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Chicago Cubs: Pressure will really mount in make-or-break June
Imagn Images

The Chicago Cubs started the month of June with a much-needed day off. May was a rough one for the North Siders as they rode a roller coaster of emotions, zooming high at the beginning of the month and then plummeting into some bad, ugly days the rest of the way.

As things stand right now, though, the Cubs wouldn’t even make the playoffs if the season ended today. Their first place spot in the NL Central Division is a significantly less prestigious tie for third place.

But now, unfortunately, the pressure will really amplify as June tends to be one of those months that helps set a team’s realistic expectations for the rest of the season. In the Cubs’ case, there were high expectations in the offseason, with even some World Series chatter being tossed about.

Lots of issues heading into June


Chicago Cubs showcase this stellar mindset in Wild Card Series win 3 Sep 30, 2025; Chicago, Illinois, USA; Chicago Cubs infielder Dansby Swanson (7) celebrates with teammates in the dugout after scoring on a sacrifice fly in the eighth inning against the San Diego Padres during game one of the Wildcard round for the 2025 MLB playoffs at Wrigley Field. Mandatory Credit: David Banks-Imagn Images

Chicago, frankly, has a lot of work to do before anyone revisits the lofty possibilities they once held.

The starting rotation, for example, is an absolute mess and it’s going to need much more than some simple tweaking to get it right.

As noted by Tony Andracki of Bleacher Nation, the Cubs’ starting rotation ranked 28th in the majors with a combined 5.33 ERA—and that’s even including Ben Brown’s outstanding 1.86 ERA run.

Matthew Boyd and Edward Cabrera will be back in the rotation shortly and that can only help. But there’s not much other help on the horizon. Jameson Taillon has been banged around all year and would’ve probably been shelved on any other team with serious postseason aspirations. The Cubs, however, simply didn’t have any suitable replacements for the veteran. Shota Imanaga, meanwhile, has fallen deeply into the dumpster after an excellent start to the season. Colin Rea has been subpar, Jordan Wicks was a disaster, and Javier Assad is still in Iowa. Also, Justin Steele won’t play the role of cavalry to save Chicago’s starting pitching as his setback in recovery from elbow surgery seems more serious than previously implied by the team.

The offense is also struggling, with several high-profile players delivering inconsistent or just flat-out weak production. With a couple of exceptions, everyone struggled at the plate in May—Dansby Swanson, with his .183 batting average on the season, is almost to the point of having to be benched for lack of offense

And just like in the case of the starting pitching, there’s no cavalry riding in to save the day for the offense. The struggling Cubs will have to turn things around on their own.

Mounting pressure


May 29, 2026; St. Louis, Missouri, USA; Chicago Cubs center fielder Pete Crow-Armstrong (4) walks to the on deck circle during the eighth inning against the St. Louis Cardinals at Busch Stadium. Mandatory Credit: Jeff Curry-Imagn Images

Zachary Rotman of Fansided, to back up this mounting-pressure reality, recently named the Cubs as one of the three teams feeling the most pressure headed into June:

“It looked as if the Chicago Cubs were sitting pretty when they won each of their first eight games in May, part of a 10-game winning streak overall. That run brought their record to 27-12, good for first place in the NL Central. But they ended the month with a 32-28 record, meaning they went 5-16 the rest of the way. The Cubs haven’t won a single series since they swept the Reds on May 7.

Chicago isn’t in a bad spot — they’re still four games over .500 — but the pressure is on them to turn it around because of how poorly they’re playing right now. I mean, the Cubs went from a team that was 15 games over .500 to one that’s now in fourth place in the NL Central and would miss the playoffs if the season ended today. That’d be an unacceptable result.

With a light schedule to begin June, the Cubs have a golden opportunity to claw their way back into the NL Central race, even with an unfortunate injury situation. Here’s hoping they don’t blow it.”

The Cubs aren’t “out of it” by a long shot. But June will definitely determine how serious their run for the rest of the season will be.

This article first appeared on ChiCitySports and was syndicated with permission.

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