The Cubs' bullpen was a steady hand in 2025, but heading into 2026, the late innings are getting a makeover. With Andrew Kittredge heading back to Baltimore, Drew Pomeranz signing with the Angels, and Brad Keller landing a two-year deal with the Phillies, Chicago’s relief corps is going to have a new look-and a different feel.
But the Cubs haven’t been sitting on their hands. They’ve been busy reshaping the pen, not with splashy, top-dollar names, but with arms that fit their mold: cost-effective, experienced, and potentially high-upside.
The additions of Phil Maton, Hoby Milner, and the re-signing of Caleb Thielbar are classic examples of the front office’s approach under Jed Hoyer and Carter Hawkins. This isn’t about chasing the biggest names on the market like Edwin Díaz or Devin Williams.
It’s about building a bullpen that can be flexible, matchup-savvy, and deep.
Let’s start with Hoby Milner, a name Cubs fans may remember from his time with the Brewers-and one that new manager Craig Counsell certainly knows well. Milner brings a very specific skill set to the table.
He’s a lefty specialist in the truest sense, and that’s not just a label-it’s backed up by the numbers. In 2025, left-handed hitters managed just a .224 wOBA against him.
That’s elite territory. But flip the matchup, and the picture changes: righties tagged him for a .353 wOBA, and slugged .445 off him last season.
Milner’s arsenal explains the dramatic splits. He throws sidearm with minimal velocity, leaning heavily on a sweeper-nearly half his pitches to lefties-to keep them off balance.
Against righties, he doesn’t have a go-to weapon. Instead, he mixes in a sinker, a so-so four-seamer, and a changeup in an attempt to keep hitters guessing.
The results? Inconsistent.
He walked more than 10% of the righties he faced in 2025, a big jump from his career average of 8%.
So what’s the plan here? Expect the Cubs to use Milner strategically-think mid-inning situations where a couple of tough lefties are due up.
He’s not going to be a traditional setup man or closer, but in the right spots, he can be a real weapon. And if he can force opposing managers to burn a righty pinch-hitter just to avoid a bad matchup, that’s a win too.
Thielbar, who’s back on another one-year deal at age 38, offers a bit more balance. His 2025 splits were solid across the board: a .213 wOBA against lefties and a respectable .253 against righties. He doesn’t have Milner’s extreme platoon profile, but he’s dependable, knows how to pitch, and fits nicely in a seventh-inning role.
Phil Maton, another recent addition, is one to watch. The Cubs are likely hoping to build on the strikeout surge he showed with the Rangers.
He’s not overpowering, but he’s crafty and can be tough to square up. If that swing-and-miss stuff sticks, he could slot into a key eighth-inning role.
According to projections, the Cubs’ bullpen hierarchy is starting to take shape. Daniel Palencia is expected to close, with Maton setting him up in the eighth and Thielbar handling the seventh. Behind them, it’s a mix of intriguing arms and unproven depth: Milner, Porter Hodge, Ethan Roberts, Ben Brown, and Javier Assad.
Assad is likely to bounce between long relief and spot starts, depending on how the rotation shakes out. As for Hodge and Roberts, both have flashed potential, but consistency has been elusive.
At times, they’ve looked like they belong in a big-league bullpen; other times, Triple-A has seemed more appropriate. Don’t be surprised if the Cubs look to upgrade one or both of those spots before Opening Day.
And then there’s Ben Brown. He’s the wild card in this group-and maybe its biggest upside play.
The Cubs have spent the last two seasons trying to make him work as a starter, but the results have been mixed. The two-pitch mix hasn’t held up well in longer outings.
But in a bullpen role? That’s a different story.
Shorter stints could allow his stuff to play up, and if he clicks, Brown could quickly climb the bullpen ladder and find himself in high-leverage spots.
The Cubs’ approach to the bullpen this offseason has been measured, not flashy. They’re not chasing headlines-they’re assembling a group that can give Counsell options, matchups, and depth. And while there’s still room for another move or two, the early blueprint is clear: build a bullpen that can adapt and evolve, even if it doesn’t come with All-Star names on the back of the jerseys.