Raven

Just because he has the knowledge doesn't mean he could do it by himself. I mean look at the fact that Shikamaru always runs low on steam early...I have no doubt he'd have a great plan, but actually going through with it is another thing. Kakashi is both faster, stronger, and has far more techniques. I still think Kakashi would own him but I'll leave it at that. I mean let's say we exchange Kakashi for Shikamaru in the vs. Hidan and Kakuzu arc. How would Shikamaru have faired against Kakuzu with knowing all of his abilities? How would Kakashi fair against Hidan?

Chiyo had knowledge of how to defeat Sasori and knew about all of his abilities, yet she could do nothing by herself. She had to use Sakura for close range attacks, and if Sakura was not there Chiyo would have gotten beaten to a pulp.

I mean we can even go as far as to think up ideas of how Shikamaru could use defense to disable Kakashi's offensive moves. How would he stop the warp technique? How would he counter Raikiri? What would he do against his mastery of substitution and stronghold on taijutsu as well? Let's not forget Shikamaru usually has intelligence over his opponents in general. Now he's facing someone who is on his level plus more experience. I would easily say that Shikamaru would have an easier time with Kabuto over Kakashi even though it was stated that Kabuto is equal to Kakashi.

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Favorite Quotes:
"Everyone dies, it's a natural part of life. But if your life has no meaning you're already dead." -Wolf's Rain, Kiba

"Humankind cannot gain anything without first giving something in return. To obtain, something of equal value must be lost."
-Fullmetal Alchemist, Alphonse Elric

"It's not what folks say...it's what you answer to." -Madea Movie, Madea

"Deploying resilience is more important than being a prodigy." -Life, Me