The invention of probability emerged out of a recognition of uncertainty linked to a theological belief system and an account which allowed a rational glimpse of the future; mathematical probability in turn arose out of the recognition of the random fall of the dice and the understanding of equiprobability by Cardano (1501–1576). So, the narrative probability already existed before the first rudiments of the mathematical were found. This is the main finding offered in this chapter. The early intuition of risk, based on the narration of a probability, in the seventh century and the emergence of the probability calculus in the sixteenth century share a way of looking at the future, and in both cases we find that the approach begins by limiting possibility, in one case by describing God’s providence as an assurance of success and a source of confidence in the outcome, and in the other by setting bounds on the event and then splitting it up to allow calculation. Two ways of conceiving probability, and ultimately risk, sharing a common epistemology, were constructed and related historically, first as narrative and then as calculus.