This chapter examines the enigmatic case of Charles H. Cooley and his placement in the sociological canon. During his lifetime, Cooley offered unprecedented theoretical insights, comparable in quality to famous concepts by other major social theorists. However, Cooley’s theory and legacy have not received the attention they deserve. Based on archival research and interpretive analysis, we discuss the enigmas surrounding Cooley’s legacy in sociology. Our main argument is that, whereas Cooley is an author who has achieved relative recognition as a classic, he has not benefitted from the proper theoretical involvement associated with this status. We discuss several reasons for this: Cooley’s unique theoretical writing; the reputational dynamics affecting his work; and the academic recognition logics involved in citations.