Gambling with Philosophy weaves together philosophy and gambling to illustrate how chance is intimately involved in every part of our lives. It does this by crafting a story where a career in philosophy and an interest in gambling both come about through chance occurrences. The emphasis on chance as a natural random part of the world is contrasted with the common reference to "luck" as a metaphysical force that for some unknown mystical reason rewards the "lucky" few, and hurts the "unlucky" majority of humans. A series of conversations reveals how games of chance and the chance occurrences that occur throughout life present us with gambles involving uncertainties, the outcomes of which determine the course of our lives.