When Cubs manager Craig Counsell addressed his team after Game 5 of the National League Division series, he assured them that despite the postseason exit, they had done a lot to honor the city written across their chests.
“Obviously everyone’s happy to put on the Chicago uniform,” reliever Brad Keller said Saturday night, standing in front of his locker in the visitors clubhouse at American Family Field. “It’s tough. We had a really good group. We had a lot of veteran guys. I felt like we bounced back through some tough times, through some slumps, through some good times.
“We were pretty even-keel all throughout the season. Even when the moments got big in the playoffs, I felt like we still rose to the occasion.”
It was true. The Cubs had won three elimination games, first to beat the Padres in the wild-card round, and then to even the NLDS after falling behind 0-2 in the series to the Brewers. But that was where their 2025 story ended.
Because the Cubs had scraped and clawed back from the edge, the fall felt all the more sudden. They had believed, regardless of the odds, that they would bounce back. And in the process, they’d made onlookers believe, too.
Then it was over.
“That’s a harsh reality,” shortstop Dansby Swanson said Saturday. “Sports in general can do that. There’s only one team at the end of the year that gets to celebrate. Everyone else feels the same kind of pain. So, I felt this before, and doesn’t get more enjoyable. It honestly probably hurts even more the more you do it.”
Swanson was surrounded by a mass of reporters and TV cameras. A huge media contingent had driven up to Milwaukee from Chicago to cover a possible series-clinching game.
The next question tried to put a positive spin on the pain. Was there a way to build off it?
“When emotions are going, there’s not really a good answer for that right now,” Swanson said.
While the players were channeling all their energy and focus into their performance on the field, however, the front office was juggling both the present and the future.
Baseball operations departments that don’t start planning for the offseason during the playoffs risk falling behind. And president of baseball operations Jed Hoyer has reiterated year after year that sustained success was the goal of the last rebuild.
This trip to the postseason can’t be a one-off.
“That’s the expectation of the organization, the expectation of the players, is to get back in the playoffs,” left fielder Ian Happ said. “It’s really hard. It’s really hard to get here. It’s really hard to win playoff series against good teams. And so the fact that we expect to be here doesn’t make it hurt any less when you’re here and you don’t get it done.”
Now, the players turn it over to Hoyer and his department.
Every year, the front office has to reimagine the bullpen and bench to some extent.
While injuries hobbled an otherwise pretty steady rotation, it’s the front office’s job to anticipate adversity in a season. It was clear as early as last offseason that the Cubs didn’t have enough starting pitching depth to weather those kinds of blows going into the playoffs.
The Cubs also have a decision to make on a unique mechanism in left-hander Shota Imanaga’s contract. Going into last season, he signed a four-year deal worth $53 million that includes an option for the Cubs to extend his contract to a total of five years and $80 million either this offseason or next. If they never pick up the option, he can opt out.
From the position player group, right fielder Kyle Tucker is the big name set to enter free agency.
The Cubs could go the cost-saving route of relying on a combination of Seiya Suzuki and young talent — including Moises Ballesteros, Owen Caissie and Kevin Alcántara — to fill right field and designated hitter.
If they don’t bring in offensive reinforcements, however, they’ll be placing a lot of faith in internal improvement and development at the major-league level.
The Cubs also have to keep in mind the number of core players whose contracts are up after the 2026 season, and lay out a plan to eventually retain or replace them. Suzuki, Happ, second baseman Nico Hoerner and right-hander Jameson Taillon are all lined up to hit free agency at the same time.
While winning 92 games in the regular season and ending a four-year playoff drought were accomplishments this year, in the battle for the NL Central, the Cubs can’t count on the Brewers to fade. Even after losing impact players in each of the last two offseasons, Milwaukee somehow has also continued to improve.
“I think the standard’s changed around here,” said Taillon, who spoke plainly last year about wanting to do just that. “Something I’m super encouraged about, in that same breath, is the young talent we saw come up this year makes me believe that we can do it going forward. So, I think the Cubbies are here to stay.
“And obviously, so are the Brewers.”
