Cubs GM Drops Telling Brad Keller Hint Ahead of Free Agency

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Veteran pitcher Brad Keller was little more than an afterthought at this time last year.
He was coming off a 2024 campaign where he went 0-4 with a 5.44 ERA in just 41.1 innings pitched with MLB's two 'Sox' squads. Given that he hadn't had lower than a 4.57 ERA in each of the past three seasons, it would have seemed more likely that he'd be in the minor leagues than making an impact on a big league team in 2025.
But that could not have been less accurate. After signing a one-year, $1.5 million deal with the Chicago Cubs last offseason, Keller proved to be an invaluable asset out of the bullpen, amassing an elite 2.07 ERA and 75 strikeouts in 68 regular season appearances (69.2 innings pitched). He also produced a 1.59 ERA in five postseason outings, getting crucial outs in high-leverage scenarios for the club.

As a result of this success, not only is Keller's stock as a reliever high headed into free agency, but there have been reports that teams are even interested in converting him into a starting pitcher.
Cubs GM Sends Clear Message About Brad Keller Interest
One would imagine that the Cubs would prefer to have Keller as a reliever rather than a starter. But the bottom line is that they have every reason in the world to try and re-sign him this winter.
And this is the sentiment that Chicago general manager Carter Hawkins shared when speaking about Keller, which was included in a November 25 article from Meghan Montemurro of The Chicago Tribune.
Hawkins told Keller that the Cubs loved having him on board last season and would be keen to re-sign him to the squad next season. Hawkins then added, “We’ll see how it all plays out. Hard to say exactly where his market, our markets are going to be," but that Keller is definitely a guy that the Cubs will try and bring back this winter.
MORE: Cubs Linked To Ex-Rival Reliever As Bullpen Market Takes Shape
Brad Keller: Can I help you?
— Rob Friedman (@PitchingNinja) September 12, 2025
No thanks...we're just... 👀 pic.twitter.com/Ak5hhTurdu
None of this should come as a surprise, given what Keller meant to the Cubs' bullpen last season. Not to mention that the club has many relievers entering free agency and is in dire need to retool its relief corps.
Cubs fans are certainly hoping that Keller is back on the roster by Opening Day 2026. And given how his market is expected to shape up, one would imagine that he'd be back on a multi-year deal.
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Grant Young is a Staff Writer for On SI’s Chicago Cubs, New York Mets, Boxing, Indiana Fever, and Women’s Fastbreak sites. Before joining SI in 2024, he wrote for various boxing and sports verticals such as FanBuzz and NY Fights. Young has a bachelor’s degree in marketing and a master’s degree in creative writing with an emphasis on sports nonfiction from the University of San Francisco, where he played five seasons of Division 1 baseball. He fought Muay Thai professionally in Thailand in 2023, loves a good essay, and is driven crazy trying to handle a pitpull puppy named Aura. Young lives in San Diego and was raised in the San Francisco Bay Area.