I am not sure about this one at all. Because, there are some things which are quite interesting about Ar-P, however, I am not sure if he "deserves" to win this one. I mean: he is neither any fascinating evil character (rather a misguided fool), nor a great character with some amazing character trait (can't think of any), he was perhaps only a cool conqueror, yes, that is true. I am quite amazed by his victory over Sauron - imagine the massive army he must have had, had to be quite impressive assault - and this monument they raised in Umbar to mark his victory there. It has something quite realistic in itself - it is said that despite all the horrible deeds Ar-P has done, this victory was always held by the Dúnedain in memory as something to be really proud of in their history, and to be proud of Ar-P, that means, consequently. (I am kind of comparing inside my mind - our history/ies are full of characters of kings and leaders like this; the first I now thought of, if I imagine let's say Stalin, it was probably something very similar, he was praised for what he did in turning back the Nazis and eventually beating them on the eastern front. One cannot deny him this, whatever his other deeds were like - of course, another thing are also the uncountable dead even in the war because of the way it was fought...)
Well, seems like I made it clear for myself after all through some reflection on the course of writing this
++Ar-Pharazon the Golden