The second chapter focuses on the tale of Calandrino and the heliotrope (8.3). It asks two primary questions: why does Calandrino need to be a real historical person and what is the role of the custom agents in the tale? The answers to these questions are related because Boccaccio’s documentary style turns the pranks against Calandrino into a form of community policing. The shaming of Calandrino is a group effort and a public spectacle, a form of pittura infamante. In a justice system in which art could function as social conditioning by making citizens feel continually seen, it makes all the difference whether the person depicted can be identified. The tale of Calandrino and the heliotrope is justly celebrated as a masterful reflection on art and illusion. This chapter illustrates the political nature of this reflection. Namely, is Calandrino simply a bad friend—or is he also a bad citizen? Contemporary readers would thus have understood the real threat posed by Calandrino’s illegal—and supposedly undetected—border crossing when he passes through the gates without paying the custom agents. At stake is why we should obey the law when there is no one around to see.