Op, when you make threads like this, you will always get poor arguments and character wank from both sides, as well as bashing. I sincerely hope that you are just trolling. Itachi won't ever beat Maddy.
However, as for some of these comments...
Yes, everyone knows that Madara beats Itachi quite handily. However, insulting one's intelligence is just lame. Also, Itachi is hyped more for his intelligence than Madara is, while Madara himself is more hyped for his battle skills. In effect, you are insulting Madara's intelligence, considering that by manga standards, it's lower than Itachi's. And if you try and say that Itachi failed or whatever, he's human and they all do. Madara failed to persuade his clan to go with him. Also, he attributes his plan working mainly to luck, which is the main reason it worked (though he is quite smart already). He left Black Zetsu to take care of Obito in case he went against the plan, but bz is fodder and Obito would have beaten the tar out of him. The only reason it worked was because Kabuto brought back Madara himself, Obito had no intention of doing so.
@bold- I would have said the same thing, but then I remembered that Konohamaru is the one who destroyed Nagato's precious Naraka path in a record-setting 5 seconds.
Itachi's smart and he wouldn't fight EMS Madara just like that and go charging in. Saying EMS Madara would stomp at laughable diff is serious wank for that character. It's just an exaggeration. However, he would more than likely win regardless, but laughable? That just sounds too harsh imo. He wins, but not that easily.
He made that statement after seeing the weapons. Therefore, he knew at the moment he said that and obviously had some knowlege on their background. He's also considered Madara's will. Not the best point to make, though regardess Maddy does beat Itachi.
@bold-Quit trolling please. Also, discontinue the creation of such threads as this in the future. It only brings unnecessary hate for both characters and a slew of insults.