Itachi is a pretty cool guy eh, kills his entire clan and doesn't afraid of anything.
Itachi loses in the end though, Sasuke almost dies in the fight too. As mentioned, Itachi only loses because of his illness and failing eye sight from the constant use of his Mangekyou Sharingan. According to other people Sasuke has a Mangekyou Sharingan when he kills Itachi. Pictures anyone?