Pleading Guilty is closely related to all of Turow's earlier works. As in One L (1977), this novel explores the moral and ethical dilemmas posed by legal practice. It shares with Presumed Innocent and The Burden of Proof (1990) a concern with the darker sides of human experience and their impact on people's relationships. Further, once again, Sandy Stern puts in a brief appearance as the lawyer who defended Malloy's former partner. Turow's fictions increasingly seem to ask whether anyone can be presumed innocent.

Further, if people are always guilty for one reason or another, how can our legal system cope with this type of corruption?