So while it looks like he had some crazy adventures and disregarded Starfleet at every turn, that’s a lie.
Most of the time, he spent every other episode calling back, following the strictest of laws, going through proper motions and channels. Every other action was court-martialed and brought to trial. He was, for the most part, a dedicated captain following Starfleet’s rules.
Just because he is now the reason for about two dozen more rules, doesn’t make him the crazy madman adventurer we see him as. Of course he differed from his orders, at times. But those are the most excusable times, and even then, after disobeying, he laid himself up for proper discipline. He knew he’d done wrong in the eyes of his superiors, but his conscience wouldn’t have let him do any different.
Kirk was a rule follower and a rule maker. And only on special circumstances, a rule breaker.