Dionysius the Elder (c.430-367)

Originally a government clerc in Syracusae, Sicily, Dionysius the Elder sized power and became tyrant, described as the very archetype of the cruel and foolish kind.
Using mercenaries, he tried to expel the Carthaginians from Sicily.

To finance the expedition he plundered temples and took the golden mantle from a statue of Zeus, replacing it with a woolen one with the words that gold was too cold for the god in wintertime. He also took the golden beard of the god Aescleipus saying it was not suitable that the beardless god Apollo should have a bearded father. At first successful, making Syracusae the strongest power in Greek Italy, the tyrant was to be defeated by the Carthaginians later.
> Dionysius the Elder punished crime severely except burglars, since he thought the people of Syracusae lived too luxuriously. He also taxed the people so heavily, that the people complained. He then taxed them even more heavily, until he one day heard the people making jokes and laughing in the streets, which to him meant they no longer had anything to worry about, and so lowered the taxes.
The tyrants' fear of being assassinated is very famous. His bed-room had deep ditches and in order to go to bed he had to walk over a plank, which he then pulled in. He also had a cave built from where he could here everything that was said in the neighbourhood. He would arrest people and have them imprisoned in the cave, where he eavesdropped on them.
One most famous people he had arrested was the poet Philoxenos. One day, the tyrant had the poet fetched, and in front of his court he read a new poem he had written. The people applauded, but when Dionysius asked the poet of his opinion Philoxenos replied "take me back to the prison".
Perhaps the best known anecdote, though, is the one about the persons at court, Damocles. Damocles wanted to flatter the tyrant, and called him the most fortunate man on Earth. Dionysus then invited him to take his place for a day, and had him sit in his seat at a magnificent dinner. At first overwhelmed by the riches, Damocles was then horrified to see a sword hanging over his seat in just a piece of hair.
Apart from being a tyrant, Dionysius the Elder was also a play-wright, competing in the dramatic festivals in Athens