What are you talking about, Shikamaru thinks 5 steps ahead then itachi when it comes to battle. That's his specialty. If he wants to take over his will he has to be more optimistic then his dad. We are also not talking about fighting but more of thoughts given to be more strategic. It's like a game of cards, you can have the best cards in your hands but if I set out a process in my head and play smart I might overcome and have the advantage. How do you think chess is play?
This isn't chess. How long would it take Shikamaru to come up with a plan? You think the enemy will let Shikamaru sit in his thinking position and come up with a plan? If it is not a fight (some kind of mission) then yea I'm sure he can outsmart the enemy.
I don't recall which chapter but somebody said that kakashi was smarter than shikamaru, better sense of smell than kiba and something else. Obviously he did not mean IQ but in battle when he said smarter.
Part 1: Kakashi is smarter than shikamaru, sense of smell better than kiba, taijutsu better than rock lee and sharingan better than sasuke.
The one about sasuke is def wrong but unless shikamaru increased intelligence in the space of 3 years, kakashi is smarter and itachi is even smarter than him.