This text discusses how the characterization of Saul shows that kingship failed, why it did, and how the institution would need to be ended. It marries the following elements: a given text (1 Samuel), a focal character (King Saul), a spacious and creative theorist (Mikhail Bakhtin) and a historical context (the collapse of monarchic Israel and the moment for return. The dilemma for the exile community is to return with royal leadership or without it). The text poses the question of whether a character can be a cipher for a corporate experience - does Saul represent the whole monarchic experience? The thesis of the work is that Israel's first king is authored in such a way that the narrative of 1 Samuel may be read as a riddle propounding the complex story of Israel/Judah's experience with kings as an instruction for those pondering leadership choices in the sixth century. The work is an extended reflection on what went wrong with kings and why new leadership must be attempted.The extended riddle of Saul works to show how the life of the king is fundamentally destructive, not because he is malicious, but because of many factors of weakness and inadequacy that should be familiar to readers.