Four months into the 2025 MLB season, the Chicago Cubs have had a year to remember. At 62-43, Chicago is not only tied for first place in the NL Central, but also for the best record in the National League. Sure, there are areas where they can improve at the deadline, but they look like a team capable of winning the World Series. With that in mind, it comes as little surprise that the team has reportedly extended Jed Hoyer's contract, according to Jon Heyman of the New York Post.
Cubs baseball president Jed Hoyer and the team agree on multi year extension
— Jon Heyman (@JonHeyman) July 28, 2025
Hoyer certainly appears to be deserving of this extension. The Cubs have built a great team set up well now and long-term. But the timing of the extension is a bit odd: I mean, the trade deadline is in three days, and the postseason is in just a couple of months. I get why Hoyer would want security, but shouldn't the Cubs want to give this a bit more time before committing?
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Cubs could come to regret Jed Hoyer extension in record time
Again, Hoyer deserves it right now, but things can change awfully quickly. The trade deadline, as mentioned above, is in less than 72 hours. What if Hoyer's moves (or lack thereof) backfire? I mean, the Cubs could really use another high-end starter; what if Hoyer doesn't get one? What if the starter Hoyer acquires fails to meet expectations? What if whatever Hoyer decides to do at third base, whether that's keeping Matt Shaw or acquiring someone else, backfires?
The Cubs are entering the trade deadline hoping to win the World Series. What if they can't make it out of the Wild Card round as a result of Hoyer's deadline activity?
We can even look at the worst-case scenario. The Cubs are where they are largely because Hoyer acquired Kyle Tucker in a deal with the Houston Astros over the offseason. Tucker has been as advertised, if not better, but the reason the Cubs were able to get him in the first place is that he was a rental. What if the Cubs don't win the World Series this season and then watch him leave in free agency soon after? Then, the Cubs will have traded multiple years of Cam Smith, Isaac Paredes and Hayden Wesneski for just one year of Tucker without a ring. That will not look good on Hoyer's resume.
I'm not saying these things will happen, and I do believe Hoyer has earned Chicago's trust, but the timing is weird. If the Cubs were willing to wait this long to give him an extension, why not just wait until later to see how the rest of the season unfolds? The Cubs were probably wise to ensure Hoyer sticks around long-term, but this could also backfire quicker than anyone anticipated.