Rebuilding Chicago Cubs for 2026

Rebuilding Chicago Cubs for 2026

The Chicago Cubs won their first playoff series since 2017, but ultimately fell short in the divisional round against the Brewers. Now with the big off season ahead of them, can the Cubs hit all the right notes to take this team to World Series contenders? Hello, my name is Avery Taylor and welcome to Rebuild October, a series where we rebuild a new team every day across the month of October. So whether you’re looking for your favorite team or just generally curious as to how every team should approach the off season, then this is the series for you. And with that being said, let’s jump right into the video. As you can see from the war by position, the issues the Cubs need to address couldn’t be more set in stone. The offense was incredible in 2025, and with some more young talent rising up, it could be even scarier. While the pitching, especially the bullpen, really suffered. Can we find the right pieces on the mound while maintaining this offense’s dominance? Ultimately, a lot of the storyline circling this team this offseason will be centered around Kyle Tucker, who the Cubs traded for from the Astros last off season. At first, this seemed like a pairing made in heaven. But in the second half of the season, Tucker struggled to stay on the field and wasn’t himself when he was there. Whether it has any fact to it or not, that seems to have put a bad omen on him resigning in the Windy City. And unfortunately, we’ll see him walk out the door in this rebuild. Sha Imananga has an incredibly confusing contract that could technically mean he becomes a free agent this off season. Effectively, Ian won’t clear the first hurdle to make that happen as the Cubs will opt into his three-year club option. While the performance was down in 2025, the two seasons combined proved that he is worthy of staying in Chicago. Andrew Kitridge will also be held in Chicago after the Cubs opt into his $9 million club option. Kitridge has been incredibly consistent across the last four seasons. And with the bullpen due for some fresh faces, he could certainly be a good returning piece to the puzzle. Joining him back in the bullpen will be Caleb Filbar. Filar had a career season at 38 years old in Chicago, and it should have been enough to prove his worth back on this team. It’s a very similar story for Brad Keller, who was starting to bounce around from team to team before he found success in Chicago in 2025. He posted incredible peripheral numbers as well. So, there’s definitely a world where this sort of production is replicable, and that’ll happen in Chicago. Colorado is the last true decision the Cubs have this offseason with the $6 million club option. Ria provides a really interesting skill set as the team’s swingman. And with some inning question marks, particularly early on in the season, Ria could provide that exact right amount of value that the Cubs need. And thus, they’ll welcome him back to the pin to start the year. For the final ad back to the bullpen, they’ll return Taylor Rodgers. Rogers has been incredibly consistent over the past three seasons, posting a 3.16 RA in that time while striking out 10 batters for nine innings. His stent in Chicago hasn’t been the best, especially with how many homers he got rocked for. However, that’s not a consistent problem in his career, and I expect it to self-correct next season. However, the Cubs won’t be done adding to this bullpen because they’ll swing a trade with the Los Angeles Dodgers for Blake Dryen, as well as prospect Chase Harland in exchange for Matthew Boyd. Trident was not near the lockdown reliever that we’ve come to know over the past few seasons. He uncharacteristically let the hits and walks get away from him, and that’s always a recipe for disaster. However, he still strikes out a ton of batters and the homer should go down in Chicago. So, this has the makings of being a steal. As for what they lost, Matthew Boyd seemingly came out of nowhere to become the team’s number one option down the stretch. He had a good stint in Cleveland prior to signing in Chicago, but it was just eight starts, and I don’t think anyone expected him to do what he did in 2025. However, with that in mind, this could be a great time to sell high on the left-hander. The Cubs have a ton of middle of the rotation type pitchers and they need to move off one to allow them to get a true ace in free agency. However, before we talk about free agency, we have to talk about the prospects on the way and the Cubs have a ton of exciting young talent. Owen Casey is the highest rated of the bunch defined by big-time pop and a strong arm. Casey profiles well in right field for the future, but has been roadblocked for some time. In two seasons at AAA, he has an 887 OPS while averaging over 20 homers a season there. Eventually, the Cubs forced him onto the roster, but he had a lackluster 12 games and struck out over 40% of the time. It’s an incredibly small sample size, and we’re counting on him to find that