The Cubs face a crucial offseason in 2024-25. Before it begins, Cubs writers Tony Andracki and Andy Martínez address 5 key areas of the team — and why you should and shouldn’t be optimistic about them. Next up, the path to the playoffs in 2025.

Tony Andracki: Will the Cubs make the playoffs in 2025?

At the end of the day, that’s what it all comes down to. It’s really the main question worth answering. We can discuss position groups or free agents or potential trades, but all roads lead to the same thing — how does it set the Cubs up to make the postseason in 2025?

They haven’t been to the playoffs since the shortened season in 2020. The Cubs haven’t won a playoff game since 2017.

Over the last two offseasons (going into the 2023 and 2024 campaigns), I believed the Cubs were primed to get over that hump and get back into the postseason. It ultimately didn’t work out that way.

So you know what I’m going to do?

The exact same thing. 

Yes, I think the Cubs are set up to potentially be a playoff team in 2025. 

Andy Martínez: Hopefully everyone in life has someone as optimistic in their life as you are Tony! 

The Cubs should have been a playoff team in 2023. They should have made the playoffs in 2024. 

They SHOULD make the playoffs in 2025. 

But there’s a reason the word “should” was emphasized. You’re absolutely right Tony, the rotation could be a strength, the offense could be better, free agency is deep. Blah, blah, blah. 

None of that matters because reaching the pinnacle of the game — October baseball — is the baseline that the Cubs will be judged on in 2025. 

“From the top down this year, the expectation was to play in the playoffs, and we didn’t get there,” Cubs president of baseball operations Jed Hoyer said. “And we have to be better to move beyond 83-79 two consecutive years. We need to be better to get beyond that.”

As it stands, it’s hard to see a path towards the Cubs being a playoff team. Craig Counsell was brought in and the record remained the same. A potential cornerstone first baseman (Michael Busch) and a top-of-the-rotation starter (Shota Imanaga) were acquired — and they finished with the exact number of wins as the year prior. 

[MORE: Hoyer impressed with rookie campaigns of Michael Busch, Shota Imanaga]

The rest of the division will make it interesting in 2025, too. Milwaukee might lose Willy Adames, but will likely return Christian Yelich and Brandon Woodruff from injuries and Jackson Chourio might be the player with the most potential in the division. Plus, they lose players often and seem to find a replacement out of nowhere. 

Cincinnati has a really good roster on paper and now augments it with one of the best managers in Terry Francona. Pittsburgh has an intriguing young core and a rotation with Paul Skenes, Jared Jones and Mitch Keller is nothing to scoff at. St. Louis might be entering a rebuilding phase but Masyn Wynn, Sonny Gray, Nolan Arenado, Willson Contreras and Brendan Donovan are still under contract at the time of writing, meaning you can’t entirely write them off yet. 

Something has to change — and likely will — this offseason for the Cubs. But until then, it’s hard to bank solely on internal improvements to carry them into October. 

There’s a plethora of arguments to make as to why this team will make the playoffs — some have been made in this series — and there’s just as many points as to why they won’t. It’s on Hoyer and his brass to augment those reasons for why they can make it and mitigate the reasons they can’t. 

Until then, it’s hard envisioning seeing this team playing beyond their season finale on September 28 against St. Louis next year. 

TA: Totally agree with all that, Andy. 

The old adage in sports is the ultimate truism: You are what your record says you are.

And the Cubs’ record has clearly indicated they are not a playoff team the last 2 seasons (plus the 2 rebuilding years prior to that). In fact, the Cubs went from missing the postseason by just 1 game in 2023 to 6 games in 2024, so despite the same win total, they’ve actually fallen a bit off the pace compared to the rest of the league.

Why should we think things will change in 2025? 

For one, it sometimes just takes bounces going your way. Look at the rosters in Kansas City or Detroit. Neither of those teams looked like anything close to a playoff roster entering 2024 and even throughout the middle of the season — the Tigers sold at the deadline!

Yes, they were able to beat up on the lowly White Sox in the AL Central and I don’t anticipate any of the NL Central squads to lose 120 games in 2025. 

But the Tigers and Royals are proof that sometimes teams are just a hot streak away from making the postseason. The Cubs very likely would have been in that spot with their second-half hot streak — if it wasn’t for the fact that the teams ahead of them in the standings (Padres, Braves, Mets, Diamondbacks) all performed even better over the final few months of 2024.

But that’s just one path into the playoffs — hope things bounce your way.

The other path is within the Cubs’ control — build a roster that wins more than 83 games.

Again, that’s very simple to say. Obviously difficult to execute.

I thought Hoyer and Co. had built a roster in 2024 capable of winning enough to get into the postseason. It didn’t happen, but that doesn’t mean a blowup is needed – nor is that likely to happen, of course.

Finding a way to enhance the offense would be a huge key — either by extracting more consistency and potential out of the current group or adding a potential star-level bat into the lineup.

Making the bullpen a top priority this winter is another big factor — and one that Hoyer has already said he will attack.

The rotation is already a strength and could get even better if the Cubs make a big splash with a free agent like Corbin Burnes or Max Fried. 

The Cubs defense was surprisingly up-and-down in 2024, but I anticipate it being a strength in 2025 with Gold Glove-caliber defenders all over the diamond.

Couple that all with young talent descending upon the big-league team and there certainly is a lot to like about this roster. The Cubs also have some financial flexibility this offseason, especially if Cody Bellinger opts out and his contract comes off the books.

From a leadership standpoint, I think Year 2 for Counsell will bring about even more comfortability and knowledge of every corner of the organization. That very well could lead to what Counsell was brought in to do – win. 

Let’s see how this offseason plays out but right now, I don’t see any reason to stray from my stance that the Cubs should contend for the playoffs in 2025.

Yin and Yang Series:

How do the Cubs build a top-level bullpen in 2025?
Is the Cubs offense in a good spot?
Will the Cubs rotation remain the strength of this team?
Catching is a top priority for the Cubs this offseason
Are the Cubs set up to be a playoff team in 2025?