This Crucial Decision Will Shape The Chicago Cubs Offseason

Chicago Cubs fans won't want to be thinking about the offseason right now. This is because they're about to face the Milwaukee Brewers in a winner-take-all Game 5 of the NLDS on October 11.

If the Cubs can secure a road win after being down 2-0 in this series, they will move on to the NLCS, where they will face the defending World Series champion Los Angeles Dodgers.

And if they come up short against Milwaukee, then their 2025 season will be over, and the team and fan base will turn their attention to the offseason.

It's no secret that Kyle Tucker is going to become a free agent and will be sought after by many teams. In fact, there's a case to be made that he's the No. 1 free agent who will be available this winter, and some estimates suggest that he's going to be able to secure a deal of around $400 million.

Chicago Cubs outfielder Kyle Tucker (30) is greeted in the dugout on October 2, 2025 — David Banks-Imagn Images

The Cubs are surely going to want Tucker back, as they probably wouldn't have made it this deep into the postseason without him. However, will they be willing to pay a king's ransom to bring King Tucker back to Chicago?

Kyle Tucker Free Agency Spending Calls Mets' Toughest Free Agency Decision

These questions seem to be the basis of Bleacher Report's Zachary D. Rymer saying that "Where to draw the line on Kyle Tucker" is the biggest decision the Cubs will face this offseason in an October 11 article.

While there's a clear case to be made that Tucker is worth the $400 million or so he'll receive from some team this offseason (Spotrac projects he'll sign a 10-year, $385 million deal), that doesn't necessarily mean it's in the Cubs' best interest to give that money to him. Not only does Chicago's front office simply not offer behemoth contracts to players, but they could use a chunk of that money to improve their roster in other ways.

"These fans deserve the world." 💙

Kyle Tucker could barely hear himself think tonight at Wrigley Field! pic.twitter.com/BRYEWwDAXA
— MLB (@MLB) October 10, 2025

Plus, Tucker's average second-half of the season provides a decent excuse for Chicago to move on from him. Still, those who have watched Tucker's baseball career know that he's a major difference maker on every team he has played for, and the Cubs' offense will suffer without him in the middle of their lineup.

The decision on where to draw the line on Tucker will not only affect whether the Cubs could re-sign him, but will also have an impact on what they do for the rest of the offseason. This is why there's so much attached to what Chicago decides.

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