The Chicago Cubs' offseason plan is starting to come into focus - and it’s clear the front office is prioritizing a serious upgrade to the starting rotation. Shōta Imanaga is back in the fold after accepting the qualifying offer, but he’s likely slotted into the back end of the rotation. That’s not a knock on Imanaga - he’s a solid contributor - but the Cubs are clearly aiming higher as they look to land a true frontline starter.
The early part of that plan saw the Cubs take a swing at Dylan Cease. They were in the mix, but when the bidding pushed toward the $200 million mark, the Cubs pulled back, and Cease ended up signing with the Toronto Blue Jays. It was a calculated decision by Jed Hoyer and the front office - one that suggests they’re willing to spend, but not at any cost.
With Cease off the board, the Cubs have pivoted to Japanese right-hander Tatsuya Imai, a 27-year-old free agent who’s drawn interest from several big-market clubs. Imai is still very much in play, and from the Cubs’ perspective, he appears to be a top priority. But with competition heating up - and Hoyer’s reluctance to engage in prolonged bidding wars well-documented - there’s a real possibility the Cubs may need to move to Plan B.
And that’s where Michael King enters the picture.
King isn’t just a fallback option - he might be one of the smartest fits on the market for what the Cubs are trying to build. The former Yankees and Padres right-hander has been linked to Chicago since free agency rumors began swirling back in November. Now, as the Winter Meetings unfold in Orlando, King’s name is once again gaining traction.
Here’s why the fit makes sense: King’s profile aligns almost perfectly with the Cubs’ pitching philosophy. Over the past few years, Chicago’s player development system has leaned heavily into “cutting” fastballs - a technique that alters the pitch’s movement to create deception and induce weak contact.
No organization in baseball cut their fastballs more in the minors last season than the Cubs. King, whose cut fastball is one of his best weapons, fits that mold to a tee.
As Marquee Sports Network analyst Lance Brozdowski recently pointed out, King represents the type of pitcher modern front offices covet - one who can manipulate the baseball with elite spin and movement, creating a diverse arsenal of plus pitches. The Cubs aren’t just looking for velocity; they’re looking for movement, command, and adaptability. King checks all those boxes.
Of course, there are some concerns. King made just 15 starts in 2025 due to a shoulder issue, and he also missed time in 2022 with an elbow injury.
Durability is always a question mark with pitchers, and at 30 years old, King doesn’t come without risk. But then again, how many pitchers do?
The injury risk is baked into almost every free-agent arm - it’s more about whether the upside outweighs the uncertainty.
And with King, the upside is real.
Since transitioning to a full-time starting role in 2023, he’s made 54 starts between the Yankees and Padres, posting a 2.92 ERA over 284 innings with a strong 27.4% strikeout rate. That’s not just solid - that’s frontline production.
He’s shown he can handle the role, miss bats, and keep runs off the board. And he’s done it in two hitter-friendly environments.
Financially, the Cubs appear to be comfortable operating in the $100 million range for a starter - that much was made clear in their pursuit of Cease and continued interest in Imai. Depending on the length of the deal, King could fall into that range. He may not command the same dollar figure as Cease, but he offers a similar ceiling if he stays healthy - and perhaps even a better stylistic fit for what the Cubs are trying to develop on the mound.
According to reporting over the weekend, the Cubs’ interest in King is very real. He’s one of several arms the team has been connected to this offseason, and while he may have started out as the third option behind Cease and Imai, the more you dig into the numbers and the philosophy behind the Cubs’ approach, the more King looks like a potential perfect match.
He may not be the flashiest name on the board, but in terms of value, fit, and upside, Michael King could end up being the pitcher who helps take this Cubs rotation - and this team - to the next level in 2026.