But what about the tyrant, you ask? Book 9 cleans up the last piece of the structure set up in Book 8 and discusses the constitution of the tyrannical man, the unjust man who stands opposite the philosopher king. You probably won't be surprised to learn that the tyrannical man, and especially an actual tyrant, is a walking civil war. His soul is torn apart by an addiction to all his various appetites. These enslave him, and in this sense the tyrannical man and even an actual tyrant are nothing but victims and slaves. This answers the other part of the question that the dialog began with. Just as the most just man was the happiest, the most unjust man is also the most miserable. No matter how much honor, money, or freedom he may appear to possess, his greatest tyranny is over his own soul.
The most interesting aspect of this chapter is the way that Plato attempts to judge the tyrant immanently, that is, only on the basis of what it feels like to be tyrannical (577a). It's important to emphasize this lest we slide into interpreting Plato through a christian lens. No doubt, there are many points of overlap, but Plato has no notion of sin and judgement before God. So when he tells us that the tyrant's waking life is like a nightmare (576b) and that he is completely possessed by the anarchic desires most of us only experience in dreams (574e), this isn't to suggest that the tyrant has sinned or that his desires are even fundamentally different from a just man's. The problem with the tyrant is instead that his inner constitution lacks any ruler beyond the momentary gratification of pleasure and avoidance of pain. Tyranny, ultimately, is just an internal anarchy. The tyrant merely bounces between his various unsatisfiable lusts and his fear that others will prevent him from gratifying them. Plato sees this disorganized state, constantly at war with itself and everyone else, as inherently miserable, regardless of what outcome it produces in the world. In fact, the more real world power and wealth the tyrant amasses, the greater his greed and paranoia grow, so that the worst thing that can happen to the tyrannical soul is that it successfully becomes a true political tyrant (576c)! This immanent form of judgement doesn't require any agreement about what specific actions are right and wrong, moral and immoral. It only requires Plato's assumption that an ordered harmony feels better than discord.
Socrates isn't content to leave the judgement there though, and instead tries to insert two more immanent proofs that:
... the best, the most just, and the most happy is the most kingly, who rules like a king over himself, and that the worst, the most unjust, and the most wretched is the most tyrannical, who most tyrannizes himself and the city he rules (580c)
Unfortunately, each of these introduces another assumption that the modern eye recognizes as an injection of transcendent value.
First, he contends that the philosopher is the only one that experiences the unique pleasure that corresponds to each part of the tripartite soul (581e). Those ruled by their appetitive part (eg. a money-maker) never know the pleasures of honor or philosophy. Likewise, those ruled by their spirited part (eg. honor-lovers) don't admit the value of money and reject philosophy as "smoke and nonsense". The philosopher, while he values the pleasure of learning above all, nevertheless admits that money and honor are both necessary and can also be pleasures. Naturally, each type of soul thinks that the particular pleasure that corresponds to itself is the most valuable. But only the philosopher has experienced all three pleasures, which puts him in the best position to judge between them. This would have been a relatively convincing stopping point in the argument. But Socrates, perhaps under pressure from his own contention that experience alone can never by the basis of philosophy, mars the immanent criterion by introducing the idea that judgement must also involve reason and argument (582a). Of course, these belong solely to the philosopher, and constitute a special kind of experience we call knowledge. So the argument which at first appeared an immanent comparison of actual experience ends up invoking a transcendent experience, and we conclude that:
A person with knowledge at least speaks with authority when he praises his own life. (583a)
Second, Socrates tries to convince his companions that only a philosopher knows the true definition of pleasure. Sure, every type of soul thinks that its particular pleasure is the most delicious. But much of what the appetitive or spirited souls take to be pleasure is simply the absence of pain (584c). Which is to say that most people operate with a relative hedonic scale. Pleasure, for these souls, is just the temporary satiation of some painful urge, like hunger or thirst. By contrast, the philosopher operates with an absolute hedonic scale, and knows that true pleasure, a pleasure which never wears off, lies in being filled with knowledge (585c). Again, this argument is meant to present an immanent criteria of happiness as more, and more lasting, pleasure. But we can all see that Socrates has smuggled in the transcendence of knowledge and truth, as well as the transcendent supremacy of being over becoming, the permanent over the evanescent.
In the final analysis, I don't think there is one particular value that's transcendent in Plato. Justice, harmony, unity, truth, knowledge, pleasure, the fine -- these are really all synonyms who point to the underlying unity of analogy that constitutes the form of the Good. In a sense, the Good is nothing but the ever-extending analogy that lets us see one good quality after another. This is perhaps why the Good is so difficult to explain. An analogy has no true root. There's not one thing which is the "most analogous" among analogs. All we can do is construct pairwise correspondences. And yet, when we have amassed enough of these, we feel we've isolated some abstract central term which is the essence of the analogy, just like we feel we have extracted the number 5 from many analogous collections of fingers and toes. The Good has the same type or level of reality as a number. At its best, a calculus of the Good would found a science of quantitative comparison of ways of living. That's the only way we can calculate how much better and happier the just man is than the tyrant: 3^2^3 times.
Then, turning it the other way around, if someone wants to say how far a king's pleasure is from a tyrant's, he'll find, if he completes the calculation, that a king lives seven hundred and twenty-nine times more pleasantly than a tyrant and that a tyrant is the same number of times more wretched. (587e)
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