Inside The Cubs

Unexpected Yankees Star Seen As Cubs Top Free Agency Target — Why It Makes Sense

Could the Chicago Cubs sign this surging Yankees slugger in free agency?
Grant Young|
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When the New York Yankees lost superstar slugger Juan Soto to their cross-town rival Mets in free agency last offseason (which came in the form of a 15-year, $765 million deal, which is the largest contract in sports history), it was clear the Yankees needed to find someone to replace Soto's presence in their lineup.

And the Yankees accomplished this by acquiring Cody Bellinger from the Chicago Cubs, which the Cubs did in order to make space for Kyle Tucker (who they had traded for days before) in the outfield.

Bellinger went on to have a successful 2025 season. However, given Bellinger's impressive pedigree, everybody expected he would shine during his first season in the Bronx. What fans didn't expect was the season that his Yankees teammate Trent Grisham had.

New York Yankees center fielder Trent Grisham (12) celebrates on August 29, 2025
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Grisham produced an .812 OPS and 34 home runs in 2025, both of which were career-highs for the seven-year MLB veteran. And this success could not have come at a better time for the 28-year-old, given that he's set to become an unrestricted free agent this offseason.

MORE: The Good, Bad and Ugly of the Chicago Cubs’ 2025 Season

Cubs Seen As Top Trent Grisham Destination, And Why It Makes Sense

Given that the Cubs aren't likely to give Kyle Tucker the $400 million or so contract he's expected to receive this offseason, they'll need to pivot and find another outfielder to hopefully replace his production.

Grisham makes a ton of sense in this regard, which is a big reason why Bleacher Report's Kerry Miller called the Cubs one of Grisham's top potential free agency destinations in an October 14 article.

It's worth noting that the Cubs don't need any help in center field, as Pete Crow-Armstrong mans that position and isn't going anywhere anytime soon. Therefore, if Grisham (who has only played center field since 2019) isn't willing to move to another outfield spot, then he won't be signing with Chicago. But if Grisham is open to a position change, then the Cubs make perfect sense.

Spotrac projects that Grisham will sign a four-year, $49 million deal this offseason, which should be within the Cubs' budget. And because he saw similar success as Tucker during the 2025 campaign, if he can replicate that same success at Wrigley Field, then Chicago will have found a Tucker replacement at a fraction of the price.

There's a world where Grisham makes the change from one pinstripe home jersey to another this offseason and is in the Cubs' starting lineup come Opening Day 2026.

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Grant Young
GRANT YOUNG

Grant Young is a Staff Writer for On SI’s Chicago Cubs, New York Mets, Boxing, Indiana Fever, and Women’s Fastbreak sites. Before joining SI in 2024, he wrote for various boxing and sports verticals such as FanBuzz and NY Fights. Young has a bachelor’s degree in marketing and a master’s degree in creative writing with an emphasis on sports nonfiction from the University of San Francisco, where he played five seasons of Division 1 baseball. He fought Muay Thai professionally in Thailand in 2023, loves a good essay, and is driven crazy trying to handle a pitpull puppy named Aura. Young lives in San Diego and was raised in the San Francisco Bay Area.

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