Chicago Cubs favored to retain two key free agents, per insider

The Chicago Cubs will have to make some big decisions this offseason, ahead of a 2026 where the team hopes to improve upon a promising 2025.

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Finding a way to keep free agent right fielder Kyle Tucker is probably the most headline-friendly issue facing the team right now. The Cubs will have to decide on picking up their option on pitcher Shota Imanaga. Rumors have also been floated regarding the possibility of picking up a high-end starting pitcher like Dylan Cease.

But maybe the toughest task facing Chicago will be in almost completely reassembling the team’s bullpen.

Rebuilding the Chicago Cubs bullpen

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As things stand right now, six of the eight relievers on the NLDS roster may be gone by next season, with non-roster arms Ryan Brasier and Taylor Rogers also likely to be lost to free agency.

That means the Cubs will have to build around the last bullpen asset Daniel Palencia while hoping for the best from struggling pitchers like Ben Brown, Porter Hodge, Eli Morgan, and Jordan Wicks.

The loss of Brad Keller, Drew Pomeranz, and Caleb Thielbar will hit especially hard as the trio finished the year as the anchors of manager Craig Counsell’s pieced-together bullpen.

MLB insider on the fates of two free agent Cubs

Jim Bowden, a former MLB exec now working as an MLB insider for The Athletic, however, believes that at least Keller and Pomeranz have a good chance of remaining a Cub.

Bowden lists the Cubs as the best fit when it comes to picking up the contracts of both Keller and Pomeranz when the pair become eligible for free agency after the World Series.

Per Bowden:

Brad Keller

After a career spent mostly in the rotation with Kansas City, Keller made 14 of his 16 appearances in 2024 out of the bullpen, splitting the season between the White Sox and Red Sox. This year, he was in the bullpen full-time after joining the Cubs. He embraced the role, appearing in 68 games and posting an impressive 2.94 FIP, while being an integral part of the Cubs’ bullpen success. He’s set himself up for a bright future as a high-leverage reliever.

Drew Pomeranz

After beginning the season in the Mariners’ farm system, Pomeranz was traded to the Cubs for cash in April. He then was promoted to the big leagues and appeared in 57 games for Chicago, posting a 3.01 FIP with 10.5 K/9 and an ERA+ of 178. He made six appearances for the Cubs in the postseason, allowing one run in six innings. This season was his first pitching in the big leagues since 2021. His fastball run value ranked in the 85th percentile and his strikeout percentage was in the 84th percentile. Batters hit just .207 against his four-seam fastball and .220 against his knuckle curveball.

Keller and Pomeranz as “must keep” success stories

The career comebacks of both Keller and Pomeranz are tremendous stories.

Keller was a non-roster invitee to Cubs’ spring training after a failed multi-year run with the Royals, Red Sox, and White Sox. He finished 2025 with a 2.07 ERA in 68 appearances, eventually working his way into Counsell’s circle of trust to become a high-leverage bullpen asset.

Pomeranz, meanwhile, was all but out of baseball entirely before he got one last chance with the Cubs in 2025. He hadn’t pitched in the majors since 2021 and seemed bound for forced retirement. He ended the 2025 campaign with a 2.17 ERA in 57 appearances.

Bowden is estimating Keller’s contract as 2-years for $15 million and Pomeranz’s as 1-year for $5 million.

History shows, however, that the Cubs are not receptive to re-signing bullpen arms, even after stellar breakthrough seasons. They generally shy away from any even marginally lucrative deals for relievers, especially middle relievers. This front office’s strategy has always been to bargain hunt for bullpen arms and fill up the roster with cheap rehabilitation projects in hopes that one or two or three will stick.

But in this case, staring down so much turnover, it would be wise to maybe buck their standard operating procedure and bring both Keller and Pomeranz back on short-term deals. This team needs a stable bullpen.

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Source: https://www.chicitysports.com/chicago-cubs-free-agents-2026-keller-pomeranz