It’s funny how time and the recent movies altered my perception of the character Jim Kirk. I’ve rewatched some of the original episodes in order and original Kirk is both smarter, more controlled, and more haunted than I remembered. Of course they’re also all a lot more sexist.
Captain Kirk has an unfair reputation as being the 'cowboy diplomat' captain. Admittedly Kirk does do his fair share of rule breaking and risk taking, but he's a man who ultimately understands both the burdern and loneliness of command.
I'm thinking the only time he practiced cowboy diplomacy was "A Taste of Armageddon" . Everything else was at Starfleet's request.
Kirk was a very by the book Captain. His orders were generally open for interpretation until they weren't. He didn't flagrantly disregard orders often (Amok Time was one of the few) and his rep for being a rule breaker comes from the films more than the series.