It’s been over a year since information provided by NSA whistleblower Edward Snowden appeared in the Guardian and the Washington Post, illuminating again the fundamental tension in our national life between security provided by a government and civil liberties guaranteed by a constitution. Wiretapping has been a tool of law enforcement since the 1890s but it took until 1928 and a case before the Supreme Court to establish its constitutionality. The target of the wiretap was Roy Olmstead, the preeminent rumrunner in the Pacific Northwest, “the good bootlegger”: a former policeman, a businessman, a moralist and, by the laws of the day, a criminal. In “Roy Olmstead, A Rumrunning King on Puget Sound,” Norman H. Clark documents Olmstead’s career and the investigation by agents of the Treasury Department determined to arrest him. Wiretaps were then illegal in the State of Washington but were employed by federal agents in pursuit of their case. Olmstead was arrested and convicted largely on the basis of evidence provided by the eavesdropping. He appealed in circuit court but lost. A judge named Frank H. Rudkin wrote a prescient dissenting opinion which included the following: “I think it is also a matter of common knowledge that there is a growing tendency to encroach upon and to ignore constitutional rights. For this, there is no excuse… Must the millions of people who use the telephone every day for lawful purposes have their messages…intercepted? Must their personal, private, and confidential communications to family, friends, and business associates pass through any such scrutiny on the part of agents, in whose selection they have no choice, and for the faithful performance of whose duties they have no security?”