If you're afraid of saying no when you're uncomfortable in aviation you've got other issues. Anyway...

"constantly looking over his shoulder regarding legality issues & confronting and saying "no" to dispatchers and other management types on a semi regular basis"

Seems like a pretty bold statement referencing a 121 operator in this setting. If I didn't know any better and was reading through these threads in search of information I don't even know what I'd think of those statements.