The Chicago Cubs seemingly went all in to win this year, and it’s paid off for the most part. Chicago, after swinging a massive trade for Kyle Tucker, turned its attention to the World Series.

The Cubs may not finish the year at the top of the National League Central, but they’re headed to the postseason. With the Cubs in the postseason, anything can happen. They’re not the NL favorites to win the World Series, but with the talent on their roster, it doesn’t matter what the projections say.

Either way, this offseason is going to be crucial for their future. Which three free agents could the Cubs target in order to bolster the roster for 2026?

The Cubs could look to steal veteran pitcher Nick Martinez from the Cincinnati Reds.

Martinez works as a starter and a reliever for the Reds. He does a solid job in both roles, and the Cubs could look to sign him to a one- or two-year deal with that kind of workload in mind.

Chicago could have used more pitching all year, so having a flexible arm like Martinez would have worked to its benefit. With the veteran on the market, the fit makes sense this winter.

RHP Ryan Helsley

Aug 25, 2025; New York City, New York, USA; New York Mets pitcher Ryan Helsley (56) delivers a pitch against the Philadelphia Phillies during the eighth inning at Citi Field. Mandatory Credit: Gregory Fisher-Imagn Images / Gregory Fisher-Imagn Images

The Cubs could also look to add a closer in free agency, which might lead them to New York Mets righty Ryan Helsley.

Helsley was dominant in the first half, but fell off when he joined the Mets. His price tag is likely a bit lower now than it was a few months ago, though his talent is still there. The Cubs could target him on a four-year deal to make the flamethrower the closer of the future in the Windy City.

The top name for the Cubs this winter is Tucker.

Chicago likely wouldn’t have traded for the slugger if it didn’t believe it could re-sign him. This is going to be an uphill battle, as Tucker is projected to sign for between $400 million and $500 million on the open market. The Cubs have never given out a deal like this, but it would be the perfect time to do so.

Signing Tucker to a deal for eight or 10 years would alter the future of the franchise in Chicago.

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