Kakashi:
1.) Survivor
2.) hella skilled
3.) secretive
4.) Chidori/Raikiri
5.) ONLY ONE sharingan (and can still kick ass)...and last but not least...
6.) THOUSAND YEARS OF PAIN!!!

Itachi:
1.) Got damn, he killed his family!
2.) God of Sun AND God of Moon
3.) Mangekyou Sharingan
4.) ...he's an Uchiha
5.) He's just way cooler than Sasuke

My Answer: Kakashi
My Reason: Thousand Years of Pain