This study attempts to connect two of the most important legal themes: guilt and punishment, by examining them in general terms and through their reflection in world literature. In particular, it explores the works of three authors who excel in these issues: Miguel de Cervantes, Fyodor Dostoyevsky, and Franz Kafka. The topic of guilt and punishment is studied both from an abstract perspective and in its application to the lives and writings of these three distinguished figures in literary history. The first two chapters establish a rich theoretical framework from a variety of perspectives – psychological, religious, juridical. The following chapters take the reader on a fascinating journey through 2,500 years of world literature, from Aeschylus to John Grisham. This back-and-forth between speculative and literary approaches is one of the main strengths of the book. These are just some of the many issues that the author lucidly and insightfully addresses in this captivating new monographic work, which is complemented by an extensive bibliography on the subject.