If Kirk's the villain then not only do I root for the villain for the first time, but I'm also confident that the heroes will lose this one.
It seems like I remember a TV Guide article from several years ago that compared the various captains. The writer posed a scenario where Kirk and Picard would encounter each other and have a misundertsanding that resulted in the two facing off. Then, he wrote, "Picard would call a halt to things suggesting that the two of them talk things out and Kirk, of course, would then take that opportunity to kill him."
In all seriousness though, I think everyone forgets that Kirk was actually quite the diplomat when the situation called for it. He just knew how to kick butt and take names when other methods were required.