Syracuse

The most powerful Greek city in the western Mediterranean. Plato traveled here three times, hoping to shape a philosopher-king, and failing each time.

Syracuse was the richest Greek city in Sicily and the place that ruined Plato's confidence in politics. He went three times hoping to train a ruler in philosophy, and each visit went worse than the one before. On the first he was reportedly sold into slavery and had to be ransomed by a friend who happened to recognize him. The younger Dionysius turned out vain and impatient. Plato left for the last time in 360 BCE having accomplished nothing, and everything he wrote afterward about philosopher-kings carries the mark of it.