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Your mistake is thinking that Tsunade can hold off Sasori. Alone, she has no way of surviving against the attacks of the Satetsu.This fight could go either way as everything we comment doesn't happen that way.
Itachi would be confronted by Jiraiya and Orochimaru and Tsunade with Sasori.
Jiraiya would and should activate Sage Mode.
He should then do Kekkei: Gama Hyoro which will make him sense anything inside the barrier, making him extremely dangerous.
But on the other hand, Itachi could go Susanoo. Itachi's fireballs could be blocked but it could also hit.
Along with Orochimaru, Jiraiya could be able to launch attacks along with his technique that could make him spy on a person as a shadow or even control one with this.
Orochimaru's Eight Branches Technique is extremely powerful. Orochimaru also has Senjutsu.
Itachi would have a little bit of trouble here but since it is against 2 persons, I think J-man and Oro could take this with the right combination unless Itachi could cast a genjutsu on them.
Susanoo is useful yet his stamina is low, so the best bet he could defeat these two is by using genjutsu, some ninjutsu and his weapons.
Yes, Yata Mirror blocks all attacks but not in a 360-degree position.
Totsuka Sword could be countered by speed.
This 2 versus 1 battle decides it all, if J-man and Oro wins, Sannin wins but if not, the duo.
Despite the fact that the Itachi vs Jiraiya and Orochimaru wouldn't happen, I feel that I should also point out that:
- The Yamata no Jutsu would be pointless before attacks such as the Amaterasu.
- Orochimaru doesn't have Senjutsu
- The Yata Mirror does protect 360°
- In this scenario, Itachi is healthy