Chicago Cubs 'Under Heavy Pressure' in Season Where They 'Have To Win'

The Chicago Cubs need to start showing some results on the field or major changes could be on the horizon.

Sep 22, 2024; Chicago, Illinois, USA; Chicago Cubs pitcher Ethan Roberts (39) and manager Craig Counsell (30) argue a call against the Washington Nationals during the eighth inning at Wrigley Field. | David Banks-Imagn Images

Outside of the 2020 season which was impacted by the COVID-19 pandemic, the Chicago Cubs have not made the playoffs since 2018.

They haven’t been overly competitive in that duration either, finishing double-digit games behind first place in the National League Central three times in five years and never finishing fewer than seven games back of the top spot.

Likely not a coincidence, this drought began when Theo Epstein left the front office, as this is the fifth campaign they are preparing for without him as an executive.

The Cubs have a strong brain trust in place with Jed Hoyer leading the front office and Craig Counsell as manager, but for whatever reason, things haven’t quite clicked on the field, which is part of the reason why Chicago is under so much pressure entering the 2025 campaign.

Over at The Athletic, Jayson Stark put together a survey with 32 MLB insiders, including current and former executives, coaches and scouts. They were asked a series of questions, one of which was which team/front office/coach was under the most pressure.

Running away in first place with an astounding 22 votes was the Toronto Blue Jays.

In second place was the Cubs, who garnered 12 votes.

“The Cubs have to win,” one voter bluntly put it.

As the most aggressive team looking for upgrades this offseason in the NL Central, Chicago is in a great position to make its way back to the postseason.

Acquiring Kyle Tucker from the Houston Astros was a huge addition to the middle of their lineup.

Depth pieces were added in catcher Carson Kelly, starting pitchers Matthew Boyd and Colin Rea and the bullpen got a much-needed boost with Ryan Pressly being acquired in a separate trade from Tucker with the Astros.

With a strong core already in place and even more help on the way with a stellar farm system, the Cubs are set to succeed, not only in 2025, but the foreseeable future.

Alas, with those kind of roster upgrades, comes expectations to perform.

“The Cubs,” said one rival exec, “feel like they’re under heavy pressure.”

The Milwaukee Brewers, who finished 10 games ahead of Chicago to win the division in 2024, took some steps back with their roster this winter. The same can be said for the St. Louis Cardinals. The Cincinnati Reds should be improved with Terry Francona as manager, but the Cubs, on paper, look stronger. Chicago should thank Pittsburgh Pirates ownership for not wanting to spend, as their pitching staff is contender-worthy.

Because of that, things are certainly lining up well for the Cubs.

But if they underperform, major changes could be on the horizon.