CHICAGO, ILLINOIS – OCTOBER 8: Kyle Tucker #30 of the Chicago Cubs takes the field during player introductions prior to game three of the National League Division Series against the Milwaukee Brewers at Wrigley Field on October 8, 2025 in Chicago, Illinois. (Photo by Brandon Sloter/Chicago Cubs/Getty Images)

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Jackson Roberts

By Jackson Roberts

Contributing Sports Writer

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The Chicago Cubs seemingly knew what they signed up for.

Last December, the Cubs traded for three-time (now four-time) All-Star right fielder Kyle Tucker with only one year to go on his rookie contract. It was clear then that Tucker would be the biggest prize of the upcoming free agent class, and it's just as clear now, even after a somewhat choppy second half of the regular season.

Negotiations for a potential extension are tough to open up when a player with Tucker's track record is less than a year from free agency, and throughout the year, it was never reported that Tucker and the Cubs got anywhere close to such an extension. But now that all 30 teams can sign him, what are Chicago's chances of getting him back?

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CHICAGO, ILLINOIS - OCTOBER 8: Kyle Tucker #30 of the Chicago Cubs takes the field during player introductions prior to game three of the National League Division Series against the Milwaukee Brewers at Wrigley Field on October 8, 2025 in Chicago, Illinois. (Photo by Brandon Sloter/Chicago Cubs/Getty Images)

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MLB.com Cubs insider Jordan Bastian had a fairly pessimistic take on the situation in a Saturday column.

"The Cubs knew it might very well be a one-year arrangement when they swung the blockbuster trade with the (Houston) Astros in December to add Tucker to the lineup," Bastian wrote. "Tucker is 28 years old, ranks 11th in MLB in bWAR (25.4) over the past five seasons and is arguably the best all-around hitter on the free-agent market this winter.

"The odds seem to point toward Tucker signing elsewhere, but the Cubs would certainly have an edge on the recruiting side of things. He just spent a season with the ballclub, getting familiar with the organization, teammates, staff, facilities and city. There is nothing to sell Tucker on from that perspective."

The albatross, which Bastian hints at in his summary above, is the money involved. Tucker is projected for a 10-year, $401 million contract by Spotrac. That projection, assuming it's somewhat accurate, is more than double the largest contract the Cubs have ever handed out, either via free agency or extension (Jason Heyward, $184 million).

Plus, if the Cubs are deep enough at any position to handle the loss of a star, it's the outfield, with Pete Crow-Armstrong, Ian Happ, Seiya Suzuki, and rookie Owen Caissie all under contract for next season.

At this point, the breeze certainly seems to be blowing toward Tucker leaving the Windy City this winter.

More MLB: Astros Sign Former 1st-Round Pick to Rare Free-Agent Contract

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