Board Thread:Versus Debates/@comment-33197927-20171103070655/@comment-734582-20171103084935

Jiraiya.

Shikamaru is strong and all that, but he still has his biggest weakness: he's a specialist. He's made to be part of a team and his capacity for synergy is god-like, but he's just not that good alone.

Jiraiya on the other hand, we've seen that he has a big bag of tricks and jutsu he can pull from, allies he can call on, and multiple ways to deal with stuff. He's a spy by trade and hardened by battle, so i doubt Shikamaru would be able to corner him in any definitive way.