7. Time Travel Carelessness
Look, nobody's really an expert on the whole time-travel do's and don'ts, but going off of what we know of the Star Trek universe and what Kirk knew up until this point, it's never really a great idea to allow people to split up and get lost in another time period. Which leads me to the next highly questionable decision of Jim Kirk: A lack of logistical common sense. As Kirk and crew land in San Francisco, circa 1986, it always bugged me a little that he so willingly splits everyone up into teams, during a period in Earth's history that was Terra incognita, aka the unknown land, according to Kirk himself! Additionally, if he learned anything from the last time he and some members of his crew were sent back in time, via the Guardian of Forever, he should have recognized the inherent dangers of the crew being separated from one another. That would I don't know, maybe limit the amount of damage done to the timeline they know and love back in the future, maybe? However, he was having none of those concerns here. In fact, he even joyfully handed out cash flow to his crew on the streets of San Francisco before they went off on their own. In the end? Chekov almost dies from brain damage, on top of almost being captured by government officials of that time-period. Great Job Captain Kirk! Granted, the mission was completed in the end but come on now, Kirk's master plan could have accounted for a little more common sense than what it did, right? Nope, not in this case.