Toki

I believe that shikamaru would realize the great diffrence between his own physical capabilities & kakashi's then plan accordingly, but he would also make certain that he had some way of dealing with the sharingan & raikiri. Theres is no doubt that he would take the time to figure effective counter measures & set up amazing traps that could even catch Kakashi off guard(especially if he was not expecting anything.) But as already mentioned Kakashi is full of powerful techniques that could tire shikamaru out quickly having to avoid or manage to counter them somehow. Infinite prep time & the element of surprise do push things in shikamaru's favor considerabley but does shikamaru know about all the jutsu & taijutsu that kakashi has copied with the sharingan as well? If kakashi has fully memorized some of those & saved them for emergencies he too would have an element of surprise for shikamaru. If shikamaru had at least one truly powerful jutsu, I would say he most likey wins, but as things are i might have to call it a tie.

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