chapter Fifteen

The Case of the High-Tech Bootlegger

Olmstead v. United States (1928)

LAW BY ITS VERY NATURE always lags behind societal changes, and this is particularly true when it comes to technological development. A new technology challenges the courts to find already existing rules that can then be applied to new circumstances. In the nineteenth century, for example, it took many years before courts could establish rules regarding railroads and the liability they had for damages from steam engines spewing out sparks as they crossed farmlands. Sometimes years, even decades, pass before judges can articulate a workable rule that marries modern technology to constitutional safeguards.

In 1928 Justice Louis Brandeis tackled the question of a new technology—the telephone—and in doing so laid the basis for one of the most important constitutional developments of the twentieth century—the emergence of a right to privacy. Government agents had put a wiretap on the phones of a suspected bootlegger, gaining the information used to convict him of violating the Prohibition Act. On appeal he raised issues of what the Fourth Amendment required in terms of a search, and although he lost, Brandeis’s dissent would bear fruit over the next four decades until the Supreme Court adopted his reasoning and held that the Constitution did protect an individual’s right to privacy.

The Road to the Noble Experiment

Olmstead v. United States grew out of the great failed experiment of Prohibition, one of the legacies of the Progressive reform ferment that marked American society in the two decades leading up to the nation’s entry into World War I in 1917.

Americans always drank, and at least from colonial times there were those who viewed liquor as sinful. During the nineteenth and early twentieth centuries the prohibitionists won some notable victories, and by 1917 twenty-six states—more than half the Union—were legally dry—that is, they prohibited the manufacture, transportation, or sale of alcoholic beverages within their state borders. In addition, some of the so-called wet states permitted a local option allowing their rural areas to ban liquor. For those opposed to drink—and this included everything from beer to champagne to whiskey—all the problems of society resulted from drunkenness. The Anti-Saloon League claimed that each year, inebriated parents smothered some 3,000 infants in their cribs. Accidents on the job, broken families, husbands who deserted their wives, girls led to a life of debauchery—all arose from the same cause. Prohibitionists looked at a complex world through a single moral lens, and found liquor guilty of all they deemed wrong in America.

There were, of course, many problems confronting the United States in the early twentieth century. The great industrialization that had gathered steam after the Civil War reached its fruition around 1900, and the country was pockmarked by great factories spewing forth noxious gasses and employing thousands of workers. Many of those who toiled in the mills, mines, and plants had only recently arrived in the United States, part of the great wave of immigration from eastern and southern Europe between 1880 and 1920. What had been a nation of farms and small towns was rapidly transforming into a nation of cities, and by the 1920s the census would report that one-half of all Americans lived in urban areas. The cities, of course, with their more liberal attitudes on everything from politics to sex—and with a saloon allegedly on every corner—struck the rural Baptists and Methodists who made up the heart of the Prohibition movement as symbolic of all they believed wrong. Drink had sent God’s country staggering into the arms of Satan!

The rural dries, however, would not have been able to secure passage of Prohibition without the help of urban progressives and the war itself. Many reformers believed that if drink did not actually cause the evils they fought, it certainly contributed to it. Not all factory workers picked up their pay on Friday and then drank it away in the saloon, but a few did. Not all accidents in the mills and sweatshops could be attributed to workers drunk on the job, but some could. Not all husbands who deserted their families did so because of habitual drunkenness, but there were enough stories to give the charge credence.

Moreover, middle-class reformers detested the big-city political machines like Tammany Hall in New York that had their precinct offices in saloons and that rewarded faithful voters with free drinks. The forces that made these machines powerful from the 1880s to the 1930s had much to do with the great changes sweeping the nation and very little to do with alcohol, but the prohibitionists had a single moral lens that ignored everything but Demon Rum. They hated the cities and all the cities stood for, and in their eyes liquor epitomized the city.

During the war the necessity to conserve grain for food, both on the home front and for the troops, led Congress to adopt a wartime prohibition on the production of alcohol. In December 1917 Congress passed a constitutional amendment to ban the “manufacture, sale, or transportation of intoxicating liquors within, the importation thereof into, or the exportation thereof from the United States,” and gave both Congress and the states concurrent power to enforce the prohibition. By January 1919 thirty-six states had ratified the Eighteenth Amendment banning alcohol, and in October 1919 Congress, over President Woodrow Wilson’s veto, enacted the Volstead Act to extend wartime prohibition and to define alcoholic as one-half of 1 percent alcohol by volume, a definition that could include partially fermented apple juice. On January 17, 1920, Prohibition—the so-called “Noble Experiment”—began.

