Makers of Ancient Strategy: from the Persian Wars to the Fall of Rome
edited by Victor Davis Hanson
Princeton University Press
available in printed and ebook format (though there's not the price break there should be for the ebook version considering it has no material costs)
I just finished reading the ten essays in this book edited by Dr. Hanson.
The majority of the essays not only cover their classical antiquity subject but attempt to relate the subject matter to modern society and warfare. I highly recommend it.
Pericles, Thucydides, and the Defense of Empire, by Donald Kagan
Points out that the growth of the Athenian empire was due in part to the fact that other participating city states preferred to send money to Athens to develop weapons and mount armies rather than develop their own weapons and send their own men to fight. Then they complained about the growing Athenian dominance and that they had less and less say in the direction the confederation took. Parallels to European dependence on the U.S. for defense.
Epaminondas the Theban and the Doctrine of Preemptive War, by Victor Davis Hanson
After being attacked by Sparta again and again in previous warring, Thebes struck first at Sparta’s homeland to avert further attacks. They also tried to set up new democratic city states to surround Sparta with democracies (e.g., Manitineia, Megalopolis and Messene). It didn't work out so well. Parallels to nation/democracy building in Iraq.
Alexander the Great, Nation Building, and the Creation and Maintenance of Empire, by Ian Worthington
Alexander kept expanding his empire to include very diverse peoples and cultures. He tried some strategies to solidify his empire, but holding it together was a secondary concern to continuing expansion. Results: the break up of the empire after his death.
Urban Warfare in the Classical Greek World, by John W. I. Lee
Traces the use of walls both to keep enemies out or to trap and confuse them when they got in. Parallels to urban warfare in Iraq.
Slave Wars of Greece and Rome, by Barry Strauss
Good overview of the strengths and weaknesses in slave revolts of the time.