To be clear, I'm not over the moon with Hoyer. I'm mostly willing to give him a pass on 2021-2023; he was essentially forced to gut the team mid-2021 due to "biblical losses" and the team in 2023 probably over performed what it looked like it'd have done. Rebuilding the roster is something I'll give you two years to get right. You can see that differently, but that's my viewpoint.
Entering 2024, I felt the Cubs were a player short in the offseason, they missed the boat at the deadline, and deservedly, crashed on the back end. It was a team that had some negative variance but the Cubs didn't properly handle that. That's on Jed, don't disagree.
2025, the Cubs landed on their high end of projections. It's an imperfect roster; they missed on Scott and Bregman, ended a player short on the offseason and then couldn't get another useful piece at the deadline. Even if we're assuming SP prices were out of control, relievers were doable and two of the three players the Cubs acquired weren't useful in the playoffs. They also brought in players who did better than we expected - they get credit for that. Overall, it was a successful, yet flawed year in the sense that I don't think the Cubs optimized their output.
When it comes to spending, the spending does give the Cubs a boost, but they've also been highly dependent on outside help as the farm system wasn't really producing much. I can't find many places where the Cubs are overspending right now; they're pretty much market value or surplus value on their contracts, too. So I think it's a bit overblown, but it certainly gives the Cubs an advantage and it's fine to point that out, too.
We'll see what 2026 brings. At this point, when it comes to Jed I expect a few things:
The Cubs will do well with player acquisition and they won't really miss
The Cubs will likely not get the top-wishlisted player ever
The Cubs will routinely be a player short
The Cubs will be a pretty good and competitive roster
Fans will be upset initially at many of the signings but later will turn out fine
I'd like to be proven wrong at some point by their inability to get "the" guy they want or to close out a full-offseason or deadline without being a perceived player short.