This Article will explore several themes. Primarily, this Article analyzes the psychologies of both an accused and the police as both interact with and battle each other psychologically over the possibility of a confession. The above analysis occurs through the prism of Fyodor Dostoevsky’s famous 1866 work Crime and Punishment. Specifically, a literary analysis of two key characters appearing in Dostoevsky’s book will be utilized in this Article. The actions of the two key characters analyzed involve “Raskolnikov,” an individual suspected of committing a double‐homicide, and “Porfiry,” the chief police detective charged with investigating the crime. Through an analysis of the actions of Raskolnikov and Porfiry, and how the two interact with each other, this Article raises and attempts to address important points regarding a defendant’s impulse to confess to his or her actions. This Article also analyzes the actions of a trained detective, Porfiry, and the strategies the detective employs to elicit a confession from the suspect, Raskolnikov. As a secondary theme, again through the prism of analyzing these two characters in Crime and Punishment, the author draws several conclusions about the importance of legal representation in order to protect defendants and help avoid damaging confessions elicited by savvy police tactics. As described by Dostoevsky in the book itself, there is a particular “psychology of a criminal before and after the crime” and the police “have a psychology of their own” in dealing with those suspected of crimes. These psychologies are analyzed in this article. This Article falls within the Law & Literature genre—that is articles which utilize classical works of literature to illustrate various principles of law and the legal profession.