If u compare them in terms of power definitely I'd say Tobi > Itachi....after all he was working with Uchiha Madara...he would never take a weakling....also he would som1 who is really powerful and smart if was 2 entrust him with his plan...but it is true that if Itachi did find out the result would have been different...i.e. I don't think he would confront him directly but would have found a way 2 free the tailed beasts or somthin...also Itachi is no idiot if at all he confronted Tobi he would just take da statue nd disappear using his sharingan.....also if I was 2 rate the top 5 akatski I'd rate em as
Tobi(Obito)
Pain(with 6 ppl)
Itachi
Kisame
Konan
I do agree Itachi is not ad powerful as Tobi nd Pain(Nagato)....but he is a way smarter shoinobi than them....plus the fact that Itachi found Tobi and took his help 2 kill the Uchiha means that Itachi definitely knew some part of his plan...plus he should have had som other leverage on him if had 2 convince him 2 kill Uchihas...
Kisame
Tobi(Obito)
Pain(with 6 ppl)
Itachi
Kisame
Konan
I do agree Itachi is not ad powerful as Tobi nd Pain(Nagato)....but he is a way smarter shoinobi than them....plus the fact that Itachi found Tobi and took his help 2 kill the Uchiha means that Itachi definitely knew some part of his plan...plus he should have had som other leverage on him if had 2 convince him 2 kill Uchihas...
Kisame