Chicago Cubs under immense “must win” pressure in 2025 after busy offseason

The Chicago Cubs have made some major moves this offseason.

From the signing of free agent LHP Matthew Boyd for the starting rotation all the way through the recent trade for former Houston Astros closer Ryan Pressly, the Cubs have done some serious roster building. And the addition of Astros all-star right fielder Kyle Tucker, of course, would be the biggest of all the moves.

“Win Now” Pressure Mounts On Chicago Cubs

But with all the additions and improvements, there also comes significant pressure.

The Cubs will have one year of Tucker and one year of Pressly (not to mention one year of Caleb Thielbar, Jon Berti, and Colin Rea) before they likely disappear in free agency. They’ll have to prove that signing Boyd, rehabbed from Tommy John surgery, was a prudent investment of $29 million over two years. They’ll also have to justify that trading Cody Bellinger in favor of keeping Pete Crow-Armstrong at center was a savvy move and not just a salary dump.

Needless to say, there will be a lot on the Cubs’ front office plate and a lot of direct pressure on president of baseball operations Jed Hoyer, who is also headed into the final year of his contract with Chicago.

The Most On The Line

Will Leitch of MLB.com has recognized the incredible amount of pressure on the Cubs in naming them the team in the NL Central with “the most on the line” headed into the 2025 season.

Per Leitch:

“The good news is that the Cubs traded for one year of Kyle Tucker. The bad news is that they’re guaranteed only one year of Kyle Tucker. The new Cubs right fielder is instantly the best player this roster has featured since its World Series title in 2016, and with him comes heightened expectations right out of the gate.

The Cubs would seem to be the favorites in this division, but they are far from a lock. The frequently overperforming Brewers aren’t going anywhere; the Reds are loaded with young talent and have a new World Series-winning manager in Terry Francona; the Pirates have Paul Skenes and an excellent rotation around him; even the Cardinals, as idle as they’ve been this winter, are coming off a winning season.

If the Cubs don’t win right now with Tucker on the roster — assuming they don’t sign him to an extension before or during the season, something widely seen as unlikely — and go two straight years under manager Craig Counsell missing the postseason…well, what exactly are we doing here? The Cubs haven’t won a postseason game since 2017, something that (quite understandably) perturbs their fans. They now have a superstar on the roster. They better do something with him while they can.”

Losing Means Big Changes

The reality is that the Cubs have done more this offseason than the rest of the teams in their division, combined. They SHOULD win the division.

A harsher reality is that if the Cubs DON’T win the NL Central, we may see some sweeping, fundamental changes in the team, across the board, from coaching to roster approach to front office management.

And for Hoyer, personally, this year could define whether his run as Cubs bossman is seen as a failure or as a success.

That’s the kind of pressure involved when you’re on the record as being “all in” when it comes to making postseason play and when you’ve made the moves to actually be “all in.”

From this point forward, the future of the organization plays out on the field. The Cubs are backed into a corner and must win.