The smartest? I wouldn't say Kabuto...leastwise, he may be smart but he doesn't have much common sense.
I'd say each person has their strengths...Kakashi is a technique genius, Shika is strategy, Tsunade and Kabuto are medicine, Oro is a developmental genius (having created some pretty "out there" stuff)...
In terms general intellegence (aside from possibly the Akatsuki leader, whom we don't really know about), I'd say the smartest person is probably Nara, but that's far from the end of the discussion. *shrugs*
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