Critias ( 460-403 BC)

Leader of the "Thirty Tyrants" that ruled Athens 404-403 BC. The rule was one of terror, and Critias has gone to history as one of the ultimate villains.

Critias was born into an aristocratic family, and was educated by the likes of Socrates and the Sophists. He was both the uncle and guardian of Plato's uncle Charmides, and Plato described hem both as young, glamorous men in his dialogues.
After the incident with the mutilated Herms (see Alcibiades) in 415 BC, Critias was suspected of having taken part in the vandalism. He was arrested for the crime, but subsequently released.
In 411 BC, Critias asked the Assembly to call back Alcibiades, but eventually he was exiled to Thessaly after the Assembly had turned against Alcibiades again.

At the end of the Peloponnesian war in 404 BC Critias was called back when the Spartans demanded it in the peace negotiations after they had defeated Athens.
On his return he was elected to the dictatorial, Sparta friendly government that consisted of 30 tyrants. The rule can be compared to extremist fascism where anyone suspected to resist or had great personal wealth was executed. In Eleusis a mass execution of 300 men was ordered.
In 403 the 30 tyrants were toppled, and ironically, Critias did not die then, but in a common street fight in Pireus. He was well hated by then, and was one of the reasons Socrates was persecuted, since the philosopher had been his teacher.

Apart from being a villain, though, Critias was intelligent and cultural and wrote prose, tragedies and lyric poetry.