Gambling provided the most common and ubiquitous means by which Renaissance Italians confronted the risks and the potential of the unknown future. This chapter examines how in the mid-sixteenth century, a small group of authors used their familiarity with games of chance to present themselves as experts in futurity. It argues that they presented the confrontation with the future provided by gambling as a test of character. The ability to master the anxiety provoked by uncertainty and to control one’s emotions in the face of both victory and defeat, they argued, represented an essential attribute for navigating society. Gambling, this chapter demonstrates, provided a sentimental education for life in sixteenth-century Italy: a society built on financial risk taking, and a culture adapting to a new conception of the future as unknown.