stroke in Chicago as their fourth outfielder. Traditionally, I hate putting high rated prospects on the bench, but he’s mashed at AAA enough already. Moyas Bisteros had a similar track to his career where he matched at AAA enough that they just had to say enough is enough. Unlike Casey, Bisteros was able to replicate his success in the major leagues, posting an 868 OPS across his 20 games. He’s technically a catcher and he certainly has the arm to make it work. But the rest of his catching skills just do not. However, at 5’8 and with below average speed, he’s very limited in where he can play. So, he will be probably a permanent resident at the age, which is what he’ll do versus right-handers in 2026. Jackson Wing still has some work to prove in the minor leagues after just three unimpressive starts at AAA. He has an incredible fastball slider and change up mix, but that comes with some control issues. However, in 2025, he was able to shave nearly a walk and a half off per nine innings against harder competition and at the same time actually improved his K per nine. If he can continue that trend, there is no doubt that he’ll crush Triple A. And the only question will be when can he crack the major league roster. Kevin Alcantara probably has one of the highest ceilings of any prospect in baseball. Tons of pop, can run well, and with a good arm, he can play center field, and does it all from a 66 frame. The hit tool is the biggest question mark about his game, and that is evident from his nearly 30% strikeout rate at AAA. Despite that high K rate, he was still able to put up good numbers, and for that, he’ll start the season platooning at the H versus Lefties. I feel kind of bad for Jonathan Long, who’s had an incredible minor league career. In his three seasons, he’s actually posted an 878 OPS while averaging close to 20 homers over the past two seasons. He’s limited to just first base, which means he’s another blocked prospect. However, he’s just so talented with the bat that he has to find the major league field at some point. Finally, making it to the major league roster will return Carson Kelly behind the dish, Michael Bush at first, Nicoer at second, Swanson is short, Matt Shaw at third after a big second half of the year. The outfield left to right will be Ian Hap PCA and then Seyasa Suzuki when a righty is on the mound and then he’ll get moved to the H versus lefties. Miguel Amaya is the lone nonpros to return to the bench with one spot left to fill. The team needs a flexible infielder on a cheap deal and the team will find that in Dylan Moore. Moore isn’t flashy, but he’s a near league average bat and can virtually play every position on the diamond. That would be incredibly valuable, especially in raising the floor between the starters and backups. The rotation will return Kate Horton and Jameson Tyion on top of Immananga, leaving two spots left to fill. The less sexy of those two will be Justin Verlander with the signing. It’s important to note that this is essentially an open try out for Verlander, who’s wanting to pitch in his age 43 season. He had a strong second half of the year and might need to prove some more to find a true home that is looking to contend. The Cubs have the perfect situation where Justin Steel will miss the first portion of the year. While they also have a solid swingman and Rehea, they can afford to take a flyer on an old-timer like Burlander who’s still looking to prove he belongs. However, for the signing you are all looking for, it’ll come in the form of Shane Bieber. When Bieber is healthy, he is one of the best pitchers in baseball. Before his seventh starts to end the season in Toronto, I wasn’t sure he would decline that player option. However, he has proved he is still very, very good. The homers are the only concerning thing that are plaguing him, but again, that should drop in Chicago, and this could be the opportunity for the Cubs to get a true ace. The only unnamed returner to the bullpen will be Daniel Palencia after a breakout 2025. And then for the final spot on the roster as a whole, the Cubs need to get a lock down reliever, and they’ll find that in Ryan Hley. Aside from him tormenting Met fans for 22 games, Helley has been incredible since his breakout season for the Cardinals back in 2022. that three-year stretch from 2022 to 24, he was able to post a 1.83 RA. If you can find that sort of success in Chicago, it’s a completely worthy addition. And that’s going to do it for the video. The Cubs don’t need a whole lot to be true contenders. They just need to have a few tweaks, fix up that bullpen, and maybe get a true ace, and they are right there in the mix. I hope you guys enjoyed it. Thank you guys for watching, and have a wonderful day.

The Chicago Cubs were bounced in the divisional round, creating a dynamic offseason where they can take this roster in a number of directions. Will they be able to resign Tucker, or allocate that money to other points of the roster?

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