Cubs 'unlikely' to keep projected $525M All-Star in free agency, per MLB insider

Are the Chicago Cubs really a big-market team? Because they don't often act like one.

The Cubs are Major League Baseball's fourth most valuable team, per Forbes, at $4.6 billion. But they only fielded the 10th-largest Opening Day payroll in 2025, behind teams in smaller markets like the Houston Astros and the San Diego Padres.

Now, the Cubs have superstar Kyle Tucker on a one-year contract. They traded those Astros three quality players to get their hands on him. And at age 28, he's the perfect candidate for a long-term extension.

Should we expect that extension? One baseball insider says not to hold our collective breath.

On Tuesday, while highlighting the importance of the upcoming trade deadline for the Cubs, Ken Rosenthal of The Athletic emphasized that he believes it is unlikely Chicago owner Tom Ricketts will green-light the kind of contract required to keep Tucker in town.

"The Cubs could lose five more important players to the open market after 2026, making an aggressive push at this year’s trade deadline all the more imperative," Rosenthal wrote. "And while the Cubs might retain some of those players, they are unlikely to keep all of them, Tucker in particular.

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"The Cubs actually are positioned perfectly to sign Tucker. Their only player under contract beyond 2026 is shortstop Dansby Swanson, who is signed through ’29. Of course, the reason their commitments are so low is because Ricketts seems resistant to the notion of paying a player in his decline years. Which, with Tucker, he almost certainly would need to do."

Tucker is projected for a 12-year, $525 million contract by Spotrac. It's worth noting that the biggest contracts the Cubs have ever handed out were $184 million to Jason Heyward and $177 million to Dansby Swanson. 

Counting on the Cubs to triple their franchise record contract seems like a bit of a stretch indeed, even if their profit margin suggests they can afford it. Seeing Tucker in another uniform so soon would be a gut punch to Cubs fans, but there's not much they can do to force ownership to write the check.

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