Originally Posted by Nejifan
Why would you assume pity? Kabuto handled Sage mode perfectly fine. If itachi didn't have izanami he would have been able to beat sasuke and itachi at the same time, which, even with all the power creep we've seen, is **** impressive.
For all we know, he handled sage mode flawlessly. I could understand pity for losing, but not for "I knew you couldn't handle sage mode". That wouldn't make sense.
Orochimaru comes off as the guy that foresaw everything. He knew Sasuke would crave the power to train with him, he knew that once he was "killed" Sasuke would hunt down Itachi, which he wanted so he could attempt to take his body again, then when Sasuke revived him from Anko's mark, he acted like he knew that all along (and admitted he was able to see everything occurring and felt like it "wasn't worth the effort" to partake)
So, to me, it appeared he pitied Kabuto. Kabuto himself was always trying to impress Orochi by being what he thought he wanted. Be it a spy, an aide, a medic, and if Orochi had wanted, a vessel (he even got that wish when he implanted part of orochimaru in him) and Kabuto knew what would impress him was power. So he went for sage mode (something that without the orochi implant he himself admitted wouldn't have been possible) and had thought himself the most powerful man in the world because of it. I'm sure even without Izanami Itachi'd have found a way to beat him, and Orochimaru knew that. He knew Kabuto was nothing but a failure just trying to impress him, and for that pitied him.