The Anatomy of Error: Ancient Military Disasters and Their Lessons for Modern Strategists by Barry Strauss and Josiah Ober.
Read this book. It's out of print but shouldn't be too difficult to find.
I have begun (if not necessarily posted) dozens of pieces for De Spectaculis based upon the frame Strauss and Ober offer, but I have never specifically addressed their work. It is selfish of me to have kept this gem to myself. Of course, wisdom is seldom accompanied by happiness.
From the Introduction:
Chapter 1 shows the problems that arise when policy is a direct product of an imperial ideology and political leader's sense of personal legitimacy becomes involved in strategic planning. In Chapter 2, we investigate the suicidal policy that resulted when a charismatic general played upon a democratic society's vision of its own greatness. Chapter 3 considers the irony of an elite that was so thoroughly indoctrinated in the myth of its own military invincibility that it fell victim to its own self-deception and propaganda. [...] In Chapter 5 we asses what happens when a tactically brilliant general who loves to fight builds a strategy on a falsely optimistic view of the instability of the enemy's [...] system. Chapter 6 concerns the terrible social toll exacted from a state that allows its policy and strategy alike to become enmeshed in the selfish political ambitions of a narrow ruling clique. In Chapter 7 a politician's use of image projection, cultural myth manipulation, and negative propaganda lead to the fall of a masterful field commander. Image leads to error again in Chapter 8, in which an emperor launches a war to enhance his image with his own subjects and loses it because of a disastrous delusion of his own grandeur.Posted by MartialIn each case study, we see a failure by policymakers and strategists to know themselves, to know their enemies, or both. In none of the cases is the lack of knowledge just a psychological quirk - as we stated at the outset, this is not a study of born losers. To know oneself is to look outward as well as inward. Each of the failures presented here resulted from someone's or some group's fatal misapprehension regarding the natures and needs of (at least) one of the societies involved in the conflict. It is in the field of the policymaker's vision of social and political reality that the most dangerous strategic errors lie.