Insider Hints That Cubs Could Reunite With ‘Old Friend' In Free Agency

The options for the Chicago Cubs to improve their roster in free agency this winter are dwindling.

Cubs fans expected Jed Hoyer and the rest of Chicago's front office to be active on the free agency market this offseason, especially after the team conveyed that they intended to make use of their budget. However, the team has yet to make a splash and has reportedly bowed out regarding their interest in several players because they ended up being too costly.

But what's perhaps most interesting is which players the Cubs are showing the most interest in. There's a strong case to be made that Chicago needs to bolster their pitching staff more than their position players, but reports indicate that the Cubs are eyeing position players more than pitchers at this point.

It's clear that Chicago is among a few finalists to sign Alex Bregman, and reports surfaced on January 4 that the Cubs' brass is also keeping close tabs on Bo Bichette's market. While those players would be great additions, most fans would probably prefer to bring Cody Bellinger back to Wrigley Field.

New York Yankees right fielder Cody Bellinger (35) prior to a May 26, 2025 game — New York Yankees right fielder Cody Bellinger (35) prior to the game against the Los Angeles Angels at Angel Stadium. | Jayne Kamin-Oncea-Imagn Images

Bellinger hit .272 with an .814 OPS, 29 home runs. 98 RBIs and 13 stolen bases in his 2025 season with the Yankees after spending the 2024 campaign in Chicago. And even though there isn't a clear fit for him in the field, Bellinger is the type of talent that a club will move players around to make room for.

Cubs Could Reunite With ‘Old Friend’ Cody Bellinger, Insider Says

It appears that the Cubs are doing so, as New York Post MLB insider Jon Heyman made an X post on January 4 that read, "Cubs checked in on old friend Cody Bellinger. They’re also known to be in touch with Bregman, Bichette and other top players. The incumbent Yankees remain in talks with Bellinger, their stated No. 1 priority. Mets, Dodgers, Giants are among others showing interest in Bellinger."

Cubs checked in on old friend Cody Bellinger. They’re also known to be in touch with Bregman, Bichette and other top players. The incumbent Yankees remain in talks with Bellinger, their stated No. 1 priority. Mets, Dodgers, Giants are among others showing interest in Bellinger.
— Jon Heyman (@JonHeyman) January 4, 2026

There were rumblings that the Cubs and Bellinger were in communication earlier this offseason, but things had gone quiet over the past few weeks.

While it will be nice for fans to see that Chicago is still a suitor for the 2019 NL MVP, the expectation is that he will either re-sign with the Yankees or head to the Mets this winter, thus making a reunion with the Cubs a long shot.

But that doesn't mean it's impossible, especially if the Cubs come with a correct offer.

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