The Chicago Cubs will be all about pitching, pitching, pitching this offseason. At least, that’s what they should be about.
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Although there should be concern over them potentially losing both of their corner outfielders (Ian Happ and Seiya Suzuki), their starting catcher (Carson Kelly), and valuable bench assets (Michael Conforto and Tyrone Taylor) to free agency, the biggest overall concern has to be pitching.
Chicago could very well lose their entire end-of-season starting rotation to free agency this offseason. The remaining starting pitching pieces are blanketed with doubt and injury concerns. If the Cubs are going to make a serious push for a real playoff run, they need to come up with lots of pitching answers this winter/spring.
They’ll have lots of money coming off the books—more than $100 million by most estimations. So, free agent pickups will probably account for the bulk of the incoming pitching. But it can’t all be about free agency. Jed Hoyer and the Cubs front office will need to make some trades to fill up the roster—and some of those trades may be uncomfortable ones.
Cubs-Mariners trade proposals
Sep 23, 2026; Seattle, Washington, USA; Seattle Mariners starting pitcher George Kirby (68) throws against the Houston Astros during the second inning at T-Mobile Park. Mandatory Credit: Joe Nicholson-Imagn Images
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James McKedy of Emerald City Spectrum, a Seattle Mariners blog, recently targeted the Cubs’ Matt Shaw as an ideal target for his team’s needs:
“The Cubs and Mariners are logical trade partners. Chicago could look to deal from its organizational position-player depth to strengthen its pitching staff, while Seattle has the rotation depth to improve its lineup without significantly compromising its ability to compete…
Seattle needs to make meaningful changes this offseason, with finding help at third base being near the top of the list. Given their starting rotation questions, the Cubs could be an ideal trade partner, and both front offices should explore whether a deal could improve their chances of contending in 2027.”
McKedy offered two trades proposals that could bring Shaw to the Mariners.
In one, the Cubs would send Shaw to Seattle for right-handed starter Emerson Hancock and No. 21 ranked prospect, RHP Lucas Kelly.
In the other trade proposal, Chicago would swap Shaw and No. 11 prospect INF James Triantos for right-handed starting pitcher George Kirby.
Starting pitching for Matt Shaw
Jun 20, 2026; Seattle, Washington, USA; Seattle Mariners starter Emerson Hancock (26) delivers a pitch second inning against the Boston Red Sox at T-Mobile Park. Mandatory Credit: Stephen Brashear-Imagn Images
Both trades would bring a young arm with years of team control immediately to the Cubs’ rotation.
The 28-year-old Kirby is the more established starter, with a 4.33 ERA last season through 30 starts and a career 3.73 ERA through 142 career starts. He’s under contract through the 2028 season.
Hancock, 27, posted a 3.57 ERA through 25 starts in 2026 and has a career 4.26 ERA over 301.1 big league innings. He’d be under team control through the 2030 season.
From a Cubs perspective, either would be a welcomed addition to a starting rotation currently in complete and total disarray. Losing Shaw would be tough, but not as tough as having to, again, watch a team built to win fall apart because of its pitching.
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