The Chicago Cubs' playoff run is over, and the focus has shifted toward the offseason. While there is some time before decisions need to be made, Jed Hoyer and company likely already have the whiteboard filled out with potential scenarios.
Of course, one of the procedural moves that will happen upon the conclusion of the World Series is players electing for free agency. Free agency will be a curious test for the Cubs this offseason, who might be operating with the potential work stoppage after the 2026 season in mind. That could be a reason why the Cubs once again don't spend to the mean that a team in baseball's third-largest market should be at.
Nonetheless, there is no shortage of 2025 Cubs who will become free agents once the World Series is over. Note that the Cubs have several players who have varying degrees of contract options for the 2026 season, and they are not included in this list. Most notably, Shota Imanaga's option is one of the key decisions of the offseason.
- Kyle Tucker, OF
Kyle Tucker is easily the biggest free agent the Cubs have this offseason. Given the awkwardness that has surrounded the Cubs and Tucker during the second half of the season, it's hard to make a case that the two sides will find common ground on a new deal. Still, expect the Cubs to attach a qualifying offer to his free agency.
- Taylor Rogers, LHP
Acquired by the Cubs at the MLB trade deadline this season, Taylor Rogers has had a forgettable run during the closing months of the season. There likely won't be much interest from the Cubs in bringing back the veteran southpaw.
- Michael Soroka, RHP
Trading for Michael Soroka may prove to be the most polarizing decision of the Cubs' season. Giving up two top-20 prospects for the right-handed starting pitcher at the deadline, a shoulder injury nearly wiped out all of Soroka's time with the Cubs. Used as a reliever to end the season, each side likely will be looking elsewhere this offseason.
- Ryan Brasier, RHP
Trading for Ryan Brasier was Jed Hoyer's band-aid approach to addressing the bullpen last offseason. Ending the season with a groin injury, it seems that Brasier's time with the Cubs is proving to be one and done.
- Caleb Thielbar, LHP
Caleb Thielbar was excellent out of the bullpen for the Cubs this season. There remains a shortage in the Cubs' system for left-handed relief pitchers, and that should push the Cubs toward trying to bring back the veteran next season.
- Brad Keller, RHP
Signing Brad Keller to a minor-league deal was one of the best moves of the offseason for the Cubs. Keller was the bullpen ace for the Cubs this season, and while there is some volatility when it comes to veteran relief pitchers, the Cubs should find a way to keep the 30-year-old.
- Drew Pomeranz, LHP
Drew Pomeranz proved to be a hidden gem in the Cubs' bullpen during the first half of the season, but the underlying metrics suggest there was some luck involved in his success. Chances are the Cubs thank Pomeranz for his efforts this season, and then let him walk once free agency starts.
- Carlos Santana, 1B
The Cubs' signing of Carlos Santana at the start of September never quite made sense, and the results suggest that the aging veteran may be close to calling it a career. Santana will not be back with the Cubs in 2026.
- Willi Castro, utility IF/OF
Willi Castro didn't exactly have the success with the Cubs that made him one of baseball's best utility players during his time with the Minnesota Twins. Castro still should have a healthy market this offseason, and the Cubs will likely be willing to give his spot on the bench to one of their top prospects.
