The Boston Red Sox have a core that may be on the rise, but certain factors still hold the team back from becoming a legitimate contender in October. This includes another high-leverage reliever. With the arms on the market this winter and the model of elite late-game relief proving decisive, the Red Sox should frame this offseason around building what one recent analysis called a "super-bullpen", per Ken Rosenthal on The Athletic.
Boston already has the dominant veteran flame-thrower Aroldis Chapman locked in for 2026, but the aging closer model means Boston must think long-term now. According to Rosenthal, the Red Sox don't want to outright replace Chapman, but "give them a potential long-term replacement" when he eventually hangs up his cleats. In the meantime, it's all about building the best 2026 bullpen possible this winter.
Fortunately, the Red Sox won't see a shortage of potential names to target.
Red Sox Need These 4 Relievers in the 2026 Bullpen
As the MLB free agency period approaches with each passing day, enter these four relievers the Red Sox must have their eyes on: Devin Williams, Edwin Diaz, Ryan Helsley, and Raisel Iglesias.
Williams remains a compelling asset despite a down year, posting a 4.79 ERA with the New York Yankees and getting demoted from the closer role. Regardless of this, his signature change-up and postseason experience make him an intriguing fit. At his best, he's a lights-out pitcher, and if anybody can make him better, it's Andrew Bailey, the Red Sox pitching coach who actually fits well with his repertoire and pitching tendencies.
Interestingly enough, Rosenthal recently reported that the Red Sox "have shown interest" in the Yankees' pending free agent, leaving time to tell if that interest will result in pen being put to paper.
Meanwhile, Diaz is arguably the gold standard of modern closers. If Boston can land him, it would send a signal that not only are they all-in, but they will start a butterfly effect, where other players will see what the Red Sox are doing and will want to play in Boston. He's a three-time All-Star who's racked up 253 saves in 520 relief appearances.
Meanwhile, Helsley and Iglesias both offer strikeout stuff and multi-year potential in the back end, fitting the vision of a bullpen built for longevity. Helsley could be an affordable option as he's coming off his worst ERA (4.50) since the 2021 season. As for Iglesias, he'd be a reliable arm after tallying 29 saves in a National League-leading 57 relief outings in 2025.
Red Sox Need Bullpen Help More Than Ever
Why now? Because the modern playoff landscape rewards teams that can shut games down late. Just look at the World Series this year, where both the Los Angeles Dodgers and Toronto Blue Jays battled with their endless pitching staff. The key to this series wasn't Miguel Rojas or Jeff Hoffman; it was the Dodgers' pitching depth. That's how they were able to repeat as champions this year.
The Red Sox have invested heavily in position players and rotation pieces, yet still fell short. The difference often comes down to three-inning stretches in October when bullpens are put to the test. Boston has the means this offseason, both in payroll flexibility and roster gaps, to swing for something special.
If the Red Sox make a move, the bullpen could be the best since 2017 or even 2007. They must stop treating the bullpen as a secondary objective, and Chiefs Baseball Officer Craig Breslow seems like he knows this as well.
With getting one of these four arms, the Red Sox have the chance to build their version of said super bullpen and finally flip a late-season disadvantage into a competitive edge.