The Chicago Cubs are a team that everyone will be keeping an eye on this offseason, following the free agency saga of right fielder Kyle Tucker.

Will the Cubs be able to retain him this offseason? Early indications are that this will be a one-and-done relationship and that he will depart on the open market. That would be a huge blow to Chicago, given how much was surrendered to acquire him in the first place. He has also been a major part of the team’s success this year; they go as he does.

Losing a player of that caliber for nothing in free agency would certainly hurt. But at least the Cubs can rest a little easier knowing they have players capable of stepping into the lineup. They don’t have the star power Tucker does, at least not yet, but Owen Caissie and Kevin Alcantara possess immense upside as two of the team’s top prospects.

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Alas, should Tucker depart, it is expected that the Chicago front office would go hunting for some star power to offset the loss. One intriguing option would be Baltimore Orioles catcher Adley Rutschman.

Widely expected to be made available this winter, the Cubs were recently named one of the top landing spots for him in a trade.

What could a deal between the two sides look like? Zachary D. Rymer of Bleacher Report put together a hypothetical trade with the teams with Rutschman heading to Chicago in exchange for right-handed pitcher Javier Assad and right-handed pitching prospect Jaxon Wiggins.

If that is all it would take to acquire the two-time All-Star, the Cubs would jump at that deal. Catcher doesn’t look to be a pressing need with Carson Kelly and Miguel Amaya combining to be an excellent duo in 2025. But Kelly’s production has flatlined since a hot start with a .661 OPS since May 27. Amaya has had to battle injuries, and if the franchise was confident in his abilities to handle a starting role, they wouldn’t have signed Kelly in the first place.

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Even with his struggles, that date back to midseason in 2024, Rutschman’s numbers are comparable, if not better, than Kelly and Amaya. The upside he has shown is also a major upgrade. A change of scenery and some better health luck could all the the former No. 1 overall pick needs.

Cubs Dip Into Pitching Depth in Hypothetical Trade

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In terms of the trade package, this would be a worthwhile investment for Chicago to make. Assad has produced when he has been able to stay on the mound. But, good health has been difficult to come by. In 2025, he has thrown only 14 major league innings.

Wiggins possesses some upside while still pitching in Double-A. The Cubs showed a hesitancy to part with any top prospects ahead of the MLB trade deadline this year, but that could change once the offseason rolls around. Parting with a pitcher that has the upside of Wiggins would be tough, especially given their own starting pitching problems. But there should be money to spend on a frontend starter, especially if Tucker doesn’t return.

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