The Chicago Cubs have quite a few free agents after a successful 2025 season. While Kyle Tucker is perhaps the most lucrative catch in the open market this winter, the Cubs’ bullpen needs some attention.
Names like Brad Keller, Caleb Thielbar, and Drew Pomeranz are all looking for their next deal. And Chicago will have some negotiating to do should any of its free agent relief pitchers garner a bigger deal than the one the team is prepared to make.
In case any of those players, among others, walk in free agency, Chicago already added veteran relief pitcher Phil Maton. While he may not be the best addition the Cubs could have signed, he is a viable option for a bullpen that needs a retool for 2026.
Here is a look at a trio of relief pitchers that Chicago should keep in their bullpen.
Brad Keller
Chicago Cubs pitcher Brad Keller | Matt Marton-Imagn Images
One of the top free agent relief pitchers this winter is the Cubs’ own. Keller had an impressive 2025 season, making him one of the more coveted arms for other teams’ bullpens.
After six seasons with the Kansas City Royals, Keller played for both the Chicago White Sox and the Boston Red Sox in 2024. He left the American League for the first time in his career and joined the Cubs on a one-year deal.
In 68 appearances, Keller pitched 69.2 innings and struck out 75 batters. He recorded three saves but also blew just as many. His 2.07 ERA was a major reason why the 30-year-old recorded 25 holds in relief.
BIG out from Brad Keller. 👏 pic.twitter.com/GPGx3AoOIn
— Chicago Cubs (@Cubs) October 9, 2025
Chicago would be wise to bring Keller back. However, the Cubs will face stiff competition for the free agent relief pitcher’s services in 2026 and beyond. However, if the team isn’t willing to match outside offers, Keller could be playing against the Cubs instead of for them next season.
Caleb Thielbar
Just like Keller, Thielbar spent the majority of his MLB career playing in the AL Central before joining the Cubs. The 28-year-old played eight seasons for the Minnesota Twins before coming to NL and Chicago.
Chicago Cubs pitcher Caleb Thielbar (24) pitches against the Tampa Bay Rays during a game at Wrigley Field. | Patrick Gorski-Imagn Images
In 67 games, Thielbar logged 58 innings and struck out 56 batters along the way. His ERA was slightly higher than Keller’s, but still effective at 2.64 in 2025.
Thielbar recorded a WHIP of 0.88 this past season, even better than Keller’s 0.96 for the Cubs. Both free agent pitchers helped their team end a four-year absence from the MLB Playoffs.
With the Northfield, Minnesota native being younger, Thielbar could be favored to return to Chicago compared to Keller, who might command more money on the open market this winter.
Drew Pomeranz
Chicago Cubs pitcher Drew Pomeranz | Benny Sieu-Imagn Images
Hailing from Memphis, Tennessee, this relief pitcher made a career revival in 2025 with the Cubs. After a four-season hiatus, Pomeranz saw his former team, the San Diego Padres, exit the playoffs during the NL Wild Card Round.
Recently turning 27, the veteran arm would be an asset for Chicago in 2026. If either Keller or Thielbar doesn’t return to the Cubs for next season, Pomeranz will be a major priority to sign.
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Pomeranz appeared in more games for Chicago than he did in his two years with San Diego. The left-hander posted an ERA of 2.17, and though it was higher than his two seasons (2020 & 2021) with the Padres, Pomeranz’s ERA was better than any other season before that.
Chicago would be wise to add him to another team-friendly one-year deal to maintain a level of consistency for their bullpen in 2026. Pomeranz is likely to come back as he may not get as many bites during free agency as Keller or Thielbar.
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