The Greek Tyrants by A. Andrewes

I've had this Harper Torchbook edition for a ridiculously long time, and it's a book I've seen on my shelf and challenged myself to read many times, to no result. No biographical data on Mr. Andrewes is provided, but it's no surprise to find on Wikipedia that he was, as I imagined him, an Oxford classicist of the old school (the first edition of The Greek Tyrants was published in 1956).

Although short and incredibly dry, this volume packs a lot of information as to what was known about pre-classical political structures of ancient Greece, and particularly about the long transitional period from the "dark ages" from monarchy to aristocratic rule, and subsequently from tyranny (in the instances where it occurs) to democracy.  Sources from this time are scarce, and it is the work of contemporary poets, such as Hesiod and Pindar, that supplement the (often questionable) writings concerning various tyrannies in later historians such as Herodotus. Although some archeological evidence is referenced, anecdotes and quasi-legendary stories make up a good deal of the "facts", such as this amusing story:

Something must also be said of the spectacular meeting about 570 which ended in the marriage of Cleisthenes' daughter Agariste to the Athenian Megacles, the son on Alcmeon.  Herodotus tells us about this competition organized in the leisurely style of the epic.  A formal invitation was proclaimed at Olympia after Cleisthenes' victory in the games, the illustrious suitors spent a year in various tests at his court, then on the last evening the dance of the Athenian Hippocleides grew wilder till at last he stood on his head and waggled his legs: Cleisthenes warned him that he had danced away his marriage, but he replied "Hippocleides doesn't care."

Most other anecdotes are more brutal, such as the tyrant of a Greek colony in Sicily who was famous for roasting his enemies inside a large bronze bull, and battlefield atrocities are not uncommon. There is a good discussion of the Samian tyrant Polycrates, who was - depending upon who you asked - either a pirate or a shrewd operator who understood the value of sea power.  He must have had charisma: Herodotus notes that "his friends were more pleased when he returned their goods than if he had never seized them in the first place."

Andrewes is not one to overpack his study with anecdotes however, and we read insightful analyses of the role of the growing middle class in providing hoplites to tyrants as a hedge against aristocratic overreach, the political status of the Sicilian colonies and the Greek enclaves along the coast of Asia Minor, the development of the unique Spartan system, and the growing shadow of the Persian Empire and its influence on Greece through support or dissatisfaction of various tyrants along the western seaboard. Andrewes begins the study with a long analysis of the etymology and meaning of the word "tyrant" (tyrannos) itself, noting that the term carried a variety of connotations in ancient writers: that tyranny in pre-classical Greece was necessarily considered bad should not be assumed. Much depends on the author and the context to which he is referring.