Plato's first visit to Sicily in 388 BC had ended badly. Twenty years later, he would try again. And again. Both attempts would fail — but they reveal something essential about Plato's character and his philosophy.
Second visit (367 BC)
Dionysius I died in 367 BC. His son, Dionysius II, inherited the throne. Dion, Plato's friend and student, saw an opportunity. The new tyrant was young, impressionable. Perhaps he could be educated into becoming a philosopher-king.
Dion invited Plato to Syracuse. Despite his earlier experience, Plato accepted. He was now sixty years old. If there was even a small chance of realizing his political vision, he had to try.
At first, things seemed promising. Dionysius II showed interest in philosophy. Plato began teaching him geometry and dialectic. But the young tyrant lacked discipline. He was easily distracted, more interested in appearing philosophical than in actually thinking.
Worse, Dionysius became jealous of Dion's influence. He accused Dion of plotting against him and exiled him from Syracuse. Without Dion, Plato had no ally at court. The experiment was over. Plato returned to Athens in 366 BC, frustrated once again.
Third visit (361 BC)
Five years later, Dionysius II invited Plato back. He claimed he had changed. He wanted to recall Dion and resume his philosophical education. Plato hesitated but ultimately agreed — perhaps out of loyalty to Dion, perhaps out of stubbornness.
This third visit was a disaster. Dionysius had no real intention of recalling Dion. He kept Plato essentially as a hostage, showing him off to visitors as proof of his cultural sophistication. Plato was trapped in Syracuse for months, unable to leave safely.
Finally, Archytas of Tarentum — Plato's old Pythagorean friend — intervened diplomatically and secured Plato's release. Plato returned to Athens in 360 BC, now nearly seventy years old. He would never attempt political reform again.
Why did Plato keep trying?
Three failed attempts over twenty-three years. Why? The Seventh Letter (if authentic) provides an answer: Plato believed that unless philosophers became kings, or kings became philosophers, there could be no end to the troubles of cities — or of humanity.
This was not naive idealism. Plato knew how difficult it was. He had witnessed Athens execute Socrates. He had seen tyranny up close. But he also believed that philosophy had an obligation to engage with the world, even when the odds of success were small.
The Sicilian adventures represent Plato at his most human: stubborn, idealistic, willing to risk his safety for a principle. They also show the central tension in his thought: the gap between the ideal and the real, between what should be and what is.