Developing the arguments of Chapter 1, this chapter examines the everyday experiences and policing of gambling in Italy during the fifteenth and sixteenth centuries. It traces shifting attitudes toward games of chance in both penitential thought and civil regulation. It argues that civil law attitudes toward gambling were structured by the notions of honor and social status held by the homosocial office-holding classes of Italian cities. While these governors understood themselves to possess the requisite social and financial capital to gamble, they continually attempted to restrict the ability of women, younger men, and lower socioeconomic estates to play at games of chance. The chapter also uses artworks and criminal prosecutions to trace resistance to this attitude by the excluded, revealing that the notions of honor, character, and self-control that pervaded elite ideas about gambling penetrated deeply in Italian society, although manifesting in different ways. In both cases, attitudes rested on ideas about what it meant to take chances on the unknowability of the future.