The tyrant is always among the most important figures to understand.
What initially surprises people reading of the tyrant is that he is not an ugly, deformed brute. Callicles is not repulsive, but sophisticated, a college man. Alcibiades is among the most charming of young Greeks. The tyrant is in fact quite clever, witty, usually handsome and affable, always eloquent.
What else strikes us as odd is that the tyrant almost invariably arises out of a democracy. Democracy breeds tyrants. We are loath to hear it. But we are also reluctant to examine the guiding spirit of the actual regimes we designate as "democratic."
A democracy is a regime in which "freedom" rules. Here "freedom" is defined, not as allowing us to follow what is virtuous, but the relativist permission to do whatever we will. The democratic regime makes no judgment about right or wrong. As a result, right and wrong are defined by the polity, from which no appeal is permitted. Nothing is higher than civic will.
A regime in which anyone can do whatever he wills has no standards. It soon swerves about aimlessly like the ship in Plato's Republic VI. The young tyrant sees that no one stands for anything. He conceives himself as the savior to order this social chaos. His own empty soul is motivated by fame as much as by power. He wants everyone to think and say that he "does good," whatever he does.
At the end of Republic I, Socrates broaches the question: Is the tyrant the happiest of men? He can command whatever he wants. He surrounds himself with those who will do his will, tell him what they think he wants. He begins to have "body guards." Not only is he "happy" because he can command what he wants, but, even more subtly, he can order everyone else to his private happiness. His good is the common good. All are ordained to him and praise him.
When we come to the end of Republic IX, we see that the tyrant, who uses everyone else for his own purposes, turns out to be, not the happiest of men, but the unhappiest. He can trust no one. Every relationship with him is tainted with fear or false adulation. Like Nero in the description of Tacitus, no one dares to contest with him in any field.
Yet, as Aristotle remarks, the tyrant wants to be loved. He craves public admiration. He arranges many public appearances. He wants people to tell him that he is nobly serving them. Of course, love is not the proper relation of ruler to ruled. Justice is. The confusion of love and rule was pictured by Allan Bloom in the case of King Lear. He wanted something beyond politics, love for him, to be a political test.
The dialogues of Plato are filled with promising young men who come to Socrates to learn how to rule. Socrates is coy with them. Their souls are disordered. They want power without discipline or insight. They want to learn to speak persuasively. They want to sound good, not be good.
The tyrant only hears what he wants to hear. A tyrant must prevent friendships among the people, Aristotle noted. Friendships imply something beyond the tyrant's control. But the tyrant has no real friends of his own. He cannot tell why people surround him. He is not sure of the advice he is given. He only hears what people think he wants to hear. The tyrant becomes more and more isolated. He cannot go out in public without his body guards. He is essentially alone.
The tyrant acknowledges nothing higher than himself. Still, the tyrant himself wisely leads an ascetic life, no drinking and carousing, as brutal tyrants do. Everything must be public. People must be kept busy, stimulated. They must build pyramids; they must be kept employed preferably beholden to the tyrant's regime.
The modern tyrant has the advantage not only of being in control of the military but of the means of communication. Though the tyrant rules for his own sake, he insists that his rule is beneficial to everyone. Only traitors have any criticism of him. Nothing transcendent is allowed. No judge exists but himself of his own actions.
Tyrants can last. People adjust. Their souls become lethargic. The tyrant often dies in bed, much admired. The souls of citizens reflect the configuration of the polity. The tyrant has taken the measure of freedom. Tyrants are safe so long as, in their souls, people define freedom as the doing of whatever they want.