The Chicago Cubs enter the offseason with several key members of their bullpen hitting free agency. Left-handed pitchers Taylor Rogers, Caleb Thielbar, and Drew Pomeranz are all free agents, along with right-handers Brad Keller, Ryan Brasier, Michael Soroka, and Aaron Civale. Furthermore, the team traded Andrew Kittredge back to Baltimore, who had previously sent him packing to Chicago at last summer’s trade deadline.
With eight relievers departing, seven via free agency, the Cubs’ front office faces the challenge of reshaping the bullpen this offseason. Bullpen turnover is nothing new in baseball, and after a strong 2025 campaign, several of Chicago’s relievers are expected to seek bigger paydays elsewhere, likely ruling out a reunion.
Still, not everyone will price themselves out of the Cubs’ plans. Here’s a look at the relievers who stand the best chance of returning to Wrigley Field in 2026.
Which Chicago Cubs free agent relievers are most likely to return in 2026?
Sep 7, 2025; Chicago, Illinois, USA; Chicago Cubs pitcher Drew Pomeranz (45) throws the ball against the Washington Nationals during the first inning at Wrigley Field. Mandatory Credit: David Banks-Imagn Images
The first name that comes to mind is Pomeranz. Set to turn 37 next season, he was given an opportunity in 2025 to reunite with Craig Counsell in Chicago. After not appearing in the majors since 2021, he made the most of it. Pomeranz posted a stellar 2.17 ERA across 49.2 innings, proving he still has plenty left in the tank. Having already earned over $50 million in his career, it’s plausible he’d be open to returning on a modest one-year deal.
Similarly, Thielbar could be a candidate to return in 2026. The veteran left-hander will be 39 by the time Spring Training arrives and is coming off a career year with the Cubs. In 2025, he posted a 2.64 ERA over 58.0 innings, his best ERA mark in a single season, aside from the shortened 2020 campaign. Chicago might need to offer a modest raise from the $2.75 million he earned last year, but it wouldn’t take a significant increase to bring him back.
On the other hand, Keller appears to be a long shot to return in 2026. He also enjoyed a breakout 2025 season, posting an impressive 2.07 ERA over 69.2 innings. To top it off, he notched two saves in the postseason, further solidifying his status as one of the more appealing relievers on the market. Given his performance, Keller is well-positioned to earn a sizable payday in free agency.
Lastly, when it comes to Rogers, Soroka, Civale, and Brasier, a reunion seems unlikely, primarily because the Cubs may not have strong interest in bringing them back. Rogers, Soroka, and Civale all joined the team late in the 2025 season as short-term rentals, and it’s expected that they’ll explore opportunities elsewhere this winter.
Chicago Cubs: Expect disappointing free agent offseason with 2027 MLB lockout looming
Read More
For More Great Chicago Sports Content
Get the latest Chicago sports news, analysis, and breaking stories on the Bears, Bulls, Blackhawks, Cubs, White Sox, Sky, and more! Tap the star to add us to your favorites on Google News, so you never miss a story on your favorite Chicago teams.
Follow us on Twitter at @chicitysports23 for more great content. We appreciate you taking time to read our articles. To interact more with our community and keep up to date on the latest in Chicago sports news, JOIN OUR FREE FACEBOOK GROUP by CLICKING HERE