Summary: (Itachi, Madara) In a way he was a parent-figure. SPOILERS FOR THE LATEST MANGA. YOU BE WARNED!!
A Hundred Years Ago
Tobi would catch him on his own sometimes. Before there was Tobi there had been other people, strangers in bars, familiar shadows in dark allies, rustlings in the trees at night. It might have been creepy if Madara had done anything to truly hide his presence. As it was, he did the bare minimum required to arise no questions in Akatsuki or outside it.
And he visited often. Not so much that he suffocated, but often.
Itachi would be alone, usually quietly reading or thinking or occasionally training. Madara loved in particular to enter his Genjutsu uninvited, always very gently. They would talk for hours (a lot of family history, but other things also, Madara knew something about everything and was willing to share) and he would look like he was sleeping, at least as far as Kisame was concerned.
In the Genjutsu, he would pick the most fantastic locations for their conversations. The Valley of the End at sunset, the water beautifully rendered. Never Konoha, but sometimes one or two of the Uchiha Clan's older hiding places, familiar in a haunting way, as from a children's tale. The Rain during a celebration, walking among a crowd of imaginary shinobi, watching the fireworks. The far-away sea Itachi had seen only a handful of times. The desert, on a milder day, or when real-Itachi was miserable and cold. Madara had travelled the world, and he understood understated beauty.
"How are you doing, Itachi-kun?" He would ask. Very often it was a silly question – Itachi was being watched, after all. He knew his movements were being tracked. But in some hard to define way it was comforting that he would ask.
Itachi always gave an account of his recent activities. Madara would say, "And how are you doing, Itachi-kun?"
Madara had been watching him, for a long time most likely. The weight of that was strangling, thinking of going to school before the war, of graduating to Genin, all with these eyes resting on him. Cataloguing his strengths and weaknesses.
Yes, Uchiha Itachi had trouble at home. His parents were not very affectionate. They would not ask how he was doing unless they meant to know how his schoolwork went, how his missions went. To differentiate himself Madara made a point of asking. A stupid, cheap trick, but he'd answer anyway because whether he knew this or not (Itachi would get confused as to what he was and was not supposed to notice) Uchiha Itachi did not lie to Uchiha Madara.
"I'm tired." Or, "My eyes are getting worse." Or, "I'm so sick of waiting for Sasuke." Never anything good because that would be too much of a lie, and anyway, he was here to vent his various frustrations. Playing a sullen teenager came surprisingly easily.
Madara would say something comforting. Not often anything useful, though sometimes… A war here, avoid this place Or, Konoha on the move here Or, Orochimaru wants your eyes. You'll have to defend yourself.
Keep going, Itachi. We'll manage through eventually.
This too was different from his parents. His father only ever told him bluntly what had to go where. He was not someone to sugar-coat anything, even perhaps things that were best left unsaid entirely. His mother glossed over everything, but in a kind of frightening way that exposed the underlying truths. Whether she did this on purpose, Itachi never knew.
Madara did not lie, as far as he knew. He withheld things. When faced with this he would say that he did it only for Itachi's own good. He was still a very young boy. He did not need to deal with these problems.
That he had dealt, already, with the problem of his clan and the problem of his eyes and the problem of his brother was apparently not enough proof of his abilities.
No, Madara knew Itachi. He had watched him, likely for years before making his appearance (no, Itachi no longer believed he'd found him out unassisted). Itachi suspected, in the very small part of his brain that still knew this information, that he had watched also the Hokage giving Itachi that final order to destroy Uchiha Madara, along with the rest of his people. But this secret was too great even for him, he wilfully ignored it. If Madara knew…
If Madara knew and did nothing, then Itachi himself was inconsequential. That would be too much. He did not need to know this thing. And if he knew and was waiting to spring his trap then Itachi was already caught, and in a way had no wish to escape in the first place. If it was not this trap then it would be another, and his time was running out anyway, and Sasuke was as geared up as he was ever going to get. He put these possibilities out of his head completely, along with everything else that he refused to know.
And yet the possibility that Madara had not been watching, that he knew nothing of Itachi from before the moment of their meeting, was in a way even worse. To think that someone born into an era of war, of unimaginable torment, would understand anything of the boy who lived in a rich and secure clan in a rich and secure village, ruled by a soft-hearted Hokage. The idea that the life of a Shinobi was still as brutal now as it had been a hundred years ago went against the deepest things that drove Itachi. If Madara understood him, truly understood him.
This was a thing that Itachi did not wish to ever know. He preferred a villain because if he had no villain he would have to conclude that the parents he killed had been monsters, that the village who'd told him to do so had been filled with monsters, and that his entire life had been spent going between equally insane masters, differentiable only by the color of their eyes. If this were the truth, then the logical solution would be to kill Sasuke, to spare him the torment of such a world, and then to quickly go and die himself.
So instead Madara was a clever man. Even a kind man in his way. He saw Itachi as the son he never had, perhaps the brother he'd murdered. He differentiated himself from the parents who'd driven their son crazy and the village which had driven him right back to them at the end of the day. Itachi's parents had been distant and formal, and so Madara wore a happy mask and asked after Itachi's health often. His parents had been eager to use his talents, so Madara left him to his own wishes:
Go your own way, Itachi. This demon hunt needs you, but don't drive yourself too hard. Live your own way. We will manage without you.
His parents had let him grow up. Madara seemed to forget wilfully that yes, Itachi was even legally an adult now. He could drink, yes, and he understood sex, even if he didn't bother with it. To Madara Itachi was always just this side of fourteen.
All this drove Itachi harder. He refused to be cowed or soothed into submission. Yes, he thought, when Madara had given him a new ribbon to hold his hair in place and a birthday cake he had a great deal of trouble hiding from Kisame the next morning, yes, I will defeat you. Konoha will defeat you.
It was, after all, far, far too late to switch sides now.
END
A/N: I think from the way he talks to Sasuke, Madara had a great deal of respect and maybe affection for Itachi that he couldn't really express, knowing that Itachi wanted him dead. And they must have been in regular contact, at least, through those… what, seven years from the massacre to Itachi's death? Anyway I thought it might be interesting to see what their relations were actually like. At first I thought, they're probably always double-crossing each other, or ignoring each other, but now… why not? Madara truly acts like a real concerned person, not for Sasuke maybe but for Itachi, I think yes. He acts like he wants to use Sasuke, but Itachi he'd left to do as he pleased for the most part, and in a way took him in once his mission for the village was completed. I would think Madara was the one to invite Itachi into Akatsuki. He seemed to be the person who knew Itachi best for that period between thirteen and twenty one.
BTW, that mission I referenced where Itachi had to get rid of Madara was something I completely made up… but imo it's really entirely possible—if that WAS his mission he would have eventually realized that he didn't have enough power to do so anyway and instead just stalled the demon-search until Sasuke got strong enough, and then gave Sasuke everything he could to continue the mission for him, which Sasuke would have if Madara hadn't had a chat with him.
Man I wrote so much. :D
PS: I seriously, seriously hate this website's abhorrence of non-alpha-numeric characters. Sorry but grow up. Those things are helpful for a reason, you fucking idiots-- yes some people will misuse them and we the readers will deal with it. I've complained even but no one seems to care here. Also, am I the only one who can't type the name of the website without getting it erased??