Olmstead (like Joseph Kennedy Sr.) ran a huge bootlegging business during Prohibition, employing 50-75 individuals, and delivering vast quantities of Canadian alcohol to American consumers from his headquarters in the State of Washington. His only mistake was that he failed to take into account an ingenious new federal intrusion into the people's privacy, the wiretap, which, in its capacity as a "law enforcement tool" was a relatively new technology at that time. He should not have had to worry, because wiretaps were illegal in Washington State.

Like a group of drunken actors cavorting on a stage, not realizing that an audience had filtered in, Olmstead and company put on a highly entertaining performance for an entire team of federal eavedroppers and stenographers, who, ignoring the Washington statute, proceeded to record 775 pages of telephone liquor deals, and to carry the transcripts thereof into federal court where they obtained a conviction against Olmstead.

His attorneys were apparently incredulous that the wiretap transcripts were admitted, being, as they obviously were, a form of illegal search and seizure, barred by the 4th Amendment. They appealed to the Supreme Court, where, by a slim 5-4 majority, with a most emphatically stated dissenting opinion, the wire-tap was upheld.

Among the dissenting opinions expressed, none was as chilling as that of Justice Louis Brandeis, who stated, most prophetically:

"The progress of science in furnishing the government with means of espionage is not likely to stop with wire-tapping. Ways may some day be developed by which the government, without removing papers from secret drawers, can reproduce them in court, and by which it will be enabled to expose to a jury the most intimate occurrences of the home. Advances in the psychic and related sciences may bring means of exploring unexpressed beliefs, thoughts and emotions. 'That places the liberty of every man in the hands of every petty officer,' was said by James Otis of much lesser intrusions than these.'"