As baseball’s postseason marches on, the Cubs are forced to start their offseason work much earlier than hoped.
Expectations won’t change for 2027; this will still be a team with World Series goals.
But Jed Hoyer’s front office has a lot to do to make next year’s team better equipped than the one that was rapidly bounced from the playoffs.
Here are four of the biggest questions facing Hoyer & Co.
Hoyer might have to replace his entire starting rotation, with lefties Matthew Boyd, Shota Imanaga and David Peterson, as well as righties Clay Holmes and Kevin Gausman, all likely heading to free agency.
Might any return?
“I’ve been very fortunate to be a Cub and to have had an opportunity to be part of this ballclub,” Boyd said last week. “I believe my best is still ahead of me. I hope it gets to be here.”
At one point, Holmes looked like a prime candidate to go from trade-deadline rental to rotation cornerstone, but he struggled down the stretch and didn’t pitch in the playoffs.
Hoyer still described Holmes as someone “who fits our team really well,” a ground-ball guy with the best defense in baseball behind him.
Regardless of whether any return, though, expect the Cubs to spend on arms this winter.
“It’s safe to say that the biggest part of our focus going into the offseason is going to be on pitching,” Hoyer said Friday. “Whether that’s 100-to-0, what that ratio is going to be, has not been determined yet. But certainly, the great majority of our focus is going to be on pitching acquisition going in.”
That pitching focus could also include a bullpen overhaul.
The Cubs signed a lot of relievers last winter, and it didn’t work out, certainly not the way it did in 2025, when the team’s back-end relief group was a strength.
“I did a poor job on the bullpen this year, full stop,” Hoyer said. “We didn’t get it right, and that’s something we’ve spent a lot of time talking about already and we’ll continue to talk about.
“I take responsibility for that, and it’s something we’ll look to improve on this offseason.”
Daniel Palencia, Phil Maton and Shelby Miller are under contract for next season, while the team has option decisions to make on Colin Rea, Javier Assad and Jacob Webb.
Given Hoyer’s poor self-evaluation, it seems anything is possible on that front.
It’s not just pitching Hoyer will have to sort out.
Happ, the longest tenured Cub, is a free agent, and after a season that, statistically, did not match up with previous ones, whether he returns is a mystery.
That alone was enough to send Happ’s teammates to tears.
“He truly embodies what it means to wear the jersey,” shortstop Dansby Swanson said. “He embodies the Cubs more than anyone I know.”
“He is the Chicago Cubs,” center fielder Pete Crow-Armstrong said.
Happ has seemingly braced himself for the potential end to a decade-long stay on the North Side.
“All I can say is that I love being a Cub,” Happ said. “I’ve loved my time. I’ve loved the place, the people, Wrigley Field, the fan base. And it’s been truly special. I don’t think there’s a better place in baseball to play.”
Hoyer spoke glowingly of Happ on Friday but forecasted coming conversations rather than a firm decision.
Suzuki, too, is a pending free agent after five Cubs seasons, expected to be among the top hitters on the market, potentially opening up another hole in the outfield.
There are potential answers to these questions already on the roster.
But how good of solutions are they?
In the rotation, righties Cade Horton and Ben Brown, plus lefty Justin Steele, could make for an intriguing nucleus. But all three will be coming off significant injuries that wiped out most or all of their 2026s.
“It does prevent a bit of a team-building challenge,” Hoyer said. “All three guys have a real chance to impact us next year, but how much is a real question and we have to build accordingly.”
Two of this season’s reserves, utility man Matt Shaw and infielder Pedro Ramirez, could potentially help fill voids created by the departures of Happ and/or Suzuki.
The ability to backfill from within on that front would be helpful, should the Cubs allocate their resources with a focus on pitching.
“Having Pedro and Matt, super versatile, both really good players,” Hoyer said, “we can ask more of them going forward. We didn’t have to this year, given the nature of our corner outfield. But I think they both can certainly do that, and we’ll lean on both those guys more heavily going forward.”
