Two staples on the Chicago Cubs 2025 pitching staff have signed elsewhere, leaving the Cubs in need of quality innings in 2026.
The Chicago Cubs have strengthened their own bullpen this winter, bringing in names such as Phil Maton and Hoby Milner, and re-signing Caleb Thielbar. However, a pair of pitchers who really anchored the Cubs’ bullpen in 2025 have signed new deals with other clubs.
Drew Pomeranz
Sep 7, 2025; Chicago, Illinois, USA; Chicago Cubs pitcher Drew Pomeranz (45) throws the ball against the Washington Nationals during the first inning at Wrigley Field. Credit: David Banks-Imagn Images
LHP Drew Pomeranz reportedly signed a one-year, $4 million deal with the Los Angeles Angels on Tuesday. Pomeranz was in the minors when the Cubs made the trade for him. Once the lefty got to Chicago, he seemingly reinvented himself, showing he can still get it done in the majors.
In 57 appearances, Pomeranz sported a 2.17 ERA with 57 strikeouts. Although he only threw 49.2 innings in that body of work, the lefty generated a fair amount of swing and miss despite a lack of velocity. Pomeranz relied on just his two pitches, a fastball and a curveball, to become an effective lefty option out of the pen for Craig Counsell. In addition, Pomeranz’s 28.1% strikeout rate was in the 84th percentile in all of baseball, while his fastball run value was in the 85th percentile.
Pomeranz costed the Cubs virtually nothing, but became a dependable piece in the bullpen. As a result, he earns another contract after pitching last in 2021 before the 2025 season.
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Brad Keller
Oct 8, 2025; Chicago, Illinois, USA; Chicago Cubs pitcher Brad Keller (40) and catcher Carson Kelly (15) celebrate after defeating the Milwaukee Brewers in game three of the NLDS round for the 2025 MLB playoffs at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images
RHP Brad Keller was considered a bargain-bin signing for the Cubs in 2025. Once a starting pitcher, Keller failed to hang on as an every-fifth-day option as of 2022 and was relegated to the bullpen for a few seasons. The Cubs took full advantage of it, turning the righty into a weapon.
Keller made 68 appearances with the Cubs in 2025, pitching to a 2.07 ERA. Keller also added three saves and 75 strikeouts over 69.2 innings of work. The big righty was able to find his touch again, and now appears to be a name to watch for a long time.
As of Wednesday morning, Keller agreed to a two-year, $22 million deal with the Philadelphia Phillies, a huge payday for the former Cub. In fairness, he deserves it. Keller’s Baseball Savant page is loaded with dark red, indicating he was one of the best relievers in all of baseball last season. As a result, he gets a little bit of term and an eight-figure contract to boot.
What’s On Tap Next?
The Cubs have always been good with reclamation projects. Keller and Pomeranz and are both great examples of that. Maton, Milner, and Thielbar, along with names like Daniel Palencia and Porter Hodge, are a great start for the bullpen in 2026. That said, they’ll still need to fill in some holes with the departures of Keller and Pomeranz.