Board Thread:Versus Debates/@comment-1018594-20150728091344/@comment-6963368-20150729233516

Depending on what you mean by canonical knowledge, individually, most of the Konoha 11 know individual weaknesses of the Akatsuki. The biggest issue wouldn't be pain, it would be Orochimaru. Shikamaru knows about Kazaku and Hidan, Sakura knows about Sasori, Naruto knows about Itatchi, Pain, and Obito. I'm not saying it wouldn't be a hard fight, but were talking about the man who has the strongest tailed beast in him with backup from his allies. If they know of their opponents and their abilities then all they need to do is pool information into Shikamaru and they would win. The only flaw in this is the Konoha 11 don't know the full extent Orochimaru's abilities and would likely get killed approaching him disregarding naruto. Even Sakura and Shikamaru wouldn't stand a chance if they get too close just because of how unpredictable and one shottable his techniques are.