Franchise management throwing guaranteed wins away like the characters do

[GhostEmperorX]

So basically, I'm sure we're all familiar with how, for different reasons, a few notable protagonist characters (or deuteragonist depending on the point in time) go out of their way to reject the easiest paths to victory when they're on top, whether that's pride, carelessness, or w/e else.
It's practically a franchise staple with how frequently it's happened.

As one looks deeper into what has happened with the core management side of things over the years (particularly Toei, Bandai, Shueisha, and other involved rights holders), it is found to be true of these companies as well. What instances of this come to mind for you?

Personally, I've been thinking, and the story of Funimation's origin and subsequent rise (along with the brand dissolution into CR) really played out almost exactly like the circumstances that led to Cell becoming perfect (from 2nd form onwards).

Another instance would be Yamamoto (who I'm just finding out practically told on himself in an OST release), as well as certain elements of the original run, but curious to hear what everyone else thinks.