Prohibition in Practice

In the decade that followed, it appears that drinking in general amongst the population declined, especially in the rural areas that had most fervently supported the ban. As a whole there were probably fewer arrests in the country resulting from drunkenness and few deaths from alcoholism. According to a 1920 study undertaken by Survey magazine of Grand Rapids, Michigan, drunkenness had disappeared, families spent more time together, the saloon was no longer the visitor’s entry to the city, and the number of arrests for crime had dropped so much that the police force had been reduced—all as a result of Prohibition.

The study seems to have been overly optimistic, and may have reflected the support many people initially gave to Prohibition. It soon became apparent, however, that despite the ratification of the Eighteenth Amendment, many people in the country had little use for Prohibition. Even in rural areas, moonshine and hard cider abounded, while the cities were overwhelmingly opposed to the ban on drink. Before long, the Noble Experiment in social reform turned into a national nightmare of failed law enforcement and a widespread disdain for those agencies trying to enforce the ban.

Prior to 1919, Prohibition had been a state matter. The National Commission on Law Observance and Enforcement found state enforcement effective, while another study termed local law “fairly well obeyed and respected.” In contrast, federal enforcement of Prohibition quickly turned into a “nation-wide scandal” that, in President Harding’s words, was “the most demoralizing factor in our public life.”

At the heart of the problem lay the impossible task mandated by the Eighteenth Amendment, the moral reform of a nation that had been drinking since colonial times. Prohibition stands as the premier example of law’s inability to change the personal behavior of people who do not want to change. The amendment’s division of responsibility left it unclear who had the primary responsibility for enforcement—the states or the national government. Section 2 reads, “The Congress and the several States shall have concurrent power to enforce this article by appropriate legislation.” Did that mean that Congress could set up police functions inside the states? What if a state, such as Maryland, did not pass the necessary enforcement law or, as New York did in 1923, repeal its enforcement statute? Could states set up barricades to keep alcohol coming in from other states or from Canada? Who had the responsibility to patrol the shores to prevent smuggling? Did the federal government have the authority to conscript state law enforcement officers? The federalism that had been so essential a part of the American constitutional scheme for more than 130 years reeled from the onslaught of issues never imagined by the Framers of the Constitution.

The hastily thrown-together federal Prohibition agency (later the Bureau of Alcohol, Tobacco, and Firearms) lacked skilled personnel, and many of the “agents” were little more than political hacks, some of whom had criminal records, given their jobs by local bosses. They quickly aroused public resentment when they indiscriminately sprayed waterfront streets with bullets or invaded private houses without a search warrant. To many citizens, the agents seemed to be as lawless as the bootleggers they pursued.

Soon millions of Americans seemed to side with purveyors of illegal booze. On one occasion, thousands of weekend fun seekers at Coney Island in New York watched Coast Guard cutters chase rumrunners, and cheered as the latter opened a lead in escaping from the government boats. In Ocean City, Maryland, a mob of wets stormed the city jail to free two men arrested for drunkenness. In many big cities the agents seemed helpless. In New York, Chicago, or San Francisco, a stranger looking for a drink could stop a local policeman on the street who then politely pointed out the nearest speakeasy and also provided the magic words to get in—“Joe sent me.” In 1929 a former assistant attorney general in charge of Prohibition prosecutions conceded that liquor could be bought “at almost any hour of the day or night, either in rural districts, the smaller towns, or the cities.”

The American people, who prided themselves in their ingeniousness, came up with one device after another to get what the law said they could not have. Sophisticated chemical laboratories, hidden in warehouses, redistilled industrial alcohol (although the process, in less skilled hands, could yield products that poisoned, paralyzed, or killed thousands of people). Compliant druggists wrote prescriptions for alcohol that could then be blended with other ingredients. Many people brewed at home, and hardware stores openly displayed and sold the equipment needed. Boats smuggled in premium liquors from Europe and the Caribbean along New Jersey’s Rum Row, while ice sleds easily crossed over from Canada in midwinter.

The worst aspects of Prohibition were the big city gangs that not only overwhelmed law enforcement agencies, but usually corrupted local governments as well. In 1920 “Scarface” Al Capone, a petty hoodlum from the Five Points area of New York, moved to Chicago and quickly built an empire based on alcohol, gambling, and prostitution. By 1927 his businesses grossed more than $60 million a year, and his army of nearly a thousand thugs “took care” of rival bootleggers who tried to cut in on Capone’s territory. In 1926 and 1927 Chicago saw more than 130 gang murders, and police did not solve a single one of them.

