This story was excerpted from Jordan Bastian’s Cubs Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.
CHICAGO — The Cubs achieved a number of goals this past season. The ballclub ended its postseason drought, won a playoff series and had Wrigley Field rocking again with its intimidating October environment. The next step for the team is to make this a regular event and to keep pushing for more wins and a division title.
“We need to constantly raise our level and get to that point where we can do that year in and year out,” Cubs president of baseball operations Jed Hoyer said. “We have a really good foundation to build from. We just need to continue to focus on making good decisions and building from that foundation.”
Here are five questions facing the Cubs this offseason:
1. Is there a chance Kyle Tucker is back with Cubs in ‘26?
The Cubs knew it might very well be a one-year arrangement when they swung the blockbuster trade with the Astros in December to add Tucker to the lineup. Tucker is 28 years old, ranks 11th in MLB in bWAR (25.4) over the past five seasons and is arguably the best all-around hitter on the free-agent market this winter.
The odds seem to point toward Tucker signing elsewhere, but the Cubs would certainly have an edge on the recruiting side of things. He just spent a season with the ballclub, getting familiar with the organization, teammates, staff, facilities and city. There is nothing to sell Tucker on from that perspective.
Will that make a difference?
“We’ll see what happens,” Tucker said after the Cubs were eliminated from the playoffs. “I don’t know what the future is going to hold. If [I sign elsewhere], it was an honor playing with all these guys and I wish everyone the best of luck.”
The quick version on Imanaga’s situation is that the Cubs have to decide whether to pick up a three-year, $57.75 million option that covers the ‘26-28 seasons (he earned a $250,000 bonus per year for his fifth-place finish in the ‘24 Cy Young race). If Chicago declines, Imanaga can choose between a $15.25 million player option for ‘26 or declining that and going the route of a potential one-year qualifying offer (likely north of $22 million). No matter how the sides proceed, the most likely outcome is Imanaga returns for at least one more season.
Given the cost of starting pitching, this seems like a no-brainer for the Cubs to just pick up the three-year option. Just last offseason, Chicago signed Matthew Boyd for a two-year deal worth $29 million guaranteed after the lefty logged just 11 starts between the regular season and playoffs. The cost of starting pitching is high, so an average of $19.25 million for Imanaga over three years looks like a good deal.
That said, Imanaga is 32 years old and just had a tough finish to his season with homer issues. For the Cubs, they will have to weigh the larger track record against the smaller-sample finish. To that end, the lefty had a 2.75 ERA with 1.4 homers per nine innings in his first 42 starts (248 1/3 innings) in MLB, versus a 5.17 ERA with 2.6 HR/9 in his last 12 (69 2/3 inning).
3. What will the biggest need be this winter?
Lefty Justin Steele (left elbow surgery in April) is on a path to return early next season, so that is good news. Horton is coming off a fantastic rookie year, and Imanaga, Boyd, Colin Rea ($6 million club option) and Javier Assad could all be back. Beyond that, the Cubs have to sort out how Ben Brown and Jordan Wicks fit into the picture (bullpen or rotation). Maybe prospect Jaxon Wiggins (No. 67 on Pipeline’s top 100 list) breaks through in ‘26, too.
That seems like a solid place to start for the Cubs, but they could really use an impact arm added to the top of the list. There will be some solid rotation pieces in free agency (Framber Valdez and Dylan Cease heading that class), but expect Chicago to also explore the trade front, perhaps circling back on talks that fell apart at the Trade Deadline.
4. How will the Cubs rebuild the bullpen?
By the end of the year, the Cubs’ main late-inning arms were Daniel Palencia, Brad Keller, Andrew Kittredge, Caleb Thielbar and Drew Pomeranz. Only Palencia is under control for ‘26. Keller, Thielbar and Pomeranz are set for free agency, while the Cubs have a decision to make on Kittredge ($9 million club option). Michael Soroka, Taylor Rogers, Ryan Brasier and Aaron Civale are also among the Cubs upcoming free-agents.
The Cubs have gone through mid-season makeovers of their bullpen in each of the last two years, bringing in reclamation projects and experienced veterans via trades, claims and signings to fill in gaps around some of the younger, in-house options. Expect that to continue to be a trend for Hoyer, who has leaned against long free-agent deals for relievers (last winter’s pursuit of Tanner Scott being an exception).
5. Where could the Cubs add offense?
Even with Tucker potentially exiting in free agency, the bulk of the Cubs’ starting lineup is locked into place. Seiya Suzuki could move to right field from designated hitter, opening up possible playing time for Top 100 prospects like outfielder Owen Caissie (No. 47) and catcher Moisés Ballesteros (No. 53). If the Cubs want to bring in an impact bat from the outside, there will likely need to be a trade or two to loosen the inflexibility of the projected starting group.
