If Cubs need to sell at trade deadline, Tom Ricketts is faced with Jed Hoyer decision

There's an uncomfortable conversation loading for the Chicago Cubs. Short of two ten-game winning streaks, the 2026 season has been massive disappointment. There's no doubt that injuries are a part of that disappointment, but the three big swings Jed Hoyer took during the offseason have been a massive failure.

Alex Bregman's struggles aren't the primary reason why the Cubs are where they are at this point of the season, but the idea that regression is settling in during the first year of a five-year deal worth $175 million doesn't look good for Hoyer. The multi-year deal for Phil Maton also hasn't aged well, considering the 33 year-old relief pitcher is carrying an ERA of 7.08 on the season. Edward Cabrera also doesn't look like the ace the Cubs mapped him out to be when they sent Owen Caissie to the Miami Marlins.

Beyond the injuries, the collective whiffs that Hoyer seemingly had last offseason is the reason why the door has been cracked open to the team selling at the MLB trade deadline. Now, the Cubs are still firmly in the wild card conversation, but if they don't start winning games soon, even that will be reach by the time July rolls around.

Jed Hoyer remains the Cubs' biggest problem

If the situation dictates the Cubs sell at the deadline, Tom Ricketts will once again be faced with a problem he thought was resolved. Had the Cubs not reached the playoffs in 2025, there was speculation that Hoyer's time with the organization might have been coming to an end. Ricketts didn't wait until the offseason to make a decision, signing Hoyer to a contract extension just days before the deadline last summer.

The moves Hoyer has made sense then would suggest that Ricketts acted prematurely. That's not even mentioning Hoyer's other notable swing, signing Dansby Swanson, is also becoming a burden for the team moving forward.

It's unfathoble to think that Hoyer would be allowed to put the Cubs through another rebuild. No, there likely isn't a scenario where the Cubs completely tear down their roster as Hoyer did in 2021, but it's clear that the philosophy the front office isn't working. Hoyer is the leading voice for that problem.

That puts Ricketts in an uneasy situation. The obvious decision would be to move on from Hoyer, but a year after extending him, the Cubs chairman may not be ready for that mea culpa.

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