Chicago Cubs will re-sign two free agent stars, let everyone else walk, analyst says

The Chicago Cubs were favored to win the NL Central Division this season and there was plenty of reason to think that would happen.

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They had added three-time All-Star third baseman Alex Bregman via free agency. They traded for emerging powerhouse starter Edward Cabrera. They even rebuilt their bullpen, signing four veteran free agent relievers. They were also poised to get a full season from 24-year-old rotation phenom Cade Horton and benefit from the return of rehabbed ace Justin Steele.

Things, of course, didn’t go entirely as planned. Actually, of the above list of expected positives, only Bregman worked out.

As things currently stand, the Cubs are in a dogfight with the Philadelphia Phillies for the top NL Wild Card seed and are also fending off the advances of the San Diego Padres and Arizona Diamondbacks in the Wild Card race.

Half the roster, gone?

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Then, no matter what happens the rest of this season, they’ll have some major roster decisions to make as a good chunk of the team will be eligible for free agency. Of the current active roster, more than half of the team could be gone by the start of the 2027 season.

Of those possible losses, there are several key veteran components—such as Ian Happ, Seiya Suzuki, Carson Kelly, Matthew Boyd, Shota Imanaga, and Kevin Gausman, among others—that could be leaving.

Fielding a winning team will be tough with so many roster spots to fill, so it’s expected that the Chicago front office will try to re-sign at least a few of their potentially outbound assets.

Who will they keep?

Joel Reuter of Bleacher Report is predicting that the Cubs will hold on to at least two of their stars—right fielder Seiya Suzuki and catcher Carson Kelly.

Per Reuter:

“The Cubs have some decisions to make with Seiya Suzuki and Ian Happ both ticketed for free agency, along with catcher Carson Kelly’s mutual option. The safe bet right now is that they will retain one, but not both, of those outfielders, while also working out a new two-year pact to keep Kelly around.”

Finding two new every day corner outfielders on a team deep into “win now” mode would be tough. So, it’s widely expected that the Cubs will move to re-sign either Suzuki or Happ. But given that Suzuki is just far superior offensively—and that he’s become a spark plug for the team’s offense—the choice between the two outfielders should be fairly straightforward.

At catcher, the team is also facing the reality that they may not have a full-time replacement for Kelly at the moment. Miguel Amaya has shown himself to be capable and prospect Owen Ayers may be the next big thing in Cubs catching, but neither is an every day replacement for Kelly at this point.

The pitching decisions made by the front office will be even more interesting. There’s actually a case to be made for letting every free agent pitcher walk. After all, the team IS at the bottom of the barrel when it comes to pitching as a unit.

Clay Holmes would be the one guy the Cubs should try to lock in. The veteran has a $12 million player option for 2027, but is not expected to exercise it. He could command as much as $70-$93 million over 3 or 4 years—and that will be a significant risk taken on a 33-year-old. But Holmes’ groundball generation plays perfectly with the Cubs elite infield defense and offers a high possibility of success through his contract.

Targeting only Holmes would mean lots of new pitchers on the roster next season and, given the staff’s problems this year, that’s not a bad thing.

Whatever the case, interesting times are ahead.

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