Cubs Looking for More a Year After Ending Playoff Drought

Entering the 2025 season, the Chicago Cubs were a few years removed from their most recent postseason appearance.

Prior to that, they’d made the 2020 MLB playoffs as a National League Wild Card team following the 60-game regular season. Their last postseason bid in a full season was in 2018. In both years, though, they didn’t win a game.

That meant the Cubs had gone seven straight seasons with zero playoff wins.

Despite that, the expectations entering last year were obviously high. They had a mix of established veterans and young talent. They acquired Kyle Tucker via trade as their big offseason splash. There were real expectations on that team to get back to the postseason.

And that’s what they did. Though it wasn’t always pretty, Chicago put together a 92-win season. That wasn’t enough to secure the NL Central crown, but it was enough to earn them a Wild Card spot.

Their run to Game 5 of the NL Division Series ended in disappointing fashion, when they ultimately lost the series to the Milwaukee Brewers, but the Cubs brought playoff baseball back to Wrigley Field. The energy around the ballpark at that time made everyone remember how important that is.

Now, they’re looking for more.

Though Tucker has moved on to the Los Angeles Dodgers, Chicago has filled in the roster behind him with potentially huge contributors.

Back in January, the Cubs signed Alex Bregman — who they’d pursued last offseason — to a five-year, $175 million deal. He’ll take over at third base, where he’s previously won a Gold Glove (2024) and a Silver Slugger (2019) and earned three All-Star nods (2018-19, ‘25).

His ability on both sides of the plate already represents a huge addition, but his leadership qualities and presence in the clubhouse will be a big factor, too.

A few days before signing Bregman, Chicago acquired Edward Cabrera from the Miami Marlins. He’s not quite a finished product and has some injury concerns, but his potential is tantalizing. If he can put it together while with the Cubs (they also hold multiple years of club control of Cabrera), he can become the top-of-the-rotation arm they’ve been looking for.

Their other additions came in the bullpen or on the bench. Phil Maton, Hoby Milner, Hunter Harvey and Jacob Webb are new faces in the relief corps. Dylan Carlson (officially selected Tuesday) and Michael Conforto and Scott Kingery (both officially selected Wednesday) have plenty of big league experience between them to add to the bench.

Some additions shore up the roster, some are expected to be key contributors. If the Cubs get where they want to go, all will play a role in it.

But, with so much of last season’s roster returning, it’ll most likely come down to what kind of seasons those players are able to put together. On the position player side, questions include:

• Pete Crow-Armstrong just reportedly signed a six-year, $115 million extension starting in 2027. Can he build off a breakout 2025 and put together a complete 2026?

• Seiya Suzuki (starting the season on the 10-day IL) and Ian Happ are in the last years of their deals. How will the Cubs’ top corner outfielders perform in contract years?

• Nico Hoerner and Dansby Swanson should continue to be among the top up-the-middle duos in baseball. How productive will they be on the offensive end?

• Can Michael Busch produce offensively at the level he did last season, particularly with more opportunities versus lefties? Will Matt Shaw make a smooth transition into a utility role? How will Moisés Ballesteros fare with a bigger role? Will the catching tandem of Carson Kelly and Miguel Amaya perform overall like they did last season?

And on the pitching side:

• Cade Horton excelled in his first taste of big league action last year. How does he follow that up in 2026?

• In previous years, both Craig Counsell and David Ross were hesitant to name a closer entering the season. Counsell, though, confirmed to reporters early in spring training that Daniel Palencia is the team’s closer to start the year.
  
  After an eye-opening 2025 and a dominant World Baseball Classic, can Palencia carry that through the regular season? And at that rate, will the Cubs even be looking for a closer at the trade deadline?

• Justin Steele was placed on the 60-day IL on Wednesday but could return as early as late May. But how will he look after another major elbow surgery?

• Will Matthew Boyd pitch like an All-Star for the second year in a row? Will Shota Imanaga get closer to his 2024 form? Will Jameson Taillon perform like a consistent veteran? Will the returning bullpen arms like Colin Rea and Caleb Thielbar be as consistent as they were last season?

Clearly, there are some questions about the roster, but coming off a much-needed postseason appearance, there’s reason to be confident in this Cubs team. There’s reason to expect more than a run to a winner-takes-all game in the NLDS.

And that isn’t limited to the fanbase. The people in charge in Chicago have said the same.

Said chairman Tom Ricketts to reporters early in spring training: “Everyone had high expectations last year, and I think they’re higher this year. I mean, obviously, we have effectively the same team as last year, plus a couple key components that should contribute. So, I would expect everyone to have higher expectations this year.”

Said president of baseball operations Jed Hoyer to The Athletic’s Jon Greenberg: “[Expectations] are high…I do feel like our group got a taste of what it’s like in the playoffs, what Wrigley’s like in a playoffs, and I sense a really hungry group this year, a really serious hungry group.”

The players certainly have those high expectations for themselves, too. And with a very strong group in place, an even deeper run into October is certainly in the cards.

But that is still months away. The marathon to get there finally begins at 1:20 p.m. today at Wrigley Field.