Well the title is a little missleading. This was most likely brought up before but i'll give it a try anyway. I have come to believe the the Uchiha Clan and the Kyubi may be very much interconnected. Take a look at these pages: Should I spoil Tag These? The most important information lies on the bottom of the first page and the top of the second. Sasukes response reveals a few important things to us: 1). For one, he has knowledge of the Kyubi. It is possible that Orochimaru told him of the Kyubi. But I think it would be a lot more interesting if the secret of the Uchiha/Sharingan, of which only Itachi and Sasuke are aware of to the best of our knowledge, is somehow connected to the Kyubi. 2). Two, lets analyze Sasukes words. He says "Well it would appear this isnt the first time you gazed into eyes such as these...which would make you...the Nine-Tailed Demon Fox on doubt." This directly tells us that the Kyubi is aware and related somehow to Uchiha/Sharingan and that Sasuke is aware of this relationship. Also look at the bottom left of the first page. The Kyubis eyes suddenly become much more narrow and focused. It is at this point that he possibly realizes, Sasuke is aware of the Uchiha Secret, which would also indicate that the Kyubi is aware of the Uchiha secret. Now this brings us to Madara. The Kyubi brings up Madara, at which Sasuke suddenly narrows his eyes and takes his hand away from the Kyubi. This could possibly suggest that Sasuke has knowledge of this name, and that the person Madara may also be connected to the secret. Since Itachi also has knowledge of all of this, I would presume he also may have knowledge of Uchiha Madara and may in fact tried to seek this person out, considering he is still alive. It may in fact be possible that Madara is the oh so mysterious Akatsuki Leader. This would parallel my Uchiha Madara = AL Theory quite well. If you havent taken a look at it already you should. Heres a link: Link removed Thanks to rorykage. His contribution to my Uchiha Madara = AL Thread is what sparked my interest in this topic. THIS A ONLY A SPECULATION/THEORY. NOTHING HERE IS 100% FACTUAL!