The Chicago Cubs, by most accounts, will be players in the free agent market when it comes to starting pitching this offseason.
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The question, however, is to what degree they’ll be players.
There’s already plenty of buzz about the Cubs’ interest in former Cub top prospect Dylan Cease, who will be moving on from the San Diego Padres via free agency. Japanese import Tatsuya Imai has also been a name tossed about by media. To a much lesser extent, Framber Valdez has been mentioned as a good fit for the Cubs’ needs as well.
But it could also be very possible– some people would say, likely– that Chicago could target starting pitchers from the second tier of the 2026 free agency talent pool. It would certainly be in character for the frugal Cubs to try and take a riskier stab at a front-of-rotation arm for less money and/or a shorter contract.
Chicago Cubs interested in other Padres free agent starter
Sep 16, 2025; New York City, New York, USA; San Diego Padres starting pitcher Michael King (34) delivers a pitch during the first inning against the New York Mets at Citi Field. Mandatory Credit: Vincent Carchietta-Imagn Images
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If that is the objective this winter, a recent report in The Athletic, regarding the Cubs’ interest in former Padres starter and free agent Michael King, makes a lot of sense.
Via the collaborative piece by Sahadev Sharma and Patrick Mooney:
“Michael King is another pitcher the Cubs have on their radar, viewing him as a starter with big upside when healthy. His work ethic, intelligence and feel for pitching are attributes that the Cubs previously targeted with free agents such as Jameson Taillon and Matthew Boyd.
King’s right shoulder became an issue this year, limiting him to just 15 starts with the San Diego Padres. In terms of process, the Cubs can point to their work with Michael Soroka this year. It’s not a perfect example — Soroka went on the injured list with a shoulder problem almost immediately after the Cubs acquired him at the trade deadline. But by the end of the season, Soroka had made some slight delivery tweaks and boosted his velocity back toward peak levels.”
Michael King as the new Matthew Boyd?
MLB: Kansas City Royals at Chicago Cubs Jul 22, 2025; Chicago, Illinois, USA; Chicago Cubs starting pitcher Matthew Boyd (16) delivers a pitch against the Kansas City Royals during the first inning at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images
The right-handed King, who the Cubs reportedly asked about at the trade deadline last season, declined his part of a $15 million mutual option and is expected to also turn down the Padres’ $22 million qualifying offer.
Although an elite-tier starter when healthy, King struggled with staying on the field last season. He only managed 15 starts in 2025 while dealing with a nerve issue in his right shoulder and a subsequent knee injury. He would finish the year with a 3.44 ERA over 73.1 innings. In 2024, his first full year as a starter after transitioning from the bullpen, he registered a 2.95 ERA over 173.2 innings.
Some feel that the 30-year-old King could be had on a deal similar to the one the Cubs used to sign Matthew Boyd (two-years, $29 million) last season, although probably at a higher AAV, maybe in the neighborhood of $18-19 million per season.
The thought is that King, much like Boyd, might be available on a shorter contract as he proves that he can stay healthy and replicate past success.
A good fit for both parties
Chicago Cubs president of baseball operations Jed Hoyer speaks before introducing Craig Counsell as new Cubs manager during a press conference in Chicago. Mandatory Credit: Kamil Krzaczynski-Imagn Images
If this free agency run is all about proving himself fit for a more lucrative contract down the road, King could do a lot worse than signing on with the Cubs, who have a good reputation for rehabbing arms and facilitating pitching comebacks.
If the Cubs lose out on King, but are still determined to go after King-like projects on Boyd-like deals, there will be many names from which to choose this offseason. Brandon Woodruff, Merrill Kelly, and Chris Bassit, among others, could be fits. King, however, would be the youngest of the bunch and the one with the least mileage.
It’s still very early in the offseason, though, and a lot could happen that might deviate the Cubs from their plans. At the very least, this is a positive sign that the team is actually looking to improve its pitching with some new blood.
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