Shikamaru vs Sai

Suggested by Sonic This is a pretty close fight. Shikamaru has really mastered his Shadow possession jutsu and various other versions where they can actively attack an opponent. At the same time, Sai’s Taijutsu is easily superior and he can create a ton of animals through his ink to keep Shikamaru busy. I see this being a very strategic battle but ultimately I think Sai will pull ahead. Taijutsu is very important in a battle like this where both ninjutsu skills are around equal. Shikamaru would be able to win with prep time but in a straight up fight I’d say it’s his narrow loss. Sai wins.

Riddler vs Sai

The Riddler has always tried to be a smart guy. His riddles have even gotten Batman confused at some points! Of course Sai doesn’t need to solve the riddles. He just needs to take Riddler down. That shouldn’t be too hard for someone like Sai. Sai has his speed and ninjutsu. Sai wins.