One of ST: Discovery's seasons arcs deals with that dualism in a solid and nuanced way: Two captains, one being more of a agent of chaos (like Kirk), the other being a straight by the book and in the end they both acknowledge each other's approaches because different circumstances require varied approaches to solve.

I think manipulating an unfair situation to your advantage, as long as you don't harm others, can lead to a more creative perspective. Kirk was great because he had a competent crew that he intimately knew and they either followed his command or questioned when he was out of line. In the end he died in his 70s and saved the day doing so. 🌚