Five Things the Cubs Must Do To Become Contenders in 2025

Few teams have been as confusing in recent years as the Chicago Cubs. After pulling the plug and trading off their World Series core in 2021, the Cubs did not spiral into a traditional rebuild, instead opting to sign veterans and attempt to compete.

The result has been the no man’s land in between good and bad, settling in that grey area. Although they did not bottom out and build back through the draft, the Cubs have managed to construct a good farm system with pieces to be excited about while also adding proven pieces. However, it has not resulted in the playoffs, at least not yet.

Each offseason, the Cubs have continued to add and even invested heavily in Craig Counsell as their manager. With all signs pointing towards more additions, this upcoming winter is a crucial one in Chicago.

If next year is another ho-hum season, talks of a roster shake-up will only become louder. Today I am going to take a stab at identifying a few important decisions the Cubs need to make to return to the postseason in 2025.

1. Cubs Must Bring in a Proven Closer

Although many teams have pivoted from the traditional closer role, it’s typically been out of necessity. Having a proven closer to get the three biggest outs is still a weapon in baseball.

The Cubs have tried a few different arms over the past couple of seasons but lack a pitcher you truly feel comfortable with in the biggest moments.

Adding a closer would push a pitcher like Adbert Alzolay into a more comfortable role outside of the ninth inning. The Cubs have proven they can find lower-leverage bullpen arms and currently have enough options that they can afford to put all of their focus and (bullpen) money toward someone to lock down the ninth inning.

Easier said than done, however. Perhaps the best fit would be Kenley Jansen, who is set to hit free agency. While Jansen has been very productive throughout his career, how much will the Cubs be willing to invest in a 36-year-old?

If Jansen wants term over a one-year deal, you might be rolling the dice, something the Cubs have not been scared to do.

2. Invest in a Veteran Catcher

Since Willson Contreras left, the Cubs have been looking for an answer behind the plate. Miguel Amaya could still be the long-term answer, however, relying on him to shoulder the load while also hoping he provides more offense seems like a big task and unlikely outcome.

Adding a catcher to split time and take some pressure off of Amaya’s plate would give fans much more comfort heading into next season. Of course, catchers who provide plus offense do not just grow on trees.

Do they see if Danny Jansen can find his form? Or, see if their prospects can pry away a catcher from another team? Maybe one of the top needs will be the hardest to address.

I keep coming back to the moves the Cubs made in the past and think if there’s one they regret it would be moving on from Contreras. Especially knowing that a full rebuild was not the plan. Hindsight is 20/20 of course, but I still think they should have stuck with Contreras.

3. Strengthen Infield Depth

The Cubs’ infield, for the most part, is likely set for 2025: Michael Busch at first, Nico Hoerner at second, Dansby Swanson at short, and Isaac Paredes at third. All are MLB-caliber starters, but all come with some questions.

Swanson has had back-to-back down years at the plate, while Hoerner also had a down year in 2024. You won’t find many better defensive combinations, so we can stick with those two and have reasonable hope for a rebound.

Busch has shown enough at first this year, but Paredes has dropped off in a big way since joining the Cubs, slashing .210/.317/.299. Adding some insurance, for injury or poor performance, is important.

No offense to Miles Mastrobuoni, but you can’t bring him back in 2025. How much trust do you have in Luis Vazquez? Top prospect Matt Shaw might factor into the equation, but counting on a rookie cannot be plan A.

The Cubs are an attractive enough destination to draw interest from a higher-end utility infielder. A complete makeover of the backup options should be in store

4. Cubs Should Move on From the Roster Roaches

For the most part, the Cubs have had a full roster turnover over the past three seasons. I’ll give them credit, they have moved on from some important players to the organization and started fresh. Now, it is time to move on from one last established player and make one overdue move.

The move that has needed to happen is moving on from Patrick Wisdom. The high-strikeout, power-only bat has run his course in Chicago.

While the Cubs tried to make Wisdom into more of a utility player, I think we have all seen enough of his pinch-hit strikeouts. His usage has gone down and so has his power. Chicago can afford to spend on a higher-end utility option that has more to offer and provides a more refined skill set.

Kyle Hendricks was an important part of many Cubs teams and generally underrated by the common baseball fan. The crafty starter had said that he plans to pitch in 2025, but that needs to be in a different jersey.

His contact is up and a clean break is in order. With the way the rotation is currently constructed, the Cubs can move on and use that money toward a back-end arm that offers a bit more than Hendricks.

5. Add a Back-End Starter

Chicago’s rotation of Justin Steele, Shota Imanaga, Jameson Taillon, and Javier Assad is a very strong foundation. Adding another starter would be a luxury, especially with the talented young arms already in the system on the 40-man roster. But, as the saying goes, you cannot have enough pitchers.

The Cubs have money to spend, and with the number of injuries we see year in and year out to starting pitchers, adding a veteran to round out the rotation could only be a plus.

Doing so might also allow for the Cubs to become more comfortable trading away a young arm to improve the team elsewhere. It would also give them some flexibility with Ben Brown coming off injury as they try to manage his innings.

Conclusion

The more I look at it, the more I think the Cubs are stuck, for lack of a better term. Most of their roster is set heading into 2025, which might not be the best thing considering they could easily finish 10 games back of first place.

Like I mentioned earlier, a roster shake up is probably a year away, so they have what they have.

Improving on the edges, getting better depth, and banking on improvement from a few younger players, especially Pete Crow-Armstrong, might be the best course of action. Even if it’s not, it looks like the most likely path.

Maybe the Brewers just have a certain magic and the other NL Central teams are just too far behind. Time will tell.