Oh, definitely. Orochimaru's honestly the most criminally underrated ninja, only because he's being constantly beat in order to show off just how strong Sasuke or Itachi are-- it's incredible how the best characters are the most mistreated by the plot, isn't it? Anyway, Orochimaru's undoubtedly one of the strongest shinobi in the NV below the people with kekkei genkai and especially dojutsu. I wouldn't say he 'outsmarted' Itachi, though, since... Itachi did have him beat, but he managed to come back anyway via Sasuke. That's planning ahead, not really directly outsmarting. It shows how good Orochimaru is at contingency plans, not that he managed to completely outsmart Itachi.
I like Itachi and Orochimaru. They're some of my favorite characters, and I honestly do wish they had a legitimately interesting fight rather than Orochimaru getting genjutsu'd or Totsuka'd. That blame's on Kishimoto, though.
Anyway, Orochimaru proved the power of his chakra by controlling three of the four Hokages, only unable to fully control Hashirama whose chakra is legendary, exerting the power of his own chakra over three of the four most powerful ninjas in the verse, and with how he never seems to actually overexert his chakra, only the body he's inhabiting. I mean, have we ever actually seen Orochimaru go all-out while not in a decaying body? Even then, we saw him casually fighting off Naruto when his body was physically rejecting him and having the ability to off early Shippuden Sasuke while he was literally on his deathbed. There's no denying it, if Orochimaru wanted to just kill Sasuke rather than take his body, Sasuke would be dead.
This was generally a cool thread showing off Orochimaru's chakra. +Rep.