Itachi/Pain V.S 3 Legendary Sanins

[Turson]

Pain and Itachi takes this with med-difficulty.

 

[Lilt]

Itachi and Pain could each take down two Sannin if they were fighting alone, if not all three. Together, they defeat the Sannin badly.

 

[Genjitxu]

Great thread!
Itachi got this on his own if he's got Toksuka blade and Yamato Mirror. Another way of putting it is this. Remember Yanzo on the cliff? Looking down on the Sanin. Itachi could do the same. Throw in Danzo too if you add a rinnegan user.
Danzo Hanzo, Orochimaru, Jiraiya, Tsunade vs. Uchiha Itachi and Pain.