Crucially, the Prison Shakespeare field of research has become an exciting hub for discussion about a presumed intrinsic virtuosity of Shakespeare plays against the background of what might best be termed as “new character criticism” in Shakespeare studies as well as a battlefield between the supporters and the opponents of prisons as effective in achieving their stated objective of keeping society safe. This discussion has profoundly influenced and continues to influence the different trends of thought about the quality of the “transformation” Shakespeare carries out in prison. Can Shakespeare’s theatre be regarded as a salvific one when most of the characters in his plays are villains? The chapter focuses on Italian director and actor Armando Punzo’s pioneeristic practice of theatre in prison and his interpretation of “transformation” in an extra-moral sense.