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Home»Cubs»Chicago Cubs: Execs say team faces uphill climb in keeping star free agent
Cubs

Chicago Cubs: Execs say team faces uphill climb in keeping star free agent

Paul MagnoBy Paul MagnoApril 16, 20254 Mins Read
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Chicago Cubs right fielder Kyle Tucker (30) bats against the Hanshin Tigers during the seventh inning at Tokyo Dome.
Chicago Cubs right fielder Kyle Tucker (30) bats against the Hanshin Tigers during the seventh inning at Tokyo Dome. Mandatory Credit: Darren Yamashita-Imagn Images
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The Chicago Cubs have a good thing going with Kyle Tucker.

The three-time all-star has been killing it this season and his presence in the middle of the Cubs lineup has made everyone around him so much better.

The only problem is that nobody quite knows how long the Cubs’ good thing will last.

Coming to Chicago in a trade with the Houston Astros for Isaac Paredes, Heyden Wesneski, and highly-regarded prospect Cam Smith, Tucker is eligible for free agency at the end of this season. So, it’s very possible that the multi-tool asset could be a one-year-and-done Cub.

Big Money Coming For Kyle Tucker

Chicago Cubs outfielder Kyle Tucker (30) hits a two-run home run against the Arizona Diamondbacks in the fifth inning at Chase Field.
Mar 29, 2025; Phoenix, Arizona, USA; Chicago Cubs outfielder Kyle Tucker (30) hits a two-run home run against the Arizona Diamondbacks in the fifth inning at Chase Field. Mandatory Credit: Rick Scuteri-Imagn Images

The 28-year-old star will demand mega-money in a long-term deal, with estimates ranging anywhere from $365 million to $475 million over ten years. Vladimir Guerrero Jr.’s recent 14-year, $500 million contract extension with the Toronto Blue Jays showcased a ballpark figure of what may be headed in Tucker’s direction.

Mark Feinsand of MLB.com recently wrote a piece, quoting several unnamed MLB execs, regarding what the buzz out in the baseball wild says about the future of the Cubs-Tucker relationship.

Spoiler Alert: The consensus belief won’t register as good news for Cubs fans.

Can The Chicago Cubs Keep Tucker?

MLB: Philadelphia Phillies at Chicago Cubs Tom Ricketts
Chicago Cubs owner Tom Ricketts is seen after a game between the Chicago Cubs and the Philadelphia Phillies at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images

“He’s likely to be the best player on the market by a decent margin; I can’t imagine him giving up the opportunity for a bidding war to potentially take place for his services,” a National League executive told Feinsand.

“We are talking about a left-handed hitter who produces similar WAR and more consistent offensive value [than Guerrero Jr.],” added an AL exec.

“If he wants to stay in Chicago, he can always sign there in the winter,” another NL exec said, pointing out that the conditions of Guerrero’s extension don’t really apply to the Cubs-Tucker dynamic. “Prior to that, I imagine it would take a massive overpay to get him to forgo an opportunity on the open market. Since he’s a couple years older than Vlad and doesn’t have the same tie-in with the Cubs that Vlad has with the Jays — or with the country, for that matter — I would be surprised if they would be willing to go far enough during the season to make him bite early.”

And if all of this hasn’t already led to the Cubs faithful losing hope in their famously frugal ownership signing Tucker, another exec would add salt to an about to be opened wound.

“An All-Time Terrible Trade”

Chicago Cubs right fielder Kyle Tucker (30) during the ninth inning against the Los Angeles Dodgers during the Tokyo Series at Tokyo Dome.
Chicago Cubs right fielder Kyle Tucker (30) during the ninth inning against the Los Angeles Dodgers during the Tokyo Series at Tokyo Dome. Mandatory Credit: Darren Yamashita-Imagn Images

“If the Cubs don’t extend him, that may go down as an all-time terrible trade,” the NL executive said.

There have been some reports that there are at least the faintest beginnings of talks between Chicago and Tucker’s team. And some insiders believe that Tom Ricketts and the Ricketts family ownership face a must-extend-Tucker public relations ultimatum headed into talks.

At the very least, where there was once no hope of getting Tucker signed up, there’s is now the faintest glimmer.

“If they’re indeed talking, that at least shows some interest on both sides,” an NL executive is quoted as saying. “The Cubs are a great place to play; I’m sure they want to keep him, which was part of the value of trading for him. I don’t see why it wouldn’t be a possibility.”

And, to close with some positivity, there was one executive who believes that the Cubs-Tucker (re)union is likely.

“He’s with a team who can do it, so I think he will,” an AL exec opined.

As the saying goes, from his lips to God’s ears.

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BY Paul Magno

Paul Magno is a trending news writer for ChiCitySports.

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