The Chicago Cubs front office, this past offseason, declared themselves to be “all in” when it came to making a serious playoff run in 2025.
Whether or not they were truly “all in,” however, can be debated. They never made a play at any high-end starting pitchers. They made only a token effort at grabbing Alex Bregman. They were outbid by the Dodgers for closer Tanner Scott.
What can’t be debated, though, is that they were successful in putting together a really quality, versatile team that has thus far proven itself to be as resilient as it is talented.
Jed Hoyer’s Push To Win Now
Cubs president of baseball operations Jed Hoyer deserves a good portion of the credit for this 2025 team, but some will insist that Hoyer’s contract status pushed him into a sense of “win now” urgency. With his deal set to expire at the end of this season, the exec’s back was against the wall and he had to produce his first postseason team since taking the Cubs helm from Theo Epstein in 2021.
The 3-for-1 Kyle Tucker trade with the Houston Astros, specifically, is pointed to as the kind of bold move forced into reality by the pressure to win now or else. In the deal, the Cubs traded away Isaac Paredes, Heyden Wesneski, and no. 1 draft pick Cam Smith for a multi-tool star in his contract year who could very well be gone next season. That’s a mighty big “win now” gamble and not in the Cubs front office character profile at all.
Contract Extension Imminent?
MLB insider and ESPN analyst Jesse Rogers feels that Hoyer’s gamble will pay off and that Cubs ownership will not only extend him, but will offer him his new contract sooner rather than later.
Per Rogers on ESPN Chicago’s Waddle and Silvy Show:
“I would not be surprised if he’s given a new contract by the all-star break. I think he’s more likely to get it sooner rather than later, possibly before the trade deadline. It’s like kind of one of those things, if you’re gonna impact our team for years to come, let’s sign you up. I really could see that. Now, the other option is three days after the season ends. But I think he’s in line for that extension– three years, five years, whatever [Tom] Ricketts wants to do. But I would not be surprised if it happens between now and July 31st.”
For the record, Hoyer as said repeatedly that the decisions made this year have nothing to do with his contract status.
“It’s not going to change any decisions we make,” Hoyer told the Chicago Sun-Times back in January, one month after acquiring Tucker. “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.”
How This Impacts The Chicago Cubs
Whatever the case, Hoyer’s contract status may, indeed, affect how things go down as the Cubs close in on the July 31st trade deadline.
Will an extended Hoyer, with a vested interest in preserving the team’s future, be less likely to part with prized prospects in pursuit of a major deadline acquisition?
Could the opposite be the case? Could a secure Hoyer push harder to make the big deals needed to get the team a deep playoff run (or more)?
As is always the case, time will tell.
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