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Chicago Cubs front office facing “win or get fired” pressure, says former exec

Posted on April 24, 2025

The Chicago Cubs are showcasing a sense of urgency that has never really been seen before.

That urgency was partly revealed with the 3-for-1 acquisition of right fielder Kyle Tucker from the Houston Astros in the offseason. It became further evident with how quickly top prospect Matt Shaw got demoted to Triple-A, after just 20 games and 68 plate appearances.

With that Shaw move, specifically, it was made clear that the Cubs front office is putting immediate production over development in their run to make something big happen right now.

The reason for the urgency can be traced directly to the job security of the Cubs front office, according to former Cincinnati Reds and Washington Nationals general manager Jim Bowden.

“Win Or Get Fired”

MLB: San Diego Padres at Chicago Cubs Jed Hoyer

In a recent appearance on the Foul Territory podcast, the former MLB executive and current media insider talked about the Cubs’ moves revealing the motivations of those making the moves.

“It’s win or get fired. Jed Hoyer knows that, right?,” Bowden said. “That’s why they made the Tucker deal. You don’t make the Kyle Tucker trade if you think you are gonna be there long-term

“You do not give up six years of Cam Smith for what appears to be one year of Kyle Tucker. So you have to do everything you can to win right now. And again, I don’t think you send Matt Shaw down if you don’t feel that sense of urgency from the ownership.”

Hoyer, Chicago’s president of baseball operations, is in the last year of his contract with the team and it’s been widely opined that his busier-than-usual offseason is directly tied to the push to keep his high-profile position.

The Cubs exec has been with the organization for fourteen years and played a pivotal role in helping Theo Epstein assemble the drought-breaking 2016 World Series team.

Since he took the organization’s top spot in 2021, however, the team has failed to make postseason play, despite aggressive moves to rebuild the farm system with a number of major trades throughout his tenure.

Chicago Cubs President Denies Self-Interest

Chicago Cubs president of baseball operations Jed Hoyer speaks before introducing Craig Counsell

Hoyer has insisted that the moves he’s made have not been driven in any way by his own contract status.

“It’s not going to change any decisions we make,” Hoyer told the Chicago Sun-Times back in January. “That’s what people always ask. ‘You’re in the last year, are you guys going to do things differently?’ It’s like, of course not. That’s not my job.

“This is about the fans. This is about Chicago. This is about the Cubs. These things are so much bigger than me. I’m not going to make decisions that impact a city or a fan base based on my self interest.”

The Pressure Is Real

Chicago Cubs Kyle Tucker

For what it’s worth, Bowden, who picked the Cubs to win the NL Central Division, believes that Hoyer and the front office will stay with the team, despite any pressure put on them to win now and possible pressure down the line, especially when it comes to extending Tucker.

“I think they are gonna be able to keep their jobs,” Bowden added. “But I do think when you see moves like they are making this quickly out of the gate, when they don’t need to, I think it tells you the sense of urgency as the Tucker deal did.

“I also think it is extremely important this front office does everything they can to try to sign Kyle Tucker as soon as possible and not let him get to free agency because if you let him get to free agency and lose him after trading Cam Smith to get him, you know, that’s one of those deals you’ll regret the rest of your career.”

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