23. Peisistratos Demonstrated the Upside of a Good Tyrant, but His Successors Demonstrated Tyranny’s Downside
A key problem with a dictator or tyrant is that capable and benevolent dictators and tyrants are hard to find. For every capable and benevolent dictator or tyrant who advances the public good, there are many more incompetent ones who leave nothing but misery in their wake. Ancient Athens discovered that the hard way, when its wildly popular tyrant Peisistratos was succeeded by his sons.
After Peisistratos died in 527 BC, his sons Hippias and Hipparchus succeeded him as co-tyrants. At first, the siblings governed Athens competently and with a light hand. Then Hipparchus was assassinated in 514 BC in a private feud stemming from a romance that went bad. After his brother’s assassination, Hippias grew paranoid, and his rule became oppressive as he lashed out indiscriminately at enemies real and imagined. As Hippias grew ever more violent, and the number of victims and exiles forced to flee Athens grew, the popularity that tyranny had enjoyed since the days of Peisistratos faded.