Itachi should be about equal to Madara; they have the same abilities and high intellect. I'd say that Itachi is a little weaker, but this is negated by power over spill from Jiraiya compared to Minato, who vastly outstrips him. The real question is Nagato vs Hashirama. Personally, I think the problem here is that Jiraiya is too weak compared to the other 5, and once he dies the fight is over. Plus, the teamwork on team Itachi is much stronger; ignoring the hate between Madara and Hashirama, Nagato can bring the other two back from the dead and pull someone into a Totsuka stab, Minato can teleport them out of bad positions or warp away powerful attacks, plus he can instantly take advantage of any openings the others create, Itachi can guard with Yata shield and create openings with genjutsu. Finally, all 3 have defense-ignoring insta kill moves. The other team probably has some equivalent possibilities, but the three of them are more oriented toward individual combat, plus stuff like Amaterasu, Jiraiya sound genjutsu, and Hashirama massive forest growth can cause friendly fire. And before this is pointed out, yes Itachi has Amaterasu, but he doesn't have to rely on it as much because of Totsuka sword.
