This chapter examines pragmatism by focusing on two writers who rely on chance to conduct their investigations: Charles Sanders Peirce and Anna Katharine Green. It looks at Green's detective fiction (including The Woman in the Alcove) in relation to Peirce's account of his own sleuthing after a stolen watch (“Guessing”) and shows that both writers had difficulty reconciling a socializing conception of chance with narrative forms that are, by definition, highly teleological. The chapter first traces the development of Peirce's conception of absolute chance out of his earlier and more cautious claims about probability theory and pragmatic contingency, along with his gradual transition from pragmatism in the 1870s to a more traditional metaphysics later. It then considers Green's chance-saturated fiction which, like that of Peirce, encounters the problem of representing chance in a genre destined to demystify crime in the end. The chapter concludes by looking at a third detective writer interested in chance, Edgar Allan Poe.