Oct 8, 2025; Chicago, Illinois, USA; Chicago Cubs pitcher Brad Keller (40) celebrates after defeating the Milwaukee Brewers in game three of the NLDS round for the 2025 MLB playoffs at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images Matt Marton-Imagn Images

Cubs Reliever Could be Perfect Fit for Yankees

Originally posted on New York Yankees on SI
By Erin Shapland | Last updated Nov 7, 2025 9:00 AM ET

The New York Yankees are beginning to make their offseason moves, and pitching is one of their top priorities as they look to shore up a hurting bullpen. A Chicago Cubs free agent could be a perfect match for their needs, given a strong breakout season in 2025.

Brad Keller, a right-handed reliever for the Cubs, earned a stunning 2.07 ERA in 68 games (with one start) in 2025. He is proving to be a strong bullpen option after falling short as a starter, and could be a strong option for the Yankees.

On their list of the top 50 free agents this offseason, the Athletic named the Yankees as one of the strongest fits for Keller (with a return to the Cubs and a move to the Texas Rangers), describing him as a strong option if he can repeat his success.

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"After seven years struggling to find consistency with a 4.33 ERA as a starter, Keller made the full-time switch to the bullpen and thrived," the Athletic's Aaron Gleeman wrote. "Compared to his time as a starter, Keller boosted his strikeout rate, cut his walks and added 3 mph to his fastball."

"Now it’s just a question of how much faith the league has in his age-29 breakthrough being sustainable, because he certainly pitched like a high-end setup man for the Cubs in 2025."

Yankees' Offseason Pitching Moves So Far

So far, the Yankees have brought reliever Tim Hill back, exercising his $3 million club option, and parted ways with reliever Jonathan Loaisiga, predictably, after an underwhelming 2025. Loaisiga had been in pinstripes since 2018. Relief pitchers Devin Williams and Luke Weaver are now free agents, and pose major questions as the Yankees consider which reunions are worthwhile. Williams in particular struggled in his first season in New York, but recovered well in the fall and late summer, and shared that he would be open to another season with the Yankees when all was said and done.

When they announced their $22 million qualifying offer to free agent center fielder Trent Grisham, the Yankees also announced that they had added right-handed pitcher Kervin Castro to the 40-man roster.

Yankees Need Bullpen Depth

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The Yankees are faced with some tough offseason decisions about how to support current closer David Bednar, fellow relievers Camilo Doval and Fernando Cruz and their remarkably strong starting rotation. Though several are hurt at the moment, when they are back to full health (ideally by the summer), the Yankees will have Gerrit Cole, Carlos Rodon, Clarke Schmidt and currently-healthy starters Max Fried, Cam Schlittler, Luis Gil and Will Warren.

The Yankees suffered some sloppy losses in 2025 due to defensive errors and blown saves, so a strong bullpen is considered a main offseason priority, in addition to their major questions in the outfield.

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