The chapter “Spanishing the Pícaro” discusses the people with whom the pícaro relates. It discusses the referentiality of the literary “associations of rogues” in the texts of Mateo Alemán, Liñán y Verdugo, Carlos García and Cervantes. It challenges the central notion in current interpretations of literary representation of criminal associations in the picaresque novel that the typologies of outlaws (way layers, burglars, pimps)—a common motif of the picaresque—were intended to criticize the professional guilds of their time. Pleas from Madrid constables, inventories of criminal cases and trial records represent the rogues as highly specialized and effective at employing cross-cultural networks. Moreover, the extraliterary gangs were highly heterogeneous; in early modern Madrid there were Greeks, Armenians, Bulgarians and Turks who collaborated with each other, and with Castilians and city officials in intricate criminal schemes for several decades before being apprehended. Strikingly, the diversity of the urban underground that can be found in the institutional sources is all but absent in the literary associations of rogues. This points towards a homogenizing of the urban outlaw in the literary representations, a de facto “Spanishing” of the rogue.