The first point the Cubs try to make when recruiting a minor-league free agent pitcher is, though he may not be signing a major-league contract this offseason, the Cubs can help set him up for a more lucrative deal next year.
Former Cubs reliever Brad Keller’s story has become an integral part of that pitch.
Minor-league free agency doesn’t create much fanfare this time of year, with far flashier deals claiming the spotlight. But the Cubs’ approach to bullpen construction necessitates some wins in that category, in the vein of Keller’s breakout 2025 season.
With that performance as a springboard, Keller has reportedly agreed with the Phillies on a two-year contract worth $22 million.
The Cubs remained in contact with Keller and his agents at Excel Sports Management for much of his free agent process, according to sources. And though there was mutual interest in a potential reunion, Keller’s market progressed past the Cubs’ financial comfort zone.
Though it may not be much consolation to Cubs fans itching for their team to leverage its large-market status in free agency, Keller will continue to have an impact on the Cubs’ offseason. Now that his next contract is solidified, the Cubs have an impressive financial swing to point to in their minor-league free agent pitch.
The Cubs have surveyed all levels of the free agent reliever market this offseason. But a majority of their additions are expected to come through smaller deals — major-league contracts in the $1 million to $5 million range, minor-league signings, small trades, and waiver claims throughout the year.
“I’d rather spend our resources on areas of less volatility, honestly,” Hoyer said during winter meetings last week. “But at the same time, bullpens are really important. We’re not against [multiyear deals for relievers], but I do prefer the approach that we normally take.”
The Cubs have signed one reliever, right-hander Phil Maton, to a two-year contract, worth $14.5 million. But they have plenty more spots to fill. Their major-league bullpen additions since — left-handers Caleb Thielbar ($4.5 million with a 2027 mutual option) and Hoby Milner ($3.75 million) — have inked one-year deals.
The Cubs officially announced Caleb Thielbar’s re-signing this afternoon.
Source confirmed the one-year deal is worth $4.5 M guaranteed and includes a 2027 mutual option, as @PJ_Mooney first reported. https://t.co/bD67DrGB4r
— Maddie Lee (@maddie_m_lee) December 17, 2025
In order for the Cubs’ usual approach to work, they’re going to need some pleasant surprises from minor-league signings as well.
When the Cubs targeted Keller as a minor-league free agent last offseason, he’d posted an ERA over 5.00 in three of his last four major-league seasons.
A series of arm injuries from 2020 through 2023, including thoracic outlet syndrome, limited his playing time. And after undergoing surgery to address the condition, Keller bounced between the majors and Triple-A, with the White Sox and Red Sox in 2024.
Keller was, however, showing signs of delivery adjustment and untapped potential.
“Brad was probably tired of me [last] offseason,” then-special assistant Tyler Zombro quipped to the Sun-Times in early October. “When I took this job, if Brad wasn’t going to get a major league deal, I was like, we have to have Brad Keller.”
Zombro, who was heavily involved in the pitcher acquisition process even before the Cubs promoted him to vice president of pitching this offseason, highlighted Keller’s velocity potential, but also the supination that helped him manipulate the ball, and the action on his four-seam fastball.
“He’s pitched a lot in his career, but he’s still young — which is something I think is fascinating,” Zombro said. “He has the history, but he’s still moldable, which is hard to find.”
By the time Keller joined the Cubs in spring training, he’d taken another leap. His average fastball velocity shot up from 93.8 in 2024 to 97.2 last season. The Cubs also helped him tweak his slider and further developed his sweeper. But even Zombro didn’t foresee the level of success Keller would have in a high-leverage role.
Keller had been a starter for most of his career. His relief experience was mostly in multi-inning stints. So, in a new role after making the domestic opening day roster, he went through a series of firsts: entering a game with runners on base, consistently pitching back-to-back days.
“Really happy with how I’ve been able to bounce back, especially after two in a row, or even three out of four, four out of five, like, things like that — to be so resilient in that sense,” Keller said in late June. “… Just because there’s a lot of unknown when it comes to that.”
Keller was the Cubs’ setup man by mid-season. And by the end of the year, manager Craig Counsell was frequently calling on him in the ninth inning. Keller recorded 25 holds and three saves, while racking up a team-leading 68 appearances.
He held playoff opponents hitless in four out of five games, and still recorded a hold in the one exception against the Padres.
“It’s a fun group in here,” Keller said after the Cubs were eliminated in Game 5 of the NLDS. “This was the most fun I’ve ever had playing baseball. And it sucks that it’s over. We really felt like we had some bigger goals and bigger dreams.”
Keller and the Cubs will now be pursuing those dreams separately.
Keller is joining a club that’s become a perennial playoff contender in large part because of its willingness to be aggressive on the free agent market. And the Cubs, after ending a four-year-postseason drought, are looking to extend that success with what has so far been a more conservative financial approach.
