done in consecutive seasons for the Reds and Red Sox, but is still a useful bullpen arm for most major-league teams.
Red Sox Free Agent Reliever Might Retire From Baseball, Insiders Reveal