(ignore me, will you)
Itachi is a total loser, and a weakling. His only useful power, Tsukiyomi, turns seconds into days so he can torture other ninjas with his emo self. He was killed by a disease of all things.
Looking at it another way, he was afraid of Jiraya and said that it 'wouldn't matter how many men we had against someone like him'. Jiraya killed by a 7 man team. Great insight, Itachi has. Then there is the crap with his village. Lets see: kill my family, friends and entire clan in order to 'save the village'. Sure, no other option. He couldn't ahve spared a few of his clan, right? Certainly he had to torture his brother. I mean the man is supposed to be a pacifist but he kills everyone he loves.
Itachi is a waste of ink, and he has managed to make the same of his brother. The series would be so much better without him.