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Jiraiya, Minato, Kakashi, generally downplays any Akatsuki massively. Itachi gets downplayed too but not as severely.

We can definitely try. Tho I've talked so much Naruto I can't promise I'm gonna be arguing for pages when Bogard enters these threads. Little burnt out on Naruto debates It's mostly an open area, a single boss sized summon would dominate the bridge. IMO that's a scenario that favors Sasuke...

Favor Hebi Sasuke. Jiraiya has larger AoE moves and specializes mostly in them in his base form. Swamp of the Underworld and the toad oil bullet immediately come to mind. But Sasuke had the wherewithal to summon Manda and hide inside him to escape an attack about 50x anything Jiraiya can...

When Sasuke fully mastered the Mangekyou Sharingan during/after the Danzo fight is when I'd be comfortable putting him > Jiraiya's level by a smidgen. His offensive power would be too much for Jiraiya, his Susano'o Arrows likely too fast for Jiraiya to dodge at medium/short range, and Susano'o a...