For me this is a loaded question. But there are many factors to it.
- Stu Hart: Installing too much seriousness into the Family, along with the discipline.
- Bret Hart: Too much pride in his family, treating too much of what defines them with Wrestling; like with the Von Erichs.
- Vince McMahon: Destroying the Regional Promotions first and then destroying Keyfabe.
This is probably a bad analogy. But I would treat it like Shaq playing in today's NBA. Bret Hart was born a decade too late* (correction), he was a perfect product of what 80's wrestling was but he wasn't ready for the late 90's change. That type of professional wrestling wasn't Bret, and he felt betrayed in a sense, like the entire system ingrained on him was no more.
I see with Shaq on Inside on the NBA, he does what any old head does, he talks about his playing days and cannot related to the new product. Only for Bret, this happened during his peak, only he didn't see it because he thought those values still existed.