This chapter provides a cultural history of the wicked advocate from the tenth to the nineteenth centuries in order to argue that advocates’ corrupt practices of justice and protection reflect deep-rooted problems in the history of local administration. It starts with monasteries’ miracle stories about advocates suffering in death as punishment for their crimes in this life. It then turns to the Swiss legend of William Tell and analyzes the earliest versions of the legend in order to demonstrate that Tell’s rival, the wicked advocate Gessler, abused his position in ways similar to those of other advocates. This chapter then discusses Friedrich Schiller’s play Wilhelm Tell to show that concerns about corrupt practices of justice and protection extended into the early nineteenth century. Local legends about bad advocates, some of them preserved today on the Internet, provide additional evidence for the enduring value of stories about wicked advocates who are punished for their bad deeds.