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Insider Believes Cubs Can Re-Sign Free Agent Superstar if They Make Right Offer

Originally posted on Chicago Cubs on SI
By Michael Brauner | Last updated May 16, 2025 12:00 PM ET

The Chicago Cubs have experienced a resurgence this season, and at the center of it has been their newest superstar.

Chicago has the best offense in baseball, and a ton of it has been powered Kyle Tucker after the Cubs made a massive trade for him this offseason.

Tucker is putting up legitimate MVP-like numbers through the first quarter of the season, which is of course good news for Chicago.

It's a double-edged sword however as Tucker is a free agent next winter and the better he plays, the more difficult it's going to be to keep him.

The general belief however is that the Cubs will have a leg up over every team who wants him due to the possibility that a special season with an iconic franchise in a classic ballpark will make him want to stay.

Could the Cubs Sign Tucker to an Extension Before He Hits Free Agency?

Prominent MLB insider Jon Heyman spoke about this reality during a recent appearance on MLB Network, saying if Chicago is willing to pony up, they can keep Tucker in the fold for the next decade-plus.

"This is a guy I think will consider them if they make him the right offer..."

- @JonHeyman on a potential Kyle Tucker-Cubs contract extension pic.twitter.com/xZHKcNbB6T
— MLB Network (@MLBNetwork) May 14, 2025

"I talked to him this weekend and he didn't want to discuss potential talks, but he did say he's really enjoying his time as a Cub," Heyman said of Tucker. "I do think he will listen, I do think the expectation is they will come to him this summer and try to figure it out....This is a guy I think will consider it if they make him the right offer."

Heyman did go on to talk about the fact that just because Tucker seems to love playing in the Windy City, that does not mean it's going to be easy to retain him.

It is extremely notable though that he believes Tucker would be willing to sign a deal before hitting free agency if the number was right.

Tucker has slashed .263/.371/.526 this season and is one of just three players in baseball to have stolen ten bases and hit three home runs.

He is among the most valuable stars in the sport and his eventual contract -- whether it's with the Cubs or somewhere else -- is going to reflect that.

Chicago seems to have a real chance here to lock up the face of their franchise for the remaining productive years of his career if they are willing to pay him.

That deal gets a lot easier to sign if Tucker is willing to entertain an extension before hitting the open market.

This article first appeared on Chicago Cubs on SI and was syndicated with permission.

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