Cubs dodged a $22 million bullet after former reliever capitalized on breakout season

Last off-season, the Chicago Cubs saw a few members of their elite bullpen depart in free agency, while initially bringing back only Caleb Thielbar on a one year, $4.0 million deal. Meanwhile, Drew Pomeranz, who is now back in the organization, originally signed a deal with the Los Angeles Angels whereas Brad Keller got a massive two year, $22.0 million deal with the Philadelphia Phillies.

For Keller, he capitalized on this large deal by breaking out with Chicago in 2025. He went from an unexpected roster addition to a high-leverage arm, where over 68 outings he recorded 25 holds, three saves, and a 2.07 ERA. This was a drastic improvement compared to his career numbers, which consisted of an ERA over 4.00 at that time.

Unfortunately, his time in Philadelphia may already be over after just 32 games and 31.1 innings pitched as he has suffered a UCL tear. Keller is getting a second opinion on the matter, but if he undergoes surgery he will miss the remainder of this season and potentially all of the 2027 season.

The Chicago Cubs dodged a $22 million bullet by not re-signing Brad Keller

Chicago Cubs, Brad Keller — Oct 11, 2025; Milwaukee, Wisconsin, USA; Chicago Cubs pitcher Brad Keller (40) pitches against the Milwaukee Brewers in the eighth inning during game five of the NLDS round for the 2025 MLB playoffs at American Family Field. Mandatory Credit: Michael McLoone-Imagn Images

While the Cubs did make a notable addition to their bullpen last offseason by signing Phil Maton to a two-year, $14.5 million contract, they were ultimately wise not to match the Phillies’ commitment to Keller. Philadelphia remains on the hook for the $22 million guaranteed in his deal, regardless of whether he throws another pitch for their organization.

Instead, Chicago allocated its resources more efficiently, such as signing Hoby Milner and Jacob Webb while taking fliers on guys like Trent Thorton, who is now pitching in the big leagues after originally signing a minor league deal with the club. That is all to say that in hindsight, passing on Keller looks like one of the smarter decisions the organization made last offseason.

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