The Chicago Cubs are facing a major decision on Kyle Tucker as the postseason unfolds. The star outfielder, who came over from Houston before the 2025 season with just one year left on his deal, is set to hit free agency once Chicago’s playoff run ends.
Right now, the Cubs are battling Milwaukee in the NLDS while the Astros are already looking ahead to 2026 after missing the playoffs. That’s a role reversal from recent years, when Houston was the perennial contender and Tucker was a key piece of their championship runs.
The question everyone’s asking: will Chicago pay up to keep him?
Erik Beaston of Bleacher Report doesn’t think so. He’s predicting Tucker moves on this winter, with the Philadelphia Phillies emerging as an intriguing landing spot alongside other big-name free agents like Pete Alonso and Kyle Schwarber.
“Tucker was one of the stars of the Astros teams that routinely competed for the World Series title. He is a championship piece who can contribute to any contending team, including Chicago, and make them better.”
But here’s the thing – championship pieces don’t come cheap. Beaston thinks it’ll ultimately come down to whether the Cubs are willing to match whatever the market offers for a player of Tucker’s caliber.
His prediction: Tucker moves on, with the Phillies as an intriguing option.
That would be a massive addition for Philadelphia. Tucker’s still just 28 years old and coming off a solid season in Chicago – .266/.377 with 22 homers, 73 RBIs, and 25 stolen bases across 136 games. Those aren’t eye-popping numbers by his standards, but they show a complete player who can impact games in multiple ways.
The timing works for Philadelphia too. They’re clearly in win-now mode and have shown they’re not afraid to spend on the right players. Adding Tucker’s speed and power to that lineup would give them another dynamic piece alongside their established core.
What makes this situation interesting is how much the landscape has shifted. Houston traded Tucker partly because they couldn’t afford to lose him for nothing, but now they’re on the outside looking in while Chicago is making playoff noise. Still, it’s hard to imagine the Cubs letting a player of Tucker’s caliber walk without a fight.
The market will ultimately decide Tucker’s fate. If he’s looking at a deal in the $150-200 million range – which seems realistic for a player entering his prime years – that’s a significant commitment for any organization.
Whether that’s Chicago, Philadelphia, or someone else entirely, Tucker’s next contract should be one of the more fascinating storylines of what’s shaping up to be a busy winter.
