The Chicago Cubs have done a great job when it comes to identifying and developing young talent.
While it’s exciting for any fanbase to see star prospects emerge and young players become the next key part of the roster, where Cubs fans have criticized the organization is for their inability to combine that philosophy with spending on elite free agent talent.
Chicago is one of the biggest markets in Major League Baseball, yet this franchise does not act like that, continually toeing the line between paying the luxury tax and staying under that payroll total. This has prevented them from adding superstar-caliber players, something which has held them back from being true World Series contenders.
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During the upcoming offseason, the ownership group has an opportunity to change that reality, with Kyle Tucker set to hit the open market and the Cubs being the leaders in the clubhouse when it comes to their chances to re-sign him based on the familiarity between the two sides because he is playing for them this year.
Yet, it’s unclear if Chicago is going to do what it takes to keep the elite right fielder in their midst based on their history of being cheap when it comes to handing out lucrative deals.
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Prominent MLB insider Jeff Passan of ESPN believes that could continue this winter, with him having a hard time believing the Cubs are going to offer Tucker a contract that will ensure he doesn’t leave the confines of Wrigley Field.
“I think the Cubs are going to have a limit that they’re not going to want to go past. The reason I have pause on saying unequivocally ‘yes they are the favorite’ is because I’ve seen this time and again,” he said during an appearance on the “Cubs Weekly Podcast.”
It’s hard to argue with what Passan said based on how Chicago has operated in the past, continually coming up short in bidding wars for free agents and not trading for expensive players when the opportunity presents itself.
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.@JeffPassan believes the Cubs are the favorites to land Kyle Tucker, but “have a limit they’re not going to want to go past.”
He joins @LanceBroz on the Cubs Weekly Podcast 🎧
— Marquee Sports Network (@WatchMarquee) August 28, 2025
Even with the struggles Tucker had for the latter stages of the summer when he was dealing with an injury, it is clear how much of an impact the slugger has had on this team, giving them a real contact and power threat in the lineup while providing high-end defense in the outfield.
Not being aggressive to bring him back would be another frustrating blow to this fanbase, especially after the Cubs traded away a haul — including future star Cam Smith and 2025 All-Star Isaac Paredes — to bring Tucker to town in the first place.
Passan believes Chicago should still be considered the favorites to keep Tucker beyond this year, but he also thinks there is already a price point in place where the organization won’t go past, limiting themselves once again when it comes to landing a notable free agent.
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