The Cubs bullpen was a strength for the Cubs in 2025 but with Andrew Kittredge returning to the Baltimore Orioles, Drew Pomeranz signing with the Los Angeles Angels and Brad Keller inking a two-year deal
with the Phillies, the late innings of Cubs games will look a lot different in 2026.
The Cubs have been busy adding potential high-leverage arms, including Phil Maton, you can read more about his signing here. Today I wanted to take a closer look at the bullpen after the Cubs added lefty Hoby Milner and re-signing lefty Caleb Thielbar.
It shouldn’t surprise Cubs fans that the team has basically sat out the highest end of the reliever market this free agent season. We can have a healthy debate about whether the Cubs should be in on top free agents like Edwin Díaz or Devin Williams, but nothing in the Jed Hoyer era indicates the Cubs will consider that market in their best interests. This year’s offseason has been a pretty typical Hoyer-Hawkins production with the Cubs reuniting with a guy who was both solid for them and cost-effective for another one-year deal in the 38-year-old Thielbar, plus adding a couple of guys from the Rangers who are both cost-effective and intriguing in Milner and Maton.
You may remember Hoby Milner from his Brewers days. I’m sure Craig Counsell does, and it is notable that he joins a crew of guys who are cycling through a second run with Counsell in Chicago. Ben Clemens at FanGraphs sums up his offerings and limitations nicely below:
Why, then, is his deal with the Chicago Cubs for just one year and $3.75 million? It’s because he’s an extreme lefty specialist, and that skill set generally comes with a limited market. Milner isn’t a traditional late-inning reliever, a matchup-proof flamethrower. He has enormous platoon splits, triple the league average for lefty pitchers over a fairly substantial sample. It’s for exactly the reason you’d expect: Milner throws sidearm and with little velocity, relying on a sweeper that he throws nearly half the time against lefties to tie them into knots.
Against righties, he has no plus options, so he mixes his bread-and-butter sinker/sweeper with a so-so four-seamer/changeup combination to at least give them a few things to think about. That plan does not work particularly well. Righties slugged .445 against him in 2025, and that’s actually lower than his career mark. That means that he resorts to walking them quite frequently rather than giving in. In his career, he has sported a 4.7% walk rate against lefties, verifiably elite, and an 8% mark against righties. He walked more than 10% of the righties he faced in 2025, in fact.
I expect the Cubs to deploy Milner in circumstances where there are a couple of dangerous lefties stacked in an inning, either to encourage the other team to slot in a less-impactful righty for a momentary platoon advantage or to take advantage of his splits. While Thielbar does have platoon splits, they aren’t quite of the same magnitude as Milner. For example, Milner’s wOBA against was .224 for left-handed batters and .353 for right-handed ones, while Thielbar produced a much more manageable .213 v. lefties and .253 v. righties.
As I wrote when Maton was signed, the Cubs likely think they can build on his strikeout breakout with the Rangers, although a friend from Pitcher List is less optimistic than I am about that possibility:
According to the crew at FanGraphs Roster Resource, that sets up the Cubs bullpen to have Daniel Palencia close again with Maton in an eighth inning role, Thielbar in a seventh inning role and the following pitchers slotted in behind them: Milner, Porter Hodge, Ethan Roberts, Ben Brown, and Javier Assad. I presume Assad is still in the mix for starting occasionally and slots into the long relief role. Of the other three names, Roberts and Hodge have both looked excellent some times and like they’d be better off in Triple-A at other times. I wouldn’t be surprised to see the Cubs attempt to upgrade either of those spots during the rest of the offseason.
Ben Brown is far and away the most intriguing name in the pen to my eye. The Cubs have tried for two seasons to make him work as a starter, but the two-pitch mix has not consistently yielded results in a starting role. In a bullpen, however, Brown could really thrive. It wouldn’t be surprising to see him quickly rise in the high-leverage reliever ranks as he settles into a new role.
The relievers still unsigned among the top 50 free agents according to MLB Trade Rumors are: Nick Martinez, Seranthony Domínguez, and Pete Fairbanks. As Al would say, we await developments.
