What do you make of Socrates? Was he truly as humble as he suggested when he claimed that the one thing he knows is that he knows nothing? Would...

It's quite clear that Socrates was not actually all that humble, and he seemed to derive great enjoyment from undermining other people's arguments and generally annoying them.Perhaps the greatest evidence that Socrates was in fact quite arrogant is the speech he gave after being found guilty of impiety and corrupting the youth; he could have asked to be sent into exile and would likely have received this punishment, but instead jokingly suggested that he...

It's quite clear that Socrates was not actually all that humble, and he seemed to derive great enjoyment from undermining other people's arguments and generally annoying them.

Perhaps the greatest evidence that Socrates was in fact quite arrogant is the speech he gave after being found guilty of impiety and corrupting the youth; he could have asked to be sent into exile and would likely have received this punishment, but instead jokingly suggested that he be rewarded for his great contributions. His comments were so arrogant and aggravating to the jury that more jurors voted to execute him than had originally voted to find him guilty.

Though not charged with it, he probably was guilty of sedition, as several of his students may have used his arguments against democracy as their motivation for overthrowing legitimate city-state governments and terrorizing thousands of people. 

Indeed, there is a kind of arrogance even in asserting that one knows nothing; it implies that you have such a monopoly on epistemology that you can firmly declare that even the most basic facts (the sky is blue, the Sun rises in the East) are in reality not true facts but only unsupported suppositions. It is essentially an attempt to tear down the entire edifice of philosophy, and other many other philosophers were understandably angry about it.