Earlier this month, upon the arrival of free agency, I wanted to send up some love for Brad Keller’s brilliant season out of the Cubs’ bullpen, and note how things might look for him (and the Cubs) in free agency. I don’t think any Cubs fans don’t want Keller back next year, all else equal, and I think the Cubs would agree.
My concerns on that front were two-fold, however, regardless of how the Cubs felt about Keller:
I have no doubt the Cubs would love to have Keller back, and I have little doubt Keller would love to stick around in a place where he had so much success and was well-appreciated. But you know the rub: Keller is likely going to get a healthy multi-year deal, and the Cubs just don’t sign guys like Keller to multi-year deals after big relief seasons.
… unless the Cubs see the potential to convert Keller back into a starting pitcher. He wouldn’t be the first former starting pitcher to kinda roam the wilderness for a bit, figure some things out in relief, and then go back to starting with some new tools in the toolbox (especially since he’s only 30). I think it’s a conversation worth having, though if Keller wants to go that route, he probably will find quite a few suitors out there willing to give him a shot. And, since he comes with the fall-back of relief, I could see some teams actually getting pretty aggressive to sign him to a deal that is a touch pricey for a one-year breakout reliever, but dirt cheap if he turns a corner as a starter (maybe three years and $36 million? Clay Holmes got three years and $38 million from the Mets to do a conversion – which largely worked – and he also got an opt out after the first two years).
That is to say, whether Keller lands a big multi-year deal as a reliever OR as a starter re-conversion, it’s hard for me to see the Cubs as the top bidder.
Then again, since we’ve seen rumors that the Cubs might actually pursue a higher-end reliever crop this time around, maybe the less likely return scenario of the two is the starter conversion? So maybe that’s the one to worry about more?
But is that even a realistic possibility? I was just speculating about a starter re-conversion at the time based on Keller’s profile and success.
Well, since then, the possibility of teams looking at Brad Keller as a starting pitcher conversion has popped up in multiple reports. I was not surprised for all the reasons I’d written previously, but now that it’s something of a reality, I thought it worth discussing.
Brad Keller as a Starting Pitcher Re-Conversion
Firstly, I won’t completely dismiss the possibility that the Cubs could be a team that would consider Keller for a conversion. They’re always on the hunt for starting pitching depth, and have shown no compunction about adding guys who might start or might be moved into the bullpen if the needs require. Maybe you sign Keller with a promise to give him a chance to stretch out in the spring, but no guarantee of a rotation spot when the rubber meets the regular season road.
All that said, the rumors have become pretty persistent that the Cubs are looking at a higher-tier of starting pitcher this offseason in free agency and trade, so it seems unlikely that they would prioritize Keller as a starting pitcher. If there are other clubs out there willing to do so, it’s not hard to imagine Keller going that route.
Although he has not been a full-time starting pitcher for several years, and there was a clear fall-off with the Royals that led to his move to the bullpen in the first place, it’s not as if he has never had success as a starting pitcher in the big leagues. It’s been a minute, sure, but he was a very good starting pitcher from 2018 through 2020, and he had brief periods of success thereafter as a part-time starter. He didn’t actually move fully into relief until 2024, the season following a procedure to address thoracic outlet syndrome.
Think about that timeline. He was a great young starter. Then went through a period of struggle. Then had surgery to address a physical condition that we know pitchers *can* pitch through, but typically not well. Then was converted fully to relief in his first year back after surgery, and didn’t get great results. Then, a full year removed from surgery, he joined the Cubs as a full-time reliever and things really clicked.
Did things really click for Keller because he found the right team and the right role? Or did things really click for Keller because he was finally feeling fully well again? If it’s mostly the latter, well, then why WOULDN’T he want to try starting again? And why WOULDN’T at least a few teams want to roll those dice?
Hypothetically, let’s say Keller has two paths available to him this offseason: maxing out a reliever deal at something like three years and $36 million, or signing somewhere he’s got a guarantee to be a starting pitcher for two years and $24 million. These are made up numbers just to set the stage. Would he choose to take advantage of his breakout 2025 relief season by maxing out his earnings right now, just in case things go sideways in 2025/2026? Or, knowing that capable starting pitchers can earn so much more than good relievers, would he take the shorter deal as a starting pitcher in the hopes that he could hit free agency again at age 32, coming off a couple seasons showing he can start again?
My guess is that some version of these conversations are happening right now behind the scenes with various teams. My related guess is that Keller and his reps are (smartly) probably trying to have it both ways: get that three-year deal from a team that is very likely to let him be a starting pitcher again out of the gate. I mean, I suppose I shouldn’t fully assume he wants to be a starter again, but, historically, former starting pitchers who move into relief are kinda always thinking in the back of their heads about a return to the rotation one day.
If it is possible for Brad Keller to thread that needle, I don’t think it’ll be with the Cubs. I could maybe stretch and see them willing to step waaaay outside their norm and sign a late-inning reliever to a pricey two-year deal. But going to a relatively pricey three years with a promise of starting, when the market is so full of compelling starting options (AND when you might be getting Shota Imanaga back anyway to take a starting spot), well, that’s hard for me to see even if I stretch.
That is all to say, as much as I or the Cubs might want Keller back in the bullpen in 2026, it may simply not be in the cards if it’s true that he’s being pursued as a starting pitcher by even a small number of teams.
We’ll see how long Keller’s market takes to shake out, because it’s possible it gets spurred along by the reliever market or the starter market, neither of which is quite yet cooking. The Cubs tend to like to hang around at the periphery on the relievers they do consider for big league deals, so maybe that’s what they’ll do with Keller in any case. And maybe he just doesn’t find the right deal out there, and maybe he appreciated his time with the Cubs so much, that the sides do ultimately decide to get back together and keep rolling with what worked so very well in 2025.
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