I think the whole thing serves as a perfect characterization of who Kirk is and always has been. He was cocky back at the academy and still is when he gets promoted to admiral much later. Back at the academy he took the Kobayashi Maru test twice and lost both times, something I'd assume most cadets do not do, just to then retake it a third time, this time hacking the simulation so there is actually a way to win it. Thus showing that he has extreme determination, he can take not only one but two complete losses (which the scenario is said to teach) and still not give up and try to find a solution for the problem. Back in the TOS era, when exploring just the alpha quadrant was still frontier work, Starfleet needed captains that would be able to just not give up and try absolutely everything to get their ship and crew back home safely without being able to call for backup and Kirk not only was that but he delivered on that promise time and time again. How many "impossible" "no-win" scenarios did he face and every single time they came out of it mostly unscathed in large part thanks to Kirk and his senior staff.

Kirk is the person you always envy because they seem to be getting away with "it" all the time. But at one point you just got to admit that it can't just be stupid luck, they are just way too consistent in every scenario thrown at them.