Cubs May Lose Key Free Agent Reliever To Yankees This Offseason

The Chicago Cubs head into the offseason with the goal of improving their pitching staff both in the bullpen and in the starting rotation, whether it be via free agency or the trade market.

For president of baseball operations Jed Hoyer, that work has already started. The Cubs retained Shota Imanaga on the qualifying offer and has been linked to other starters on the market while bringing in Phil Maton for the bullpen.

Often though, while new additions are exciting, retaining talent can be the best way to have continued success, and Chicago is left with a question in that department as star reliever Brad Keller joins the open market.

According to a report this week from Joel Sherman of the New York Post (subscription required), the New York Yankees are one of the teams interested in Keller, and they could take advantage of both strengths out of the bullpen and starting rotation.

Yankees Reportedly Interested in Signing Cubs Star Brad Keller

Brad Keller of Chicago Cubs walks off field — Chicago Cubs pitcher Brad Keller (40) looks on during a game against the Chicago White Sox at Rate Field. | Patrick Gorski-Imagn Images

Interestingly, much of the reporting surrounding Keller and his market is that he's garnering interest both as a reliever and a starting pitcher, where he began his career. He excelled out of the bullpen in 2025 for Chicago to the tune of a 2.07 ERA, 0.962 WHIP and 1.4 bWAR with the highest strikeout rate of his career.

Before making the full-time switch, though, Keller began his career as a starter, and with the resurgent season for the 30-year-old, it seems opposing teams believe he could switch back. In terms of the Yankees specifically, it sounds like it could be a bit of both should he wind up in the Bronx.

Sherman's report indicated New York has more interest in Keller as a reliever, but that due to their various injuries to the rotation, he could begin the year as a starter before transitioning to the bullpen after reinforcements arrive.

Though the Yankees would hurt less than Keller signing with a National League rival, of which he has been linked to several.

How Badly Do Cubs Need Keller Back?

Brad Keller of Chicago Cubs throws pitch from right hand — Chicago Cubs relief pitcher Brad Keller (40) pitches against the Pittsburgh Pirates during the sixth inning at PNC Park. | Charles LeClaire-Imagn Images

As Chicago figures out what its pitching staff is going to look like, Keller remains the biggest question in terms of their most significant remaining free agents. The team has largely already started to take shape, with hopefully a major top-of-the-line rotation splash to come, but whether or not the right-hander returns feels significant.

Hoyer has done a wonderful job of finding value in under-the-radar waiver claims and minor league deals, with Keller being a chief example among them. However, retaining that found talent is how success is sustained in this league.

The price still has to be right, though, and if the Yankees truly are interested, along with other teams, in Keller as a starter, it will realistically be difficult to pull off a fair deal to keep him.

Things should keep developing this week with the winter meetings arriving, and it would not be a surprise to see Keller sign in the coming days. Time will tell if it's with the Cubs or somewhere else.

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