What the Cubs Need to Fix to Take the Next Step in 2026
The Chicago Cubs made their long-awaited return to the postseason in 2025, reaching October for the first time since 2020. But the celebration didn’t last long-they were bounced in the NLDS by the division rival Milwaukee Brewers. Now, with eyes on a deeper run in 2026, the Cubs have some clear areas to address if they want to go from playoff participant to legitimate contender.
Here’s a breakdown of three key issues the Cubs need to tackle this offseason-and why each one could be the difference between another early exit and a real run at the pennant.
1. Stabilize and Strengthen the Rotation
Down the stretch, the Cubs' starting pitching depth was tested-and exposed. Injuries and second-half regression left the rotation in flux at the worst possible time. Cade Horton showed flashes of future ace potential, but beyond that, things got shaky.
Shota Imanaga is the perfect example of that tale of two halves. His first 13 starts of the 2025 season?
A sparkling 2.40 ERA and a 0.92 WHIP-numbers that would put him in All-Star conversations. But his final 13, including the postseason, told a very different story: 4.79 ERA, 0.98 WHIP, and 18 home runs allowed.
That kind of volatility from a key starter is hard to overcome in October.
Imanaga is back in 2026 after accepting the Cubs’ qualifying offer, and Justin Steele is expected to return after missing nearly all of last season with an elbow injury. If both are healthy and effective, that’s a solid foundation.
But make no mistake-the Cubs still need a true No. 1 starter. Someone who can take the ball in Game 1 of a playoff series and go toe-to-toe with the best in baseball.
Without that kind of presence atop the rotation, they’ll be playing catch-up before the first pitch of October is even thrown.
2. Figure Out the Outfield-Fast
Kyle Tucker’s time in Chicago appears to be over. He declined the Cubs’ qualifying offer and looks poised to chase a long-term deal that likely exceeds what Chicago is willing to spend. That leaves a big hole in right field-and in the middle of the lineup.
Owen Caissie is the internal option most likely to step in, but there are question marks. In a brief 12-game stint last season, he hit just .192 with two extra-base hits. It’s a tiny sample size, sure, but it raises the question: is he ready to replace Tucker’s production, or is he still a year or two away?
There are other in-house possibilities. One route could be moving Seiya Suzuki back to the outfield full-time and handing the designated hitter role to Moises Ballesteros. That would get another bat in the lineup, but it also reintroduces Suzuki’s defensive limitations in the field-a trade-off the Cubs would have to weigh carefully.
Of course, there’s always the trade market. Both Caissie and Kevin Alcántara remain valuable prospects, and if the Cubs want to make a splash, they’ve got the assets to do it.
Whether it’s through free agency or a reunion with a familiar face, Chicago needs to solidify its outfield strategy soon. Tucker’s bat won’t be easy to replace, but standing pat isn’t an option if this team wants to keep pace in the National League.
3. Add Proven Infield Depth-Especially at Third
Last winter, the Cubs were linked to Alex Bregman and even reportedly offered him a $130 million deal. Bregman ultimately signed with the Red Sox, and the Cubs turned to top prospect Matt Shaw to handle third base. The rookie had a slow start but grew into the role, finishing with 13 home runs, 3.1 bWAR, and impressive defense in his debut season.
Now, Bregman is back on the market after opting out of his deal with Boston. Despite a second-half dip, he still posted a 128 OPS+, making him the top third baseman available in free agency. And with Tucker likely gone, the Cubs are going to need to replace a big chunk of offensive production.
This could be the Cubs’ second chance at Bregman-and it might make even more sense this time around. Signing a proven bat like Bregman would allow Shaw to shift into a utility role, giving the Cubs flexibility across the infield and providing much-needed depth. It’s not a knock on Shaw’s potential; it’s about giving the team options and raising the floor of the roster.
The Bottom Line
The Cubs took a step forward in 2025-but to keep climbing, they’ve got work to do. They need to add a true ace to anchor the rotation.
They need a plan-internal or external-to replace Kyle Tucker’s bat and glove. And they need to shore up the infield, ideally with a proven veteran who can produce from day one.
There’s a foundation here. Young talent is emerging, and the front office has the flexibility to make moves. But if the Cubs want to be more than just a playoff team in 2026, these three areas are where the offseason work has to start.