Nearly a century before a U.S. President accused his predecessor of ordering a tapp on his private telephone line, and before he tweeted a warning to the head of the F.B.I. that he had better hope that there are no tapes of our conversations, a professional spy, armed with a pack of cigarettes and an earpiece, hid in the basement of the Henry Building, in downtown Seattle, catching crackling bits of words being spoken miles away. Richard Fryant had worked as a wiretapper for the New York Telephone Company, tasked with eavesdropping on his own colleagues, and now took freelance assignments in the Queen City. On this occasion, he was seeking dirt on Seattles corrupt mayorwho was suspected of having ties to Roy Olmstead, a local bootleggerfor a political rival. At the behest of his client, Fryant rigged micro-wires to a certain exchange, ELliott-6785, and began to listen.

They got that load, one man said, breathing heavily.

The hell they didwho? asked another.

The federals.

The men speaking on ELliott-6785 hung up, but the conversation had only just begun.

Criminals and Prohibition officials alike called Olmstead the good bootlegger, a moniker that reflected his singular business philosophy. He never diluted his whiskey with water or corrupted it with poison; he declined to dabble in the seedier offshoots of his profession, such as drugs or prostitution; and he abhorred violence, forbidding members of his organization from carrying weapons (No amount of money is worth a human life, he cautioned). If apprehended, his men were instructed to rely on bribes instead of violence.

Olmstead had a particular respect for policemen, having been a member of the Seattle force for thirteen years, reaching the rank of lieutenant. In 1920, with the onset of Prohibition, the thirty-three-year-old married father of two ventured to the other side of the law, making midnight runs to retrieve imported Canadian liquor from tugboats in the Puget Sound. This practice earned his dismissal from the force and made him a local celebrity. With his old police colleagues on his payroll, he was free to conduct business brazenly and with impunity, often unloading his booze at high noon from trucks marked Fresh Fish. Seattle citizens were thrilled to glimpse Olmstead on the street, wearing a fine suit and carrying a wallet fat with money, always ready with a joke. As one acquaintance noted, It made a man feel important to casually remark, As Roy Olmstead was telling me today.

Olmsteads organization, comprised of an ever-growing staff of attorneys, dispatchers, clerks, skippers, navigators, bottlers, loaders, drivers, deliverymen, collectors, and salesmen, dominated the bootlegging scene in the Pacific Northwest. They relied heavily upon the telephone for day-to-day operations, using it to take orders, communicate updates on deliveries, and warn of impending raids, their words coursing across a web of wires connecting the citys fifty-two thousand devices (approximately one for every six citizens). Olmstead set up his communication headquarters in the Henry Building, just a block from the Federal Building, and established three exchanges: ELliott 6785, 6786, and 6787. One of his men, a former taxi dispatcher, sat during business hours at a roll-top desk, taking and making calls, keeping meticulous records of each transaction. If a serious matter arose, such as an employees arrest, Olmstead himself called a friend on the Seattle police force to have it quashed. At the end of each day, the dispatcher unplugged the three telephones, to stop their ceaseless ringing, and the routine began anew in the morning.

In early 1924, Olmstead was approached by Richard Fryant, the freelance wiretapper who had been hunkered down in the basement of the Henry Building, listening to Olmsteads lines. As the bootlegger would soon learn, Seattles Prohibition Director, William Whitney, had heard of Fryants surveillance and recruited him as a federal agent.

In Olmsteads version of events, Fryant presented him with a heavy stack of paper, explaining that the pages contained verbatim transcripts of conversations that had been conducted on the bootleggers office phone. For ten thousand dollars, Fryant said, the transcripts could be his. A quick perusal of the pages confirmed their authenticity.

A call from a cop to a worker at Olmsteads headquarters:

Down under the Fourth Avenue Bridge is a car with seven gallons of moonshine in it, and I was wondering if it is yours.

No . . . I dont think it is ours because we dont handle moonshine.

A call from Olmstead to the police station:

Hello, Roy, what is on your mind?

One of your fellows picked up one of my boys. . . . I dont give a damn what they do but I want to know before he is booked.

Ill take care of it for you, Roy.

A joking exchange between Olmstead and a dispatcher:

The federals will get you one of these days.

No, those sons of bitches are too slow to catch cold, Olmstead quipped,

Reading the pages, Olmstead maintained his composure. As a former police officer, he said, when hed finished reading, he knew a thing or two about the rules of evidence. Wiretapping was illegal in the state of Washington, so the pile of paper would be useless in a courtroom. Furthermore, Fryant could go straight to hell.

Olmsteads bravado did not prevent him from hiring a telephone repairman to search the Henry Building first thing in the morning. Together, they found and removed three temporary taps (affixed with coil wire rather than soldered)two in the basement and one in the womens restroom. Still unsettled, Olmstead returned the following day and discovered that all three taps were back.

Fryant and Whitneys wife, Clara, a skilled stenographer, continued to monitor ELliott-6785 from an office one floor below. At each days end, Clara gathered up the handwritten notes and typed them with fastidious precision. The pile of paper continued to grow.

