We talk about the Chicago Cubs’ need this offseason for a front-half starting pitcher as if it’s a self-evident thing, primarily on the basis of things we saw during the 2025 season and postseason. When the Cubs lost Justin Steele early in the year, the front of the rotation thinned in an instant. When Shota Imanaga hurt his hamstring, and generally wasn’t the same guy we saw in 2024, the front of the rotation almost entirely evaporated.
That evaporation was softened considerably by the revelation that was the first half Matthew Boyd, and the emergence of Rookie of the Year runner-up Cade Horton. Of course, by the time September arrived, Boyd had worn down, and Horton was on the precipice of an injury that would take him out of the playoffs entirely.
From four “front-half” types to arguably none, right when the Cubs needed that type of pitcher the most. They were very fortunate to have great contributions from Jameson Taillon (who sure pitched like that guy down the stretch), Colin Rea (what a presence he was all year), and the bullpen, and they collectively did the best they could in September and October. But the best clubs tend to have enough front-half types to cover an entire playoff series, or at least most of one.
It’s not a criticism of the player performances, individually. It’s just an acknowledgement that there’s a pretty clear area where the Cubs could’ve been better late in the year and in the postseason. It helped create a hurdle that was a little too high to clear.
© David Banks-Imagn ImagesLooking ahead to 2026, it was unreasonable to operate as if this issue would not be an issue going forward. Maybe Justin Steele will return in June as JUSTIN STEELE, but maybe he won’t. Maybe Shota Imanaga will return to his 2024 form, but maybe he won’t. Maybe Matthew Boyd will repeat for most of the year, maybe he won’t. Maybe Cade Horton will be the ace he looked like he could be, or maybe he’ll have a sophomore adjustment period.
The Cubs do have strong starting depth as far as big-league-ready types go, but Javier Assad missed a lot of time, the Cubs haven’t given Jordan Wicks a consistent starting look in a long time, and Ben Brown hasn’t quite clicked as a starter. Is it reasonable to expect any of those three to be clear front-half starting pitchers for the big league Cubs in 2026? I hope for it. I can imagine it. But should the Cubs expect it? No.
Thus, heading into the offseason, it was obvious that the Cubs could use another front-three-ish starting pitcher. There wasn’t really a need to dig too much deeper than that.
But, with another option in Tatsuya Imai off the board, and the other options dwindling, I’m going to dig a little bit more anyway. Because, seriously, the Cubs need to add another quality starting pitcher, and I’m good with pressing on every possible reason.
Let me make explicit an additional reason for adding a front-half starting pitcher this offseason, when so many were available: the Cubs’ long-term pitching situation internally looks more than a little concerning.
The Cubs Organizational Need for Pitching and the Impact of This Offseason
I won’t belabor the underpinning point here, because we’ve discussed it many times. In short, outside of Jaxon Wiggins, the Cubs’ farm system is in a really rough spot on the pitching side. Yes, there are some guys with big league potential. Yes, there are some younger, upside types. But overall, in terms of clear future big league contributors, much less guys who can be front-half types in the next year, it might be one of the roughest systems in all of baseball.
Some of that is due to a fall off in scouting and player development since Craig Breslow’s departure for the Red Sox, where he’s made a huge impact on their pitching infrastructure. Some of that is due to the Cubs getting almost nothing on the pitching side out of International Free Agency over the last decade. Some of that is due to injuries. Some of that is due to promotions. And some of that is due to trades. There are a lot of contributing factors, some of which are blameworthy and others of which are just the way things go; but, regardless of the reason, the Cubs cannot count on getting a whole lot of impactful contributions to their big league rotation if things really go sideways this year on the injury front.
Consider, too, the contract situations of the guys currently in the big league rotation. Justin Steele has two years of arbitration left. Shota Imanaga is a free agent after this season. Jameson Taillon is a free agent after this season. Matthew Boyd is a free agent after this season.
Now combine those two things: virtually no obvious near-term front-half starting pitcher types percolating up over the next year (outside of, hopefully, Jaxon Wiggins), and virtually all of the big league rotation set for free agency over the next year or two.
Yikes!
Now imagine Cade Horton gets hurt, or Jaxon Wiggins doesn’t work out, or none of Javier Assad, Jordan Wicks, or Ben Brown pitch even like mid-rotation guys in 2026.
Are the Cubs, uh, prepared to rebuild the entire rotation after 2026/2027? Is that even possible?
Which brings me back to this offseason, and the already-obvious need to add a front-three starting pitcher for all the original reasons that were clear as soon as the postseason ended. From here, if you add a multi-year starting pitcher, you not only improve regular season performance and depth for 2026, and you not only might improve your postseason performance, but you also provide yourself more overall organizational coverage for 2027 and beyond, depending on the structure of the deal (or the control of the acquired pitcher, if a trade).
The Cubs talk a whole lot about covering innings. The need a certain number of innings each season, and they are happy to use a combination of starters, swing-guys, and relievers, from all areas of acquisition, to cover those innings. But the process of planning to cover those innings in 2027 and 2028 cannot begin only just before those seasons start. If you’re doing it right, these are long-term planning processes, full of optionality and back-up plans and upside shots and downside protection. Right now, the Cubs have almost none of that beyond 2026.
That is way, together with the impact for 2026, it is critical that the Cubs add a competent, quality, front-three starting pitcher this offseason, when so many of them were available. This is why I’d probably be much more happy about, for example, even a Zac Gallen signing than some folks might be. It’s not quite a “beggars can’t be choosers” situation, but it’s close.
Failing to do that, the Cubs will be left with adding – at best – a mid-rotation hail mary (hoping for another Boyd situation), and then figuring out how to cobble together more long-term coverage another way.
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