With a playoff run achieved, the Cubs face a pivotal offseason. Core players' contracts expire, forcing front office decisions to secure a championship window.
The Cubs' win-now window is here.
The franchise took significant strides forward during the 2025 season. The Cubs won their most games in a season (92) since 2018 and won a playoff series for the first time since the 2017 season.
Given that the Cubs are really only a few pieces away, this is go time for the front office to make multiple big moves this offseason. This might be the last time this set of core players will be together.
That’s because the Cubs roster could look a whole lot different after the 2026 campaign. Notable players like Ian Happ, Seiya Suzuki, Jameson Taillon, Matthew Boyd, Carson Kelly, and Nico Hoerner are all set to become free agents following next season.
Realistically, the Cubs are not going to be able to retain all six of those players. The front office will likely have to choose between Ian Happ or Seiya Suzuki. It’s hard to imagine Chicago signing both players next offseason, especially with Owen Caissie waiting in the wings.
The Cubs absolutely view Caissie very highly. They believe he could turn into an All-Star at some point in his career. So, Jed Hoyer probably won’t pay both Happ and Suzuki.
While it would be shocking to see Hoerner leave, getting Taillon and Boyd to both return might be a long shot. Taillon will be 35 years old at that point, and Boyd will be almost 36 years old. The Cubs might not want to pay two aging veterans.
As a result, the time is now for the Cubs to go all in on a potential World Series title. Chicago might only lose Kyle Tucker to free agency this offseason, but the front office is more than capable of replacing him with someone like Kyle Schwarber.
The same goes for Shota Imanaga if the team decides to decline his three-year, $57 million club option. The front office can easily replace him with a star pitcher like Dylan Cease, Ranger Suarez, or Framber Valdez.
Outside of those two players, the rest of the team mostly stays the same. But that isn’t the case after the 2026 season, with plenty of big-name players set to hit free agency.
That should be enough reason for the Cubs’ front office to make the necessary moves to get them over the top. They might not get another shot to win it all with players like Happ, Suzuki, and Hoerner all on the same team.