Meet Roy Olmstead and Charles Katz—one was a Prohibition era bootlegger, the other a '60s gambler. Neither did anything earthshaking with their lives, but history remembers them both because their arrests, based on warrantless telephone taps, reached the United States Supreme Court.

In the two cases that resulted, the Supremes took starkly different perspectives on whether the men's constitutional rights had been violated by wiretaps without a warrant.

"The right of the people to be secure in their persons, houses, papers, and effects, against unreasonable searches and seizures, shall not be violated," says the Fourth Amendment. But as telephone wires invaded the 20th century, judges had to constantly rethink what that sentence meant. In doing so, the justices paved the way for modern wiretap law and for the controversies over warrantless wiretapping that would become a feature of the "War on Terror."

A training ground

In 1925, Prohibition was the law of the land. The Volstead Act banned the sale of intoxicating beverages throughout the United States—defined as those containing more than "1 per centum or more of alcohol by volume." Protestant churches across the land rang their bells at the news of the law's enactment. President Hoover called it a "noble experiment."

But the legislation contained a glaring flaw. Congress allocated very little money to the Act's enforcement. This meant that Prohibition Agents often made less salary than garbage collectors, and were thus extremely susceptible to corruption. One bitter Volstead administrator later called the Prohibition Bureau "a training ground for bootleggers." This was because of "the frequency with which agents left the service to sell their expert knowledge to their old enemies," as a historian of the period later wrote.

One of these turncoats was Roy Olmstead, a former police lieutenant, soon doing brisk business as a liquor dealer in Seattle, Washington. Today, Mr. Olmstead is celebrated by Washington historians as the "King of Puget Sound" bootleggers. He was also one of the area's biggest employers, hiring great numbers of salesmen, delivery staff, dispatchers, bookkeepers, and of course, an attorney.

His workers stored illegal spirits in a ranch outside of town and in various hideaways around the city. But it wasn't a terribly covert operation. Olmstead did his selling via an office headquarters downtown. His associates and clients could call no less than six telephone numbers to contact the operation.

The remaining honest federal agents in Seattle took note of these lines. They placed wiretaps in the basement of Olmstead's offices and in phone installations near the homes of various Olmstead employees. For months they listened in on sales transactions and to the bribing of their colleagues.

Finally, the authorities arrested 90 people. These included Olmstead, his wife, and his attorney. 21 were eventually convicted of breaking Prohibition laws, and of profiting handsomely from doing so.

"In a bad month sales amounted to $176,000; the aggregate for a year must have exceeded two millions of dollars," one judge disapprovingly observed.

Not surprisingly, given the size of the case, it was sent up to the Ninth Circuit Court of Appeals, which in 1927 upheld the convictions. But Justice Frank H. Rudkin dissented. The government had obtained no warrants for the wiretaps used in the case, he protested, as it surely would for a writ to read postal mail.

"What is the distinction between a message sent by letter and a message sent by telegraph or by telephone?" Rudkin asked.

True, the one is visible, the other invisible; the one is tangible, the other intangible; the one is sealed, and the other unsealed; but these are distinctions without a difference. A person using the telegraph or telephone is not broadcasting to the world. His conversation is sealed from the public as completely as the nature of the instrumentalities employed will permit, and no federal officer or federal agent has a right to take his message from the wires, in order that it may be used against him. Such a situation would be deplorable and intolerable, to say the least. Must the millions of people who use the telephone every day for lawful purposes have their messages interrupted and intercepted in this way?

He concluded that, "if ills such as these must be borne, our forefathers signally failed in their desire to ordain and establish a government to secure the blessings of liberty to themselves and their posterity."

With this dissent in hand, the Olmstead case went to the Supreme Court. There, the majority took a very different perspective on the matter, with their opinion delivered by a former President of the United States.

An enlarged and unusual meaning

Republican William Howard Taft had first come to national prominence when William McKinley appointed him Governor of the Philippines following its brutal occupation by the US in 1901. From this position he moved to Secretary of War, then became Theodore Roosevelt's Vice President, and finally took the job of President in 1908.

Then Taft sank in the tightly contested Presidential race of 1912, the victory going to Democrat Woodrow Wilson. But Wilson's GOP successor, Warren G. Harding, tapped Taft to become the Supreme Court's Chief Justice, where he remained until his death in 1930.

Given his formative background, it is not surprising that Taft viewed Rudkin's civil liberties perspective with skepticism. He was fine with warrantless wiretaps... because the wires left the home, and the Fourth Amendment applied only to homes and people. Having a telephone was a bit like being a broadcaster.

"The courts may not adopt such a policy by attributing an enlarged and unusual meaning to the Fourth Amendment," Taft's 1928 majority opinion explained. "The reasonable view is that one who installs in his house a telephone instrument with connecting wires intends to project his voice to those quite outside, and that the wires beyond his house and messages while passing over them are not within the protection of the Fourth Amendment. Here those who intercepted the projected voices were not in the house of either party to the conversation."

Since the police did not invade the personal premises of the defendants, the Fourth Amendment did not prohibit their warrantless actions. "There was no searching. There was no seizure," Taft noted. "The evidence was secured by the use of the sense of hearing and that only. There was no entry of the houses or offices of the defendants."

By the invention of the telephone, fifty years ago, and its application for the purpose of extending communications, one can talk with another at a far distant place. The language of the Amendment can not be extended and expanded to include telephone wires reaching to the whole world from the defendant's house or office. The intervening wires are not part of his house or office any more than are the highways along which they are stretched.

Again, the ruling came with a strong dissent—this time from Justice Louis Brandeis. The purpose of the Fourth and Fifth Amendments was not to define physical space, Brandeis insisted, but to define the rights of individuals.

When these principles were adopted, "force and violence were then the only means known to man by which a Government could directly effect self-incrimination," his dissent explained. "It could compel the individual to testify—a compulsion effected, if need be, by torture. It could secure possession of his papers and other articles incident to his private life— a seizure effected, if need be, by breaking and entry."

Now "subtler and more far-reaching means of invading privacy have become available to the Government," Brandeis observed. "Discovery and invention have made it possible for the Government, by means far more effective than stretching upon the rack, to obtain disclosure in court of what is whispered in the closet."

If the Constitution's amendments were living documents, then as technology changed, the parameters of these rights must change.

The makers of our Constitution undertook to secure conditions favorable to the pursuit of happiness. They recognized the significance of man's spiritual nature, of his feelings and of his intellect. They knew that only a part of the pain, pleasure and satisfactions of life are to be found in material things. They sought to protect Americans in their beliefs, their thoughts, their emotions and their sensations. They conferred, as against the Government, the right to be let alone—the most comprehensive of rights and the right most valued by civilized men.

To defend that right, "every unjustifiable intrusion by the Government upon the privacy of the individual, whatever the means employed, must be deemed a violation of the Fourth Amendment," Brandeis insisted.

But his was a minority perspective in 1928. Olmstead vs. United States, the right of police to tap electronic communications without warrants, became common law.

That is, until gambler Charles Katz was arrested in Los Angeles in 1965.