"How did this one person rise to such a position? Why does anyone go along with this?"
From the inside, the very same situation seems obvious:
"Oh, it's always been like that."
After awhile, people don't even blink to acknowledge it.
The difference between the dysfunctional group and the functional one is insularity.
Keeping to oneself, never letting in an outsider, never learning from best practices, refusing training, staying away from conferences, avoiding networking with unfamiliar people, shunning social media networks, and being too busy even to crack a book or a magazine that you usually don't read --
All of these are a breeding ground for mental bacteria. The kind that thrive on dictatorship. Insular thinking, because it leaves you unaware of common norms, strips you of confidence. You end up wanting to be told what to do, often abusively; rewarded for total obedience; punished for asking a question; and accepting it when you are made to do things in an insanely unfair and inefficient way "or else."
The worst misconception people have about dictatorship is that if they comply, they will be spared. Not true.
Anywhere you work, anywhere you live, if you see insular thinking taking root, challenge it. Bring forward external perspectives and a critical approach. It is neither "rude" nor "weird" to do so.
Where you see a dictatorship blossoming, nip it in the bud.