1. Complacency With Raising The Shields
Look, as far as this list being in an order of least worst to the pinnacle of Kirk's questionable actions (or inaction in this case), it's not. However, this particular mistake of his truly stands out as the most glaring of my top ten. When Admiral Kirk decided to wait far too long to raise the shields as the starship Reliant approached out of nowhere, with no standard hails or communications, it was a complete and utter blunder on the part of the Admiral to have become that complacent in protecting his new trainee crew. Additionally, he had been recently contacted by his ex-wife, Carol Marcus, relaying her imminent concerns over the Federation taking the Genesis project away from her and her science team. You'd think the moment Jimmy boy was alerted to another Federation ship's presence in his sector that he'd have put the Enterprise on the highest alert level possible. At the very least raising the shields should have been a knee-jerk reaction to the unplanned appearance of the Reliant. Unfortunately, even after Lt. Saavik event went as far as quoting the regulations to Kirk, in the hopes of convincing him to raise those shields, Spock put her back in her place and Kirk went right on ignoring the rules. In the end, many trainees were killed when the Enterprise was surprise attacked without the shields being up, including Scotty's nephew, Peter Preston. In my opinion, this should probably go down as the most highly questionable action of Jim Kirk's career! Many of you may disagree with my list and by all means, comment below. Feel free to fill in the blanks where I missed some of Kirk's more mistake prone moments of his legacy.