The baseball world was shocked by a long list of names on the Chicago Cubs roster heading into free agency shortly after the 2025 MLB season closed. According to a report from Bleacher Nation on October 29, the Cubs will see at least 10 players leave immediately, with several more expected to leave in the coming days.
“For that reason, I figured it was a good time to remind folks of the many, many free agents the Cubs have hopping off the roster very soon.”
A slew of names like Ryan Brasier, Willi Castro, Brad Keller, Taylor Rogers, Carlos Santana, and Kyle Tucker have been listed as “Immediate Free Agents” — meaning they will leave the team immediately after the season ends.
It’s not just a few small changes: this period has been described as a sudden and violent personnel shakeup. The Cubs aren’t just losing players — they’re losing “stabilizing resources.” The departures include pitchers, hitters, and catchers — a diversity that spreads the hurt across the team.
The team is also facing a difficult choice: in addition to the “immediate departures,” there is also a group of “potential departures” as the team must decide on contract options like Shōta Imanaga, Andrew Kittredge, and Colin Rea.
This raises a series of thorny questions:
How will the Cubs reshape their roster while losing so many key players?
Can the team retain the “reckless voodoo” identity that fans love, or will it fall into a prolonged slump?
What part of the budget is being shifted — and what part is a signal that the Cubs are entering a full-scale rebuild?
One thing worth noting: the team has only four arbitration-eligible players — and the likelihood that at least one of them (Reese McGuire) will not be renewed could increase the list of departures to 12 or more.
Cubs fans are used to change — but they’ve never seen such a complete shakeup. The joyous moments of victory and playoff night are now being replaced by a rebuild. And with financial stability and strategy on the line, the conversation is not just about who’s leaving, but who’s staying and who’s rebuilding.
If the Cubs don’t find replacements quickly — or have a clear strategy to win back the fans — the 2026 season could be the start of a long, dry spell. Instead of playoff cheers and fireworks, team meetings with new faces and new hopes will become a familiar sight.
And Chicago fans, accustomed to “Fly the W,” may have to wait longer — a lot longer — for this night of crisis to end and for the lights to return. The Cubs are at a crossroads: rebuild or lose faith.
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