The Chicago Cubs have a lot on their plate.
Not only do they have a shrinking lead atop the NL Central Division to defend, whittled down to 2 game ahead of the Milwaukee Brewers as of this writing, but they also have some pressing issues concerning their immediate future.
Chief among those issues is the future of multi-tool right fielder Kyle Tucker, who is set to become a free agent at the end of this season and will demand a hefty contract as the top available position player on the market. Early estimates place the 28-year-old’s worth around $500 million, with that number likely to grow as major market heavy hitters like the New York Yankees, Los Angeles Dodgers, Boston Red Sox, and Philadelphia Phillies are rumored to be in on the bidding.
Selling Kyle Tucker on the Chicago Cubs

It’s likely that the frugal Cubs ownership would lose soundly in any such bidding war. So, Chicago’s best shot at keeping Tucker is via contract extension before the end of the season. But to do that, Tucker must be sold on the Cubs being the right place to play out the rest of his career.
Chicago is a beautiful place with a loyal fan base, but Tucker, who’s not a flashy or boisterous guy, seems to be primarily focused on winning. The first hurdle in convincing him to extend is to convince him that the organization is serious about building a championship atmosphere.
And that’s where the next month or so plays a vital role in doing that.
Proving their dedication to winning

The Cubs have the magical aura of a championship team right now, but they also have some glaring weaknesses that could bring a compelling, entertaining 2025 season into full collapse by the fall. Specifically, pitching is a concern, especially in a thinned-out starting rotation that is nothing but crossed fingers and wishful thinking beyond Shota Imanaga and Matthew Boyd.
The team urgently needs rotation help and everyone knows it. Chicago’s front office, headed by president of baseball operations Jed Hoyer, is reportedly on the case, working to make deals well before the July 31 deadline. But there’s no guarantee that the right deal(s) can be made.
An inability to pull the trigger on what everyone knows must be done to win in the here and now will reflect poorly on the entire organization’s true dedication to winning. And it may weigh heavily on Tucker’s decision as to whether he wants to stick around in Chicago for the next decade or so.
Tucker speaks

“The fanbase has been nothing but great to me, and I’ve enjoyed my time here and it’s been a blast,” Tucker recently said in an interview with NBC Chicago’s Mike Berman.
“I’ve had a phenomenal first half of the season here so far. It’s been nothing but great. I could definitely see myself in that situation [of re-signing with the Cubs], but obviously there’s some other stuff we’ve got to get through. But I mean I’ve had nothing but a phenomenal time here.”
“You definitely feel the love from the fanbase and the team, so I mean it definitely plays a part in [any decision],” he added. “I don’t know where the future’s going to be or what not, but for now I’m here and I’m really enjoying it.”
That “some other stuff” is the ominous part of Tucker’s positive report on Chicago. Money is part of that “other stuff,” of course. The other part is the organization, itself, and whether they are truly serious about building a winner over the long haul.
He’ll get the answer to that within the next month or so.
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