In New York, Chicago, Philadelphia, and elsewhere, the real power in the city rested not with the elected municipal governments but with the gangs. As one commentator sarcastically noted, the gangs “eliminated waste, promoted efficiency, and replaced the disorder of obsolete individualism with rigorous discipline.” It was an ideal that advocates of the “New Capitalism” such as Herbert Hoover promoted during that decade.

The Olmstead Ring in Seattle

Criminals quickly adapted the new technologies of telephones and automobiles to help them circumvent Prohibition. In Seattle, a police lieutenant named Roy Olmstead learned all about the bootlegging business while making arrests, and realized that the main problem of running an illegal business was lack of organization. There were too many unconnected pieces, too many mistakes arising from lack of information and communication, and lack of leadership. Olmstead left the police department and proceeded to put together a highly efficient organization to import and distribute liquor in violation of the Volstead Act. The “Olmstead Ring” could have served as a case study at the Harvard Business School. Olmstead himself put in $10,000 for working capital and acted as general manager, while eleven others put in $1,000 each; 50 percent of the profits went to Olmstead, and the other partners divided the balance. At its peak, the organization employed between fifty and seventy people; it leased two seagoing vessels to bring the liquor from British Columbia to Seattle, and several smaller boats to distribute alcohol up and down the Washington State coast.

Olmstead purchased a ranch outside of Seattle with large underground facilities to store the imported cases, as well as several apartments in the city from which his men would make deliveries to local consumers. The ring ran out of a central office manned by telephone operators, salesmen, deliverymen, dispatchers, bookkeepers, collectors, and even an attorney. As a former police officer, Olmstead had contacts—including his two brothers—in the Seattle police department who kept him apprised of possible raids, and also helped him to arrange the release of any of his men who might be arrested.

From early morning to late at night, operators manned the telephone bank at the main office, and either Olmstead or one of his managers would then take the orders and give them to a deliveryman, who would go to one of the local caches, pick up the requested items, and take them to the customers. On some days the operation delivered as many as two hundred cases of liquor. As the court records showed, even in a bad month sales amounted to $176,000, and annual income easily topped $2 million (equivalent to more than $25 million in current dollars).

Little of this was secret. The local press dubbed Olmstead the “King of the Puget Sound Bootleggers,” and Olmstead made no effort to maintain a low public profile. In 1924 he divorced his first wife and married Elise Campbell, a vivacious young Englishwoman he met in Vancouver, Canada, while on a buying trip. He built her a beautiful mansion, which they dubbed the “snow white palace” in the exclusive Mount Baker neighborhood, overlooking Mount Rainier. The Olmsteads founded the American Radio Telephone Company, and brought in a young inventor, Alfred M. Hubbard, as a business partner. Together they built a large radio transmitter and one of Seattle’s first commercial broadcasting studios, KFQX. Federal law enforcement agents were suspicious of Olmstead’s real motives, and speculated that he used the station’s broadcast of children’s bedtime stories to send coded messages to his rum-running boats.

Federal agents utilized their own technology. They ran taps on the phones into the ring’s main office as well as the lines at Olmstead’s home and the residences of some of his partners. At the main office they set up a listening post table in the basement of the building, and attached earphones to the telephone wires using alligator clips. At the private residences they attached the wires either in the basements of apartment buildings, or on telephone poles outside houses. At no time did they enter the premises, nor did they have a warrant to eavesdrop—since neither police nor prosecution believed a warrant was necessary. One needed a warrant to enter a premise, but federal agents never actually did so; they listened from outside the office and the homes.

Over several months the federal agents came to know the bootleggers and their operations, and the difficulties they occasionally faced and overcame in their business. They learned the identities of the major customers, who the ring was paying off in the police department, and how Olmstead and his team responded when a ship was seized or storms delayed delivery. Over the course of the investigation the agents compiled 775 pages of transcriptions of telephone calls, and on that basis secured arrest warrants for Roy Olmstead and seventy other people. Some escaped, and at trial a few were acquitted. But juries in the federal court for the western district of Washington found Olmstead and seventeen of his partners and managers guilty, and the Court of Appeals for the Ninth Circuit affirmed the convictions and jail sentences.

