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May 3, 2025; Milwaukee, Wisconsin, USA; Chicago Cubs left fielder Ian Happ (8), center fielder Pete Crow-Armstrong (4) and right fielder Kyle Tucker (30) celebrate after beating the Milwaukee Brewers at American Family Field. Mandatory Credit: Benny Sieu-Imagn Images

The Chicago Cubs Cling To NL Wild Card Lead With 25 Games To Prove Themselves

Originally posted on Stadium Rant | By Brandon Gordon | Last updated Sep 1, 2025 1:09 PM ET

The calendar has flipped to September, and the Chicago Cubs have just 25 games left to prove they deserve to play October baseball. Sitting atop the NL Wild Card race, the Cubs are in solid postseason position but still trail the surging Milwaukee Brewers by 6.5 games in the NL Central. Overtaking Milwaukee looks unlikely, but as Chicago fans know all too well, stranger things have happened in September. The Cubs’ recent moves are setting up for an eventual postseason push.

Roster Reinforcements Arrive

On Sunday, August 31, the Cubs made a pair of notable additions. Cleveland Guardians veteran switch-hitter Carlos Santana joined the team, providing a versatile bench bat and postseason experience. Meanwhile, right-hander Aaron Civale was claimed off waivers from the crosstown rival Chicago White Sox and will pitch out of the bullpen in a bulk-relief role.

More help is on the way. Jameson Taillon and trade-deadline acquisition Mike Soroka are expected back within the next couple of weeks. The club also made an eyebrow-raising move by swapping top outfield prospects, calling up Kevin Alcantara while sending Owen Caissie down. With Ian Happ, Pete Crow-Armstrong, Kyle Tucker, and Seiya Suzuki entrenched in the outfield, it’s unclear how Alcantara fits in—but sometimes a fresh look provides the spark a team needs.

Pitching Staff Gets Deeper

The current rotation of Shota Imanaga, All-Star Matthew Boyd, rookie Cade Horton, Colin Rea, and Javier Assad has held its own, but reinforcements could be the difference come October. When Taillon and Soroka return, either Rea or Assad could transition into a long-relief role, while the other could be used as a sixth starter. Civale adds another multi-inning option and could make a spot start if it were necessary. Suddenly, manager Craig Counsell has the makings of a flexible, playoff-ready pitching staff.

Offense Must Reignite

The bigger question is at the plate. Since the All-Star break, the Cubs are just 21–20, unable to find the offensive rhythm that carried them early in the season. For this lineup to click, they’ll need much more consistency from Kyle Tucker, Ian Happ, Pete Crow-Armstrong, and Seiya Suzuki. That core four drives the offense, and when they’re hot, the rest of the order feeds off them.

Santana’s switch-hitting presence pairs with deadline pickup Willie Castro to give the Cubs flexibility off their bench. The possible return of catcher Miguel Amaya before the postseason could further strengthen depth. Will Owen Caissie and Moises Ballesteros be called up once rosters expand? Don’t be surprised if veterans Justin Turner and Reese McGuire find themselves on the outside looking in when it comes to the October roster.

End Of My Chicago Cubs Rant

Ultimately, this stretch run comes down to whether Craig Counsell can push the right buttons. The Cubs have been inconsistent since the break, struggling to get both pitching and hitting firing on all cylinders. With 25 games left, however, they’re far from finished. The NL Central may be slipping away, but a Wild Card berth is theirs to lose. If the reinforcements pay off and the bats wake up, the Cubs could enter October not just as participants, but as a team nobody wants to face.

One thing is certain: the next 25 games will define whether this Cubs team is simply good or great enough to play meaningful baseball deep into the fall.

From one Cubs fan to another: Keep Calm, and Fly the W

This article first appeared on Stadium Rant and was syndicated with permission.

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