This work is aimed at the trouble with trying to learn about probability. A story of the misconceptions and difficulties civilization overcame in progressing toward probabilistic thinking. It is also an account of what makes the science of probalitity daunting in our own day. To acquire a (correct) intuition of chance is not easy to begin with, and moving from an intuitive sense to a formal notion of probability presents further problems. The author traces the path this process takes in an individual trying to come to grips with concepts of uncertainty and fairness, and also charts the parrallel path by which societies have developed ideas about chance. Why, from ancient to modern times have people resorted to chance in making decisions? Is a decision made by random choice fair? What role has gambling played in our understanding of chance? Why do some individuals and societies refuse to accept randomness at all? If understanding randomness is so important to probabilistic thinking, why do the experts disagree about what it really is? And why are our intuitions about chance almost always wrong? Anyone who has puzzled over a probability conundrum is struck by the paradoxes and counterintuitive results that occur at a relatively simple level. Why this should be, and how it has been the case through the ages, is the lesson of this book.