Former MLB Executive Believes Chicago Cubs Brass in ‘Win or Get Fired’ Scenario

There are a lot of people within the Chicago Cubs organization who are under immense pressure during the 2025 MLB regular season.

Likely atop that list are the president of baseball operations, Jed Hoyer and general manager Carter Hawkins.

Both gentlemen are in the final year of their contracts, operating as lame ducks in their respective positions. Ownership is likely waiting to see how the team turns out before committing to either of them long-term.

In the opinion of Jim Bowden of The Athletic (title, it is playoffs or bust for the team’s brass.

“It is win or get fired for the Cubs front office,” the former MLB executive said during a recent appearance on Foul Territory.

"You don't make the Kyle Tucker trade if you think you're going to be there long-term."

It's win or get fired for Jed Hoyer and the Cubs front office, says @JimBowdenGM. 👀 pic.twitter.com/lIeKHNPuwp
— Foul Territory (@FoulTerritoryTV) April 17, 2025

In most regards, it is so far, so good.

The team is 12-9 and in first place in the National League Central.

But, holding onto that position will be easier said than done, given some of the obstacles the team is already dealing with to overcome.

The starting pitching staff, which was thin on depth coming into the season, is being tested. Javier Assad has yet to pitch this year and Justin Steele landed on the injured list recently, having to undergo surgery on his elbow.

How the Cubs address that loss will have a major impact on the direction the team heads in the remainder of the year.

Expect them to pursue an upgrade on the trade market. They have the means to build a very strong trade package with a loaded farm system that a rebuilding team would love to add a few pieces out of.

With the pressure on to make the postseason, expect Hoyer and Hawkins to aggressively seek out deals that will upgrade the team; they have nothing to lose knowing that their jobs are on the line.

It is part of the reasons why Bowden believes that the Kyle Tucker blockbuster trade was made in the first place.

Hoyer and Hawkins needed an offensive anchor for their lineup. Tucker is incredibly talented and doing exactly what the team had hoped he would, but the price to acquire him was steep.

Third baseman Isaac Paredes, pitcher Hayden Wesneski and star prospect Cam Smith were all sent to the Houston Astros.

Without having Tucker locked into a long-term deal, that is an incredibly risky deal to make, especially when including a young player of the caliber of Smith, who was a first-round pick in the 2024 MLB Draft.

It could also explain why top prospect Matt Shaw was demoted to Triple-A only 20 games into the season.

The pressure is on the Cubs to win now, and the front office is certainly operating in a fashion in which they fully understand that.

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