Socrates was not handsome. He was short, stocky, thick limbed, bow-legged, and large headed. He had a snub nose and protruding eyes, which served him well. His detractors called him a busybody, a buttonholer. He had the ability in extraordinary measure to engage people in conversation, fixing them in the intense glance of his bulging eyes, and to cause them to admit things about themselves that they did not care to acknowledge. And this is how he spent his time.
By a kind of questioning that is not unlike cross-examination, he caused his interlocutors to admit that they were ignorant of the very thing about which they claimed to have expertise: politicians were made to admit that they didn’t know what justice is, nor even whether there is such a thing at all; priests were made to confess that they had no idea of holiness; moralists, of virtue, or at least not a clear or consistent idea of it, one that did not stop moving around and contradict itself.
Socrates presented himself not as a teacher, but as an inquirer, pretending to know nothing, he inquired of others hoping to be made wise by them. The Greek word sophia, generally translated “wisdom,” applied to all sorts of knowledge or skill that enabled its possessors to do something well, whether it be building a house or living a good life. Hence he preferred to be described not as wise, a sophos, but as a philosophos, a seeker or lover of wisdom. Not surprisingly, he often chose as his interlocutors persons of prominence, pillars of society, for these were noted by their expertise. And in a polite and always respectful way, he would unmask them in public, which is a form of humiliation that every public figure dreads. Young men, who had not yet entered public life, themselves often the sons of prominent figures, followed him about and took delight in these practices. They became imitators of him.
In the Apology, which is Plato’s account of Socrates’ defense at his trial, Socrates explained his motives for this activity. Chaerephon, a well connected Athenian and a longtime friend and admirer of Socrates, known for his impetuosity, went to the temple of Apollo at Delphi and enquired of its oracle whether there was anyone wiser than Socrates. The oracle replied that no one was wiser than Socrates. Socrates claimed puzzlement. How could someone who was wise in nothing be the wisest of all? He decided to test the oracle, respectfully, of course, because an oracle is the voice of god, and gods are not supposed to lie. So he began the round of persons reputed for their wisdom, and, by questioning them, discovered and caused them to discover that they were not wise, that their claims to wisdom were only pretense. After many repetitions of this, which invariably made him hateful to many, Socrates concluded that indeed he was wisest of all, not because he had expertise or wisdom in any thing, but because he knew he had none.
This is an instance of Socratic irony. Irony is a kind of ambiguous speech, of saying one thing in a way that suggests another, sometimes just the opposite of what one says. When Socrates claims to be the wisest of all, he is not claiming to be wise. He is wisest because he knows he lacks wisdom, yet that itself is a sort of wisdom. His wisdom is just the opposite of a ‘know-it-all’; when questioning others, he causes them to doubt, because he is more in doubt than they.
Socrates attached great value to this practice, not only for himself, but also for everyone. Critical self-examination was a necessary condition for living a good life. “The unexamined life is not worth living.” By this expression, Socrates did not imagine some silly mystical search for one’s true self, a real identity underlying one’s every day appearances, rather he discovered a truth about himself and others, which is that, to be honest, none of us has anything to boast about. From this very nothing at the core of our being, we begin to enquire how to live. Here the words “virtue,” “justice,” “self-control,” “truth,” labels with vague meanings become our beckoning standards, to be discovered and clarified through a life of enquiry, experiments in living, and critical and relentless self examination. Only by these means can our souls be made perfect, or approach anything like it.
Socrates believed his mission, to philosophize, was intended not only for individuals, but also for Athens, its civil society and government. The institutions of government and those who oversee them must be subjected to the same sort of critical self-examination. Thus the perfection of the soul and the perfection of the city are joined in a common endeavor and this was the purpose of his philosophizing. As he explained to his judges, he considered himself under a divine mandate to engage in such activity until death. He was unapologetic for what he did; there was no compromise; no turning back. If his judges found fault with him because of activity and which he was determined to continue doing, then let them condemn him. He did not fear death. 
Socrates was charged with corrupting the youth and not believing in the gods of the city but by introducing new ones. The court that tried him consisted of 501 men, selected by lot, 50 from each district or “deme” of the city, plus one to break a tie if necessary. The final judgment was 280 to convict, 220 to acquit. Socrates was condemned and executed. Why did the Athenians do this? I have no sure answer. It may help, however, to recall that the Peloponnesian war, which pitted Athens against Sparta, had recently ended with the surrender of Athens. A coup, aided by Sparta, put an end to Athenian democracy, and for a short time, the city was ruled by to so-called “30 tyrants,” one of whose leaders was Critias, a follower of Socrates. This regime was overthrown and a fragile democracy was reestablished. Not long after this, in 399 BCE, Socrates was charged.
After its humiliating defeat, many Athenians came to believe that Sparta prevailed because it was a closed society whose citizens adhered strictly to a traditional law. The wave of new learning, a Greek enlightenment that had flourished in Athens during the previous century, was blamed by many as a cause of Athenian moral weakness and military weakness. Socrates was associated with these enlighteners and modernizers. The radical critique of Athenians morals and institutions that his practice of philosophy required seemed subversive.