Examines the role of the unexpected, discussing why improbable events are not anticipated or understood properly, and how humans rationalize the black swan phenomenon to make it appear less random

• Prologue
• Umberto Eco's antilibrary, or how we seek validation. The apprenticeship of an empirical skeptic ; Yevgenia's black swan ; The speculator and the prostitute ; One thousand and one days, or how not to be a sucker ; Confirmation shmonfirmation! ; The narrative fallacy ; Living in the antechamber of hope ; Giacomo Casanova's unfailing luck : the problem of silent evidence ; The Ludic fallacy, or the uncertainty of the nerd
• We just can't predict. The scandal of prediction ; How to look for bird poop ; Epistemocracy, a dream ; Appelles the Painter, or what do you do if you cannot predict?
• Those gray swans of Extremistan. From Mediocristan to Extremistan and back ; The bell curve, that great intellectual fraud ; The aesthetics of randomness ; Locke's madmen, or bell curves in the wrong places ; The uncertainty of the phony
• The end. Half and half, or how to get even with the black swan
• Epilogue : Yevgenia's white swans
• Postscript essay: on robustness an fragility, deeper philosophical and empirical reflections. Learning from mother nature, the oldest and the wisest ; Why I do all this walking, or how systems become fragile ; Margaritas ante porcos ; Asperger and the ontological black swan ; (Perhaps) the most useful problem in the history of modern philosophy ; Fourth quadrant, the solution to that most useful of problems ; What to do with the fourth quadrant ; Ten principles for a black-swan-robust society ; Amor fati: how to become indestructible