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The Chicago Cubs have already secured a path to saying 'we tried' when it comes to Kyle Tucker's free agency this offseason. ESPN insider Jeff Passan was a recent guest on the Marquee Sports Network and all but set the stage for the Cubs to predictably come up short in the sweepstakes for Tucker this winter.
.@JeffPassan believes the Cubs are the favorites to land Kyle Tucker, but "have a limit they're not going to want to go past."
— Marquee Sports Network (@WatchMarquee) August 28, 2025
He joins @LanceBroz on the Cubs Weekly Podcast 🎧
As long as Jed Hoyer remains the President of Baseball Operations for the Cubs, there is always going to be a line in the sand with any move that they make. Hoyer is extremely stubborn when it comes to his baseball decisions, and for a free agent, if an offer extends beyond his comfort zone, the result is Hoyer and the Cubs backing away from the deal.
Along those lines, we shouldn't glance over Passan's reference to the Cubs' pursuit of Alex Bregman last offseason. Every message the Cubs were leaking suggested that the front office was aware of the fact that Bregman could be the difference maker between the Cubs being just good enough this season and being great. The Cubs' offer, however, didn't match that urgency as they didn't offer Bregman the most money, didn't offer Bregman the most years, and didn't offer Bregman the highest AAV.
Jeff Passan sparks Cubs fans’ worst fear about offseason plans
Given the precedent that the Cubs have set, it's hard to imagine they move off that approach for Tucker. Considering that Tucker's sweepstakes almost certainly will include the Los Angeles Dodgers, New York Yankees, Boston Red Sox, and Philadelphia Phillies, it feels inevitable that the bidding will move past the Cubs' reach almost instantly.
That speaks to a larger problem surrounding the Cubs' front office. The stage is set for the team's contention window to fully burst open, and they have the money to ensure it is propped open beyond just the 2026 season. Instead, the Cubs have been afraid to spend money that goes against their misguided mantra of "intelligent spending". Throw in the idea that the Cubs are also afraid of the potential work stoppage in 2027, and it's hard to have any optimism for the team's chances of bringing back Tucker.