For the second year in a row, the Chicago Cubs won one of the National League wild card spots and for the second year in a row, they were unable to turn that spot into a deep playoff run. Last year, they beat the Padres in the Wild Card Series in three games before being eliminated by the Brewers in the NLDS. This time around, they were swept in two games by the Padres in the first round.
In some ways, the Cubs had an incredibly fun season. There were two separate 10-game winning streaks from mid-April to early May, pushing the Cubs to an MLB-best 27-12 record. They then went on a 35-16 run from June 11 to August 12 and looked, once again, like a World Series contender. They had the best defense in baseball while scoring the most runs and leading the majors in OPS and position-player WAR. Pete Crow-Armstrong went 40-40 and will likely win the NL MVP with one of the greatest Cubs seasons ever – and one of the best for any team this century.
In another way, it was an incredibly frustrating group. While leading the majors in several player position statistics, the Cubs had the worst pitching WAR in baseball. Yes, even worse than teams like the Rockies and A’s. There were plenty of injuries, but also a ton of underperformance that just shouldn’t be acceptable for a team with the aspirations of the Cubs. Those two 10-game winning streaks? They were followed by 14 losses in the next 16 games, a streak that included a 10-game losing streak. The pitching really started to melt away in mid-August, which in part led to the Cubs finishing 17-22 after August 12. This fall meant losing home field advantage for WCS and having to travel to San Diego.
Perhaps to sum it all up, the Cubs led the majors with 13 wins without a win in 2026, but also lost 34 leads among their losses and had seven losses without a win.
As they look toward next year, here are three questions facing the ballclub.
1. How will the outfield corner spots evolve?
Right fielder Seiya Suzuki and left fielder Ian Happ are both heading to free agency, leaving huge holes in the lineup.
Happ, 32, is coming off his worst season since 2021 after a four-year streak between 3.5 and 4.3 WAR (he recorded 2.9 this year). His offense took a bit of a step back and the culprit was – as a switch hitter – his work as a right-handed hitter. He was still productive as a lefty, but on the right side he hit .145/.217/.267 with 52 strikeouts in 131 at-bats.
Suzuki, 32, has long been a productive, if inconsistent, hitter and has improved his defense this season to help him reach a career-high 5.1 WAR. Over his last four seasons at the plate he hit .270/.353/.480 (131 OPS+) and this season his slash line was .270/.368/.473 (131 OPS+), so you can see the consistency from season to season. It just gets to a similar point with a series of hot and cold streaks during each season.
It’s unlikely the Cubs will just go back and keep both, but it’s possible they pick one to re-sign while letting the other walk. It’s clear that Suzuki is the better player, but that also means the Cubs will face tougher competition to retain his services.
If the Cubs lose both, the internal options could be Pedro Ramirez (a rookie utilityman who has shown great promise) and Matt Shaw, who has moved from everyday third baseman to utility man this season. Of course, if both players get everyday duties in the corners of the outfield, that really reduces the depth of the infield. Bringing Michael Conforto back to the platoon in a corner of the outfield could help things. Maybe they’ll try to bring back Tyrone Taylor too.
Otherwise, the Cubs are considering taking a deep look at Kevin Alcántara or looking outside the organization for help.
It says here that a wise path would be to bring back Suzuki, put Shaw in left field, and use Ramirez as a backup utilityman. Conforto and/or Taylor would be a bonus. Good leads for Happ, unless his market completely hits the point where he takes a terribly cheap one-year deal to restore value.
2. Can the pitch be repaired?
As noted, the Cubs’ player group position was incredible in 2026. The run prevention numbers weren’t as bad as the pitching, thanks to a defense that papered over much of the pitching issues. But not all. There were a lot of bad things about the pitching staff.
Yes, there were injuries. Promising youngster Cade Horton was lost for the season after just two starts. Ben Brown emerged as a breakout beast and was unable to pitch after June 19th. Matthew Boyd spent time on the IL. Justin Steele has now missed nearly two seasons following Tommy John surgery in early 2025.
There were also failures. Edward Cabrera has been a debacle so far. Jameson Taillon had to be designated for assignment. Boyd and Shota Imanaga were inconsistent, even though they were pretty good. The bullpen also experienced numerous injuries and poor performance.
The Cubs don’t appear to have the pitching system in place, organizationally, to be able to achieve many of their own wins, forcing them to hunt for bargains every offseason.
One thing this front office seems to like to do is take risks on volatile (Cabrera, Phil Maton, Jacob Webb, Ryan Zeferjahn) or injury-prone (Hunter Harvey) pitchers, in hopes of hitting the lottery. Sometimes it works. With the possible reward on high-risk, high-reward moves, there is the downside of injury concerns or older players (Hoby Milner) going cheap.
So, of course, there’s a built-in excuse for the front office when there are tons of injuries up and down the pitching staff. However, some of that comes with the territory, given the approach. That meant a midseason scramble to grab David Peterson and then Kevin Gausman and Clay Holmes before the trade deadline. This is not a model that many organizations would want to follow.
How are things going for next year?
Gausman, Imanaga and Peterson are free agents. Boyd has a $15 million mutual option, which he can probably beat on the open market. The same goes for Holmes and his $12 million player option. This means that a very realistic scenario is that the entire the end-of-season rotation is gone. Backup starter Colin Rea is also a free agent, as is long reliever Aaron Civale.
That means the rotation heading into the offseason likely includes Cabrera, Steele and Javier Assad, with the hope that Horton returns midseason and relies on Brown’s neck injury to heal properly.
The bullpen will also need a lot of work, even if Daniel Palencia is repaired and Zeferjahn polishes his stuff next year. There is a $2.5 million club option for Webb, which the Cubs might as well pick up in hopes that his midseason stretch this year could be what he looks like all season in 2027.
It looks like the Cubs will have a lot to accomplish on the pitching side this offseason.
Another thing to note: catcher Carson Kelly seems to be working really well with the pitching staff and he’s hitting free agency as well.
3. Is it really enough?
This is the overarching question for Cubs ownership. The post-2021 rebuild is complete and the Cubs went from 83 wins in 2024 to 92 wins and one loss in the NLDS in 2025, then fell back in 2026 with 89 wins and one loss in the Wild Card Series.
It was Jed Hoyer’s sixth full year as head of baseball operations and the Cubs neither won the division nor advanced in the NLCS. When Hoyer was second in command behind Theo Epstein, the Cubs underwent a more thorough rebuild and were still in the NLCS in year four of that administration before winning 103 games and the World Series in year five. In Year 6, they won two division titles and three straight trips to the NLCS with this ring.
The Cubs are currently embarrassed by the Brewers. They finished five games behind the Brewers in 2025 and lost to them in the NLDS, and this year finished 14 games behind them. The Brewers won the season series nine games to four, including five of six in September.
Player development leaves a lot to be desired. There have obviously been some wins, but not enough to form the backbone of the ballclub’s future without having to rely heavily on free agency or trades.
It certainly appears to be “good enough” for the Ricketts family, as there are no signs of significant changes in the front office at this point.
But should that be enough? Playing second fiddle to the Brewers while winning about 90 games and getting bounced in the early rounds of the playoffs?
That certainly doesn’t seem to be the case. I’m not saying Hoyer or general manager Carter Hawkins should definitely be fired, but I’m not sure either move should be ruled out. I’m also not necessarily saying the front office needs to spend more.
What I’m saying is that the status quo takes a backseat to the Brewers and that can’t be enough. Something has to improve.
Gn sports
