Brad Keller didn’t just bounce back in 2025 – he reinvented himself. After a rough 2024 that saw him struggle with both the White Sox and Red Sox, the right-hander entered the Cubs’ spring training on a minor league deal, fighting just to stay in the league. By the end of the season, he wasn’t just a feel-good story – he was the most valuable reliever in Chicago’s bullpen, and arguably one of the most reliable arms in the National League.

Now, that remarkable turnaround is setting the stage for a potentially significant payday in free agency – and it could mean the Cubs are about to lose their best bullpen weapon.

Keller’s transformation wasn’t just about numbers, though the stats speak for themselves. A 2.07 ERA, 0.96 WHIP, and 75 strikeouts across 68 appearances is elite-tier production.

But what stood out even more was how he climbed the bullpen ladder. He started the year in middle relief, worked his way into high-leverage spots, and by the end of the regular season, he was closing games – including in the postseason.

That kind of trust from manager Craig Counsell doesn’t come easy.

It’s a long way from where Keller was just a year ago. Once a promising starter with the Royals, his career had seemingly stalled out before 2025.

The Cubs gave him a shot, and he responded by completely overhauling his approach. He ditched the starter’s mindset, leaned into his strengths as a short-burst power arm, and found a rhythm that made him nearly untouchable in the late innings.

But success comes with a price – especially in free agency.

According to reports, Keller is drawing serious interest not just as a reliever, but also as a potential starting pitcher. That’s the kind of interest that changes the financial equation. Teams looking at Keller as a starter are going to pay starter money – and that could push him well beyond what the Cubs are willing to spend for a bullpen piece, even one as impactful as Keller.

This isn’t an isolated case, either. We’ve seen this movie before.

Pitchers like Clay Holmes, Reynaldo López, and Jordan Hicks followed similar trajectories – bullpen success leading to bigger opportunities and bigger contracts. Holmes landed a three-year, $38 million deal with the Mets.

López signed for three years and $30 million with the Braves. Hicks?

Four years, $44 million with the Giants. All three parlayed bullpen dominance into starter-level paydays or hybrid roles with significant financial upside.

Keller could be next in line.

MLB Trade Rumors recently ranked him No. 26 on their top-50 free agent list, projecting a three-year, $36 million deal. That’s a number that reflects both his value as a reliever and the possibility that a team might take a shot at stretching him back out into a rotation role. Given the scarcity of quality pitching on the market and Keller’s versatility, that projection feels realistic – maybe even conservative if the bidding heats up.

The Cubs, for their part, are reportedly more open to investing in bullpen arms this offseason than they have been in recent years. But there’s a difference between being open to spending and being willing to match starter-level offers for a reliever – especially one who just turned 30 and only has one season of elite relief work under his belt.

So what happens next?

If Keller’s market continues to trend toward starting roles and multi-year deals in the $30-40 million range, it’s hard to see the Cubs hanging on. They took a smart, low-risk gamble that paid off in a big way. But now, they might have to watch as another team cashes in on the version of Brad Keller they helped unlock.

It’s a tough spot for Chicago – losing a top-tier reliever is never easy, especially one who became such a key part of the team’s late-season success. But it’s also a testament to how far Keller has come.

From a minor league deal to a potential $36 million contract in less than a year? That’s not just a comeback – that’s a career resurrection.

Wherever he lands, Brad Keller has earned this moment. And for the Cubs, the challenge now is finding the next arm who can follow that same path.