For the first time in his bootlegger career, Olmstead started exercising some discretion about his wordsbut only some, because he still trusted that Fryants wiretapping evidence would never withstand legal scrutiny. When managing the arrival of his whiskey boats in Puget Sound, he used a public pay phone to issue instructions and directions. For less sensitive issues, he continued to use his office line, and even had fun at the wiretappers expense, calling Whitney profane names and giving false orders about the timing and location of deliveries. It amused him to imagine the Prohibition chief sitting alone in the freezing rain, grasping his gun and waiting for boats that would never come.

Whitneys patience paid off in October, 1924, when Canadian officials seized one of Olmsteads boats. Three months later, a federal grand jury returned an indictment against Olmstead and ninety co-defendants for conspiracy to violate the National Prohibition Act. The Whispering Wires case, as it came to be called, concluded with a guilty verdict, a fine of eight thousand dollars, and a sentence of four years hard labor. Convinced that his Fourth and Fifth Amendment rights had been violated (the right against unreasonable searches and seizures and against self-incrimination, respectively), Olmstead put his lawyers to work on Olmstead v. The United States. The Circuit Court of Appeals upheld his conviction, maintaining that, because the federal agents wiretapping pursuits did not require them to trespass on Olmsteads property or confiscate physical possessions, there had been no breach of rights.

The Supreme Court heard Olmstead v. The United States in February, 1928, and, in a 54 decision, upheld Olmsteads conviction. Chief Justice William Howard Taft, speaking for the majority, recognized the murky morality of wiretapping. Nevertheless, he argued that the practice served a greater good. A standard which would forbid the reception of evidence if obtained by other than nice ethical conduct by government officials would make society suffer and give criminals greater immunity than has been known heretofore, he wrote. He rejected the heart of Olmsteads case, insisting that the Amendment does not forbid what was done here. There was no searching. There was no seizure. . . . 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.

The dissenting opinion was penned by Justice Louis Brandeis, for whom the issue of privacy was both ancient and increasingly, inescapably modern. In 1890, while practicing law in Boston, he had co-authored an article published by the Harvard Law Review titled The Right to Privacya manifesto, as Jill Lepore has written in this magazine, that argues for the existence of a legal right to be let alonea right that had never been defined before. Although the telephone was still decades away from being a familiar and necessary aspect of our lives, nearly every line of The Right to Privacy reveals prophetic insight into current concerns about how best to shield our innermost selves. The intensity and complexity of life have rendered necessary some retreat from the world, Brandeis wrote.

The Right to Privacy became a seminal work, and one that clearly influenced Brandeis himself as he considered Olmsteads case. When the Founding Fathers crafted the Constitution, he wrote in his dissent, the right to be left alone was inherent in the notion of pursuing happiness. To protect that right, every unjustifiable intrusion by the government upon the privacy of the individual, whatever the means employed, must be considered a violation of the Fourth Amendment. . . . If the government becomes a lawbreaker, it breeds contempt for the law.

The media, although invested in a world where sensitive information might be easily and readily obtained, largely favored Brandeiss view. The Times declared that the Olmstead decision allowed universal snooping. The New Haven Journal-Courier predicted that every Tom, Dick and Harry would hereafter practice wiretapping without fear of reprisal. The editors of the weekly magazine Outlook were even more blunt, likening the verdict to a new Dred Scott and predicting dire consequences: We must weather the devastating effects of a decision that outrages a peoples sense of a security which they thought they had.

Forty years later, the Supreme Court finally caught up with Justice Brandeis, refining the Olmstead decision in two separate cases. In June, 1967, Berger v. New York considered the appeal of Ralph Berger, a public-relations consultant who had been convicted of conspiracy to bribe the chairman of the New York State Liquor Authority. Under the authority of a New York statute, police wiretapped Bergers phone for two months, and played excerpts of their recordings during the trial. In a 63 decision, the Supreme Court ruled that the New York law was too broad in its sweepspecifically too long, as the two-month surveillance amounted to a series of intrusions, searches, and seizures that violated the defendants Fourth Amendment rights.

Six months later, the Supreme Court directly addressed the legacy of the Olmstead decision, in the case of Charles Katz, a California man convicted of placing illegal gambling wagers across state lines. Without a warrant, F.B.I. agents wiretapped public pay phones along Sunset Boulevard, hiding the device atop the bank of booths and listening in as Katz placed bets in Miami and Boston. The Court of Appeals upheld Katzs conviction, concluding that, since there had been no physical entrance, his privacy had not been compromised. In a 71 ruling, the Supreme Court reversed this decision, arguing that the Fourth Amendment protects people, not places, and that its reach cannot depend on the presence or absence of a physical intrusion into any given space. Citing Justice Brandeiss manifesto, the Court established the protection of a persons general right to privacy (emphasis the Courts) and his right to be let alone.

Olmstead served his four-year sentence. Yet, in a way, he managed to win his case. Victory came in the form of a Presidential pardon, granted by Franklin D. Roosevelt, on Christmas Eve of 1935, which restored all of his rights as a citizen and cancelled the fine. Roosevelt was influenced, in part, by Olmsteads nascent transformation: hed quit drinking, converted to Christian Science, and started teaching the Bible to prisoners, who frequently asked if he was really *that *Roy Olmstead, the good bootlegger, the rum-running king of Puget Sound. His standard replyNo, not any more. The old Olmstead is deadamounted to fewer than a hundred and forty characters, and were the words he wished the whole world to hear.

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The Bootlegger, the Wiretap, and the Beginning of Privacy - The New Yorker