Part I details the conventional paradigms of criminal and civil law. Part II conceptualizes the parameters of the middleground, mainly focusing on state-invoked, punitive civil monetary sanctions. A main theme of this material is the U.S. Supreme Court's use of legal fictions in describing punitive civil sanctions to avoid the procedural implications of punitiveness, particularly the creation of high procedural barriers to imposing sanctions. Part III focuses on the causes of the accelerating growth of punitive civil sanctions. The causes are complex and include the growing influence of utilitarianism and deterrence theory in the law, the general expansion of law and litigation, the increasing authority of administrative agencies, frustration with the procedural obstacles of the criminal law, and reforms in civil procedure. Part IV discusses the implications of middleground jurisprudence. The author suggests increasing both the size and frequency of punitive civil monetary sanctions, so as to decrease the use of criminal law. He also argues that the procedure with which punitive civil sanctions are imposed fails to protect substantive and procedural due process values and that the future use of such sanctions, should they grow in size, may subvert these values if no independent middleground procedure is developed. 288 footnotes