Itachi for sure, and yes, because he was the most ninja-ish, and probably the most tragic. He's a perfect example of how the best of intentions can lead down the darkest of paths. He's actually similar to Sasuke in that regard, except Itachi's scenario is actually plausible in our world. Sasuke's may one day be plausible given sufficient tech.
"You are not free whose liberty is won by the rigour of other, more righteous souls. Your are merely protected. Your freedom is parasitic, you suck the honourable man dry and offer nothing in return. You who have enjoyed freedom, who have done nothing to earn it, your time has come. This time you will stand alone and fight for yourselves. Now you will pay for your freedom in the currency of honest toil and human blood."
- Inquisitor Czevak
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