As the Chicago Cubs turn the page to the offseason and try to figure out how to take the next step as a franchise following their deepest playoff run since 2017, some real decisions are going to have to be made.

Much of the focus this winter is likely going to be on pitching, especially in the starting rotation. With that being said, a looming probable departure from Kyle Tucker is going to leave a gap in both the outfield and the lineup as Chicago tries to replace his production.

Though the second half of the season saw injuries and inconsistency from Tucker — likely related to one another — the production he had over the first few months is not simply attainable by a cheap option, or maybe not even a prospect, at least not right away.

Because of this, many Cubs fans have wanted the team to replace Tucker with another Kyle via a reunion with Philadelphia Phillies superstar Kyle Schwarber, bringing back one of their all-time favorites who is coming off the best season of his career.

While Schwarber has been connected to Chicago by some, a reunion does not feel likely purely from a roster or financial standpoint.

Sep 13, 2025; Chicago, Illinois, USA; Executive Chairman of the Chicago Cubs Tom Ricketts is seen prior to a game against the Tampa Bay Rays at Wrigley Field. / Patrick Gorski-Imagn Images

For better or for worse, paying a designated hitter the likely four-year contract for potentially up to $30 million annually that Schwarber is going to get is simply not in Chicago’s playbook. Trading for Tucker was an aggressive move, but as many predicted, they likely are not going to make a real attempt to keep him beyond the one season.

If the Cubs are going to spend some cash this winter, it likely will — and frankly should — be on the pitching staff as they try to build a championship rotation. The far bigger reasons why Schwarber coming back to Chicago doesn’t make sense though is what the organization already has in the building.

Signing Schwarber Would Block Moises Ballesteros, Owen Caissie

Charles LeClaire-Imagn Images

Ballesteros would be by far the biggest loser here if the Cubs were to make a move on Schwarber. Already a weak defensive catcher, the young slugger is likely blocked there already by Carson Kelly and blocked at first base by Michael Busch, meaning his role to playing time in 2026 may be dependent on DH being open.

The same goes for Owen Caissie, because if Schwarber occupied DH, then Seiya Suzuki likely takes over Tucker’s spot in right field and makes it tough for the top prospect in the organization to get on the field. Chicago has one of the best farm systems in baseball, and it feels like they’re getting ready to deploy it.

After Ballesteros slashed .298/.394/.474 in his 20 game sample size following a dominant stint in Triple-A not to mention Caissie’s .286/.386/.551 slash line in Triple-A this year, the kids are ready to go.

Signing Schwarber would run counter to the way the Cubs have been built, and because of that, it does not feel like the right fit for as popular a move as it would be.

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