October 13, 2025 | CHICAGO
The Chicago Cubs are heading into one of the most dramatic offseasons in franchise history. After a crushing Game 5 loss to the Milwaukee Brewers in the NLDS, reports suggest the Cubs front office is preparing for sweeping roster changes that could reshape the team from top to bottom.
“We know there’s going to be change, but we’re focused on building something that lasts,” manager Craig Counsell said. “We’ve got a lot of decisions to make, but we’re confident in the direction we’re heading.”
Here’s a full breakdown of who’s staying, who’s gone, and what comes next in the Cubs’ offseason drama.
Who’s Likely Staying: Core Players Safe for 2026
Shota Imanaga (LHP)
Despite postseason struggles, the Japanese left-hander remains a valuable long-term asset. With three years left at $19 million per season, the Cubs are expected to retain Imanaga as part of the starting rotation’s foundation.
Colin Rea (RHP)
Rea has been a low-cost success story, making just $6 million and delivering consistency in the back end of the rotation. Chicago plans to exercise his contract and keep him for depth and stability.
Who’s Gone: Key Cubs Set for Devastating Departures
Kyle Tucker (OF)
Perhaps the biggest loss of the offseason, All-Star outfielder Kyle Tucker is expected to walk in free agency. The Cubs simply can’t outbid powerhouses like the Yankees, Dodgers, or Red Sox for his projected $300–$500 million deal. His departure will leave a massive void in Chicago’s lineup and outfield.
Brad Keller, Drew Pomeranz, Caleb Thielbar (Relievers)
All three were crucial in solidifying the bullpen, but the Cubs’ front office has historically avoided spending big on relievers. Expect all three to hit free agency, with Keller being the only one who might return thanks to Counsell’s backing.
Justin Turner (1B/DH)
At 41 years old, Turner’s leadership was valuable — but his defense and declining bat make him expendable. The Cubs will likely decline his $10 million mutual option and pay the $2 million buyout instead.
Aaron Civale (RHP)
A solid swing-man but too expensive to keep. With multiple teams willing to offer more, Civale is expected to leave in free agency.
The Last Straw: Players Certain to Leave Chicago
Andrew Kittredge (RHP)
The Cubs won’t pick up his $9 million club option. Unless he takes a steep pay cut, Kittredge will move on.
Willi Castro (IF/OF)
Castro’s versatility has value, but market competition makes his return unlikely. Expect the Cubs to lose him to a higher bidder this winter.
Carlos Santana (1B)
At 40, Santana’s time in Chicago appears over. With Michael Busch establishing himself at first base, Santana is no longer needed and will not be re-signed.
Taylor Rogers & Ryan Brasier (Relievers)
Both failed to show consistency out of the bullpen. The front office is expected to cut ties with both pitchers to open space for younger arms.
What’s Next: Cubs Face Franchise-Defining Offseason
With half the roster in flux, the Cubs are entering a pivotal offseason filled with difficult choices. Will they double down on Counsell’s long-term vision, or shift toward a faster rebuild?
Jed Hoyer and the front office are expected to explore trade opportunities, mid-tier free agents, and possibly a new offensive centerpiece to replace Tucker.
One thing is certain: this will be one of the most unpredictable and high-stakes offseasons in recent Cubs history.
Stay tuned for more Chicago Cubs offseason rumors, trade news, and free agency updates as the front office begins reshaping the roster for 2026.
