Cubs, Brad Keller Could Get Back Together for Two Years, But Probably Not for Three

[Matthew Trueblood]

Image courtesy of © Patrick Gorski-Imagn Images

The Cubs enjoyed a major free-agent success in each department of their roster in 2025. They signed Matthew Boyd to a two-year deal in late November 2024, and watched him emerge as their co-ace for much of the season. They picked up Carson Kelly in mid-December, and enjoyed his best season as a big-leaguer. Crucially, though, they also hit on multiple minor pickups in the bullpen. Most important among those was righty Brad Keller, whom they signed to a minor-league deal as a starter and who ended the year as their de facto closer.

Keller, 30, is a free agent again after earning $1.5 million in 2025. He'll get a much bigger payday this time, and as he enters the market, the big question is whether he'll land a two- or a three-year deal. FanGraphs, ESPN and MLB Trade Rumors agree that Keller is in line for an annual average value in the $11 million range, but whether that stretches for two years or three could make a big difference in the chances of a reunion between the Cubs and their unexpected relief ace.

President of baseball operations Jed Hoyer is a hardliner when it comes to reliever contracts. He's willing to embrace a bit of risk, but that has to come in the form of a free-agent deal he feels is rational. Otherwise, he's equally happy to let that risk take the form of building a relief corps with some lower-cost bets and some upside plays.

"We've offered some [long deals to free-agent relievers]." Hoyer said at the GM Meetings Wednesday in Las Vegas. "I haven't given one out. So, I mean, it's not my favorite thing to do. I think that I prefer, you know, shorter commitments in the bullpen. But I'd never say never, like I said, we offered some last year. We just didn't win the bidding. So it's not, it's not a hard and fast rule. But I think you can, you can guess that we're probably going to be more focused on shorter commitments."

The big deals he alluded to offering last year were to Tanner Scott, on whom the Cubs were willing to go to four years and roughly $70 million; and Kirby Yates, on whom the Cubs were ready to offer a second year but who preferred the Dodgers even on a one-year pact. While even a two-year deal at an eight-figure salary for Keller would come with a bit of sticker shock, it would be a very palatable alternative to a Scott-level deal for someone like Robert Suarez, of the Padres.

One source familiar with the Cubs' thinking said the team considers Keller a priority winter target, but that they're very unlikely to stretch beyond two guaranteed years. A mutual or vesting option could be a way to satisfy both sides, if Keller is open to coming back. By every indication, he enjoyed his season with the team and would be happy to return, but this is the best chance he's likely to get at a major payday, so money will be a major factor.

It's possible the Cubs would go further on AAV to keep it to a two-year deal. They might guarantee $25 million over that term, but balk at $34-35 million over three years. Creative structures (like the aforementioned mutual option, which would come with a buyout) could keep the annual real cost of Keller down for them, and the team is unlikely to exceed the competitive-balance tax threshold in 2026, so his AAV doesn't matter as much as the real dollars. Spreading money across a longer term doesn't hold much appeal for the Cubs, when it comes to Keller. They would want to get a shorter-term deal done.

If a team steps up with an offer that bakes in some hope for Keller returning to a starting role, the Cubs will surely be outbid. He does have five pitches, which worked in concert beautifully in 2025. He's started so much during his career that some faith in his ability to return to that role is rational. A brief survey of sources in other front offices, however, found no team currently considering Keller as a candidate for a conversion back to the rotation. He's likely to make about $12 million, over either two years or three. If it be the former, there's a good chance the Cubs will be the team who signs him. If not, the odds tilt toward the righty finding a new home—and Chicago being left to chase still more bullpen help.

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