The Meaning of the Fourth Amendment

From the beginning, Olmstead’s lawyers had argued that the use of wiretap evidence obtained without a search warrant violated the Fourth Amendment to the Constitution, and they now brought that argument to the U.S. Supreme Court. His lead attorney, John F. Dore, claimed that the rights guaranteed under the Constitution are “indispensable to the full enjoyment of personal security, personal liberty, and private property,” and therefore may not be trampled upon by the government. If the government used fraud or subterfuge to secure evidence, then it could not be admitted as evidence in a case. Dore also tried to convince the Court that even if there had not been an actual invasion of the physical premises, if the results were to force a person to furnish evidence against himself, then it violated the Fifth Amendment’s prohibition against self-incrimination.

American Telephone & Telegraph, the nation’s largest provider of phone service, as well as a number of smaller telephone firms, filed briefs as amici curiae, or friends of the court, protesting against the use of private conversations, secured through wiretaps, as violations of the Fourth and Fifth Amendments.

Olmstead had some good arguments on his side, but no case up to that time had actually dealt with the use of wiretap evidence. The Fourth Amendment, adopted as part of the Bill of Rights in 1791, held that “The right of the people to be secure in their persons, houses, papers, and effects, against unreasonable searches and seizures, shall not be violated, and no Warrants shall issue, but upon probable cause, supported by Oath or affirmation, and particularly describing the place to be searched and the persons or things to be seized.” If nothing else, the amendment prohibited the general warrants common in the last years of colonial America, where the British Crown’s agents could search anyone’s home without showing cause or even telling a magistrate what they were seeking. Under the Fourth Amendment there could be no “fishing expeditions” of this type.

The Fifth Amendment included a number of safeguards for persons accused of crimes, including indictment by a grand jury and a ban on double jeopardy, but a key part read that no person “shall be compelled in any criminal case to be a witness against himself.” When Olmstead’s case reached the Supreme Court in February 1928, the jurisprudence of these protections could best be described as slim. The Court had heard a few cases, but not very many, and since lawyers both for the government as well as for Olmstead cited all of them, they clearly did not create a clear line of precedents. The Fourth Amendment thus became central to the arguments for both sides, and both relied on three earlier cases.

The Court first heard a Fourth Amendment challenge in 1886, and even then the argument was made that papers secured without a warrant not only violated the search and seizure clause of the Fourth Amendment, but also the self-incrimination clause of the Fifth Amendment. E. A. Boyd & Sons allegedly entered into an arrangement with Union Plate Glass Company to import plate glass with the intention of avoiding the tariffs imposed by the 1874 Customs Act. The U.S. attorney directed the Boyds to produce their invoices for the glass, and they challenged the validity of the order under the Fourth and Fifth Amendments. Eventually the Boyds handed over the documents, which the government used to secure a conviction for evasion of tariffs, and they appealed.

A unanimous Court reversed that conviction in Boyd v. United States (1886). Justice Joseph P. Bradley stated that the Fourth and Fifth Amendments protected the privacy of individuals from government intrusion, and applied not only in criminal cases but—and this was the most important part in regard to Olmstead—even where there had been no physical invasion of property. The Court struck down the provision of the Customs Act authorizing compulsory production of evidence as unconstitutional, and therefore the invoices could not be used against the Boyds.

Boyd led directly to the next major Fourth Amendment case, Weeks v. United States (1914), in which the Court expanded the protections of the Fourth Amendment. Federal marshals, aided by state officers, searched and arrested Freemont Weeks at the Union Station in Kansas City, Missouri. They had no warrant, but the papers they seized led to Weeks’s conviction of using the mails to transport lottery tickets. Prior to his trial he demanded the return of his effects and objected to their use at the trial, thus laying a basis for appeal to the high court.

Speaking for a unanimous court, Justice William R. Day took a major step in providing for an enforcement mechanism against Fourth Amendment violations—the exclusionary rule. The warrantless search as well as the trial court’s refusal to return Weeks’s property had been a violation of his constitutional rights of personal security, personal liberty, and private property. Day relied exclusively on Fourth Amendment grounds to order the judgment reversed, and completely ignored the Fifth Amendment claims Weeks had raised.

A few years later the Court, disgusted by the methods of the government in the postwar Red Scare, signaled its displeasure at federal abuse of constitutionally protected rights in another Fourth Amendment case, Silverthorne Lumber Company v. United States (1920).

In Silverthorne two men had been arrested after indictment by a grand jury. Agents of the Justice Department, without a warrant, then ransacked their office, removing books, papers, and other documents. Justice Oliver Wendell Holmes Jr., writing for the Court, branded the government’s action an “outrage” and blocked any use of the illegally seized material by the government in legal proceedings. Holmes’s insistence that the documents “shall not be used at all” helped expand the exclusionary rule hinted at in Boyd and more fully enunciated in Weeks. The decision stressed two themes: the exclusionary rule provided the only effective means of protecting Fourth Amendment rights, and judicial integrity required that the courts not sanction illegal searches by admitting the fruits of this illegality into evidence.

Given this clear line of precedents, one would have thought that the Court in Olmstead’s case would have precluded use of the warrantless wiretap evidence. A bare majority of the Court, however, refused to accept the Fourth Amendment argument, and instead agreed with the government’s lawyer, Michael J. Doherty, that wiretapping did not constitute an unreasonable search and seizure within the meaning of the Fourth Amendment, and that evidence secured through a wiretap could be used at a trial.

Chief Justice Taft’s Opinion

Chief Justice William Howard Taft wrote the majority opinion, joined by Justices Willis Van Devanter, James C. McReynolds, George Sutherland, and Edward T. Sanford. Taft tried to limit the decision to what he termed was the sole question that the Court had agreed to hear in accepting the case for review—whether “the use of evidence of private telephone conversations between the defendants and conversations between the defendants and others, intercepted by means of wire tapping, amounted to a violation of the 4th and 5th Amendments.”

In what can only be described as a wooden opinion, Taft went over all of the Supreme Court’s prior Fourth Amendment opinions and found them irrelevant to the Olmstead case. The precedents had all involved physical intrusion into the defendants’ homes or offices, and in this instance the federal agents had done no more than listen in on conversations from positions outside the premises. “There was no evidence of compulsion to induce the defendants to talk over their many telephones,” he said. “They were continually and voluntarily transacting business without knowledge of the interception.” As for the alleged violations of the Fourth Amendment, Taft declared, “The Amendment does not forbid what was done here. There was no searching. There was no seizure. 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.”

Taft could find no means by which this activity violated the Fourth Amendment. “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,” he said. “The intervening wires are not part of his house or office, any more than are the highways along which they are stretched.” Then Taft, who in other cases had no problem in reaching out to make new law, adopted the posture of strict judicial restraint. Congress could, he noted, make evidence secured by wiretap inadmissible in federal trials, but “courts may not adopt such a policy by attributing an enlarged and unusual meaning to the Fourth Amendment.”

Why did Taft, who certainly knew that the prior cases from Boyd to Weeks to Silverthorne Lumber had all strengthened the protections of the Fourth Amendment, write an opinion in Olmstead that weakened them? One answer is that a majority of the justices supported the Noble Experiment. Three members of the Court—Pierce Butler, George Sutherland, and James McReynolds—detested Prohibition because they opposed the expansion of the national administrative state; they also believed that positive law, i.e., statutory enactments, should not be used to overthrow established social values. Taft wrote to his brother that “Holmes, Van Devanter, Brandeis, Sanford and I are steady in the boat.” Taft was not sure about the newest member of the Court, Harlan Fiske Stone: he “wobbles a good deal on the subject, and I don’t quite see where he stands, and I am not quite sure that he does.”

Holmes and Brandeis had bowed to the will of the people in accepting Prohibition, although in practice Holmes continued to enjoy his drink and to receive bottles from his friends. Brandeis had liked his beer and an occasional whiskey, and for many years at dinner he had served guests the good Kentucky bourbon that his brother Alfred regularly sent from Louisville. His views on democratic governance led him to support Prohibition after ratification, and in time he even came to be a fervent supporter of the ban on alcohol, believing it could improve the lives of working people. On the most extreme end, Taft and Van Devanter saw opposition to dryness as resistance to the legal order itself.

During the 1920s a majority of the Court consistently found in favor of the government in cases involving Prohibition. The Court had upheld the War-Time Prohibition Act, and then approved the Volstead Act that implemented the Eighteenth Amendment. Even the Tenth Amendment, which reserved powers to the states and which was a darling of conservative federalists, fell before the needs to banish Demon Rum. As Justice Sanford wrote in a 1924 case, Everard’s Breweries v. Day, since Prohibition “is within the authority delegated to Congress by the Eighteenth Amendment, its validity is not impaired by reason of any power reserved to the States.” Fear of overweening national authority, a bedrock of conservative as well as federalist thought since the founding of the Republic, vanished in the Taft Court’s enthusiasm for the Noble Experiment.

In a variety of cases the Court majority allowed the government to close distilleries without compensation to the owners, ruled that the ban on double jeopardy did not apply when a person had been convicted of one crime for possessing alcohol and then convicted in another trial for selling the same liquor, permitted the government to confiscate an automobile that carried illegal alcohol, upheld a congressional ban on the common prescription of wine and liquor for medicinal purposes, and allowed searches of cars for contraband without a warrant.

Justices Butler and Holmes Dissent

The Taft opinion elicited dissents from Butler, Holmes, and Brandeis. In a well-reasoned historical analysis, the generally conservative Butler repudiated Taft’s sterile interpretation of what the Fourth Amendment meant, although he agreed with Taft that the only question properly before the Court was whether the evidence itself could be used. Stone, who concurred in all of the dissents, did not agree with this part of Butler’s writing. Although the grant of certiorari accepting the appeal identified a single issue, he believed that the Court was always free to consider any matter part of the record, and in this regard found himself in agreement with Holmes and Brandeis.

Holmes took a different tack from Butler and, in a comment that soon caught the liberal imagination, condemned wiretapping as a “dirty business.” He identified two “objects of desire,” noting that one could not have both. “It is desirable that criminals should be detected, and to that end all available evidence should be used. It also is desirable that the government should not itself foster and pay for other crimes, when they are the means by which the evidence is to be obtained.” We have to choose, he declared, “and for my part I think it a less evil that some criminals should escape than that the government should play an ignoble part.” Holmes had originally not intended to write an opinion at all, since “My brother Brandeis has given this case so exhaustive an examination,” but he did so for two reasons. First, Brandeis had privately asked him to do so, and second, he did not completely agree with all that Brandeis said, especially that the Fourth and Fifth Amendments created rights of privacy that covered the defendant.

The Brandeis Dissent and the Right of Privacy

It was Justice Brandeis, however, whose dissenting opinion had the most profound and lasting impact on Fourth Amendment jurisprudence. Brandeis used his dissent to drive home several points. He clearly abhorred the methods used by the Prohibition agents, and the reason for his antipathy is one that should be read every day by government officials up to and including presidents:

Decency, security and liberty alike demand that government officials shall be subjected to the same rules of conduct that are commands to the citizen. In a government of laws, existence of the government will be imperilled if it fails to observe the law scrupulously. Our Government is the potent, the omnipresent teacher. For good or for ill, it teaches the whole people by its example. Crime is contagious. If the Government becomes a lawbreaker, it breeds contempt for law; it invites every man to become a law unto himself; it invites anarchy. To declare that in the administration of the criminal law the end justifies the means—to declare that the Government may commit crimes in order to secure the conviction of a private criminal—would bring terrible retribution. Against that pernicious doctrine this Court should resolutely set its face.

But Brandeis had another argument to make, one that he had been advocating for nearly four decades—the right to privacy. In an 1890 article he had written with his law partner, Sam Warren, Brandeis had relied on common law private action and tort law, since the alleged violators of privacy had been the press and commercial actors. Now, because the government had been involved, he identified personal privacy as a matter of constitutional law, and married his earlier notion of the right to be let alone with the Fourth Amendment’s ban on unreasonable search and seizure and the Fifth Amendment’s protection against self-incrimination. To justify reading privacy into these amendments, he assigned his law clerk that term, Henry J. Friendly, to researching the circumstances surrounding the drafting of the Fourth Amendment. Brandeis expected his clerks to argue with him, and when they did make a convincing argument, he would listen. At first the justice wanted to base his dissent on the violation of the Washington State statute against wiretapping, but Friendly convinced him that it must rest on a constitutional basis. The result is one of the landmark dissents in constitutional history.

Taft had emphasized that the Framers had nothing more in mind than the general warrants used by the British in the 1760s and 1770s, and the Fourth Amendment applied to little else. Brandeis cited Chief Justice Marshall’s reminder that “We must never forget that it is a constitution we are expounding.” Times had changed since 1791, and Brandeis cited case after case as well as historical treatises to show that the Court had constantly read constitutional provisions to take into account conditions never envisioned by the Framers. The technical nature of the federal agents’ entry onto the defendant’s property did not matter as much as the intent of the amendment to protect people in their homes and businesses. “Time works changes, brings into existence new conditions and purposes. Subtle and more far-reaching means of invading privacy have become available to the Government. 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.” (At this point Brandeis wanted to refer to a new device recently developed by the General Electric Company called “television,” but removed the note in deference to Friendly’s skepticism.)

He then went on to write one of the most eloquent—and most quoted—passages in American law:

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 protect 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 dismissed Taft