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Which one of them plans ahead better?
Shikamaru by default, just look at Itachi's life long plan......lol FAIL!

itachi came up with a plan that would last his whole life.
Erhmm you mean that one that he himself said was a failure?
O/t: I say shikamaru, he is said to plan out 200 alternative strategies that's ridiculous. Plus shika doesn't have any insight advantages like the sharingan yet he still easily on itachi's level - which would make him overall better.
Erhmm you mean that one that he himself said was a failure?
O/t: I say shikamaru, he is said to plan out 200 alternative strategies that's ridiculous. Plus shika doesn't have any insight advantages like the sharingan yet he still easily on itachi's level - which would make him overall better.
not even a chance for Shikamaru ... not against Itachi .
unless Shikamaru finds out how to block Sharingan vision area , and then control with his shadow Tech. ,but anyway even if does it , he will only delay itachi's victory
Itachi>Shikamaru . xd
This isn't a fightclearly you meant itach shikamaru orr kakashi
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dem manga facts better sharingan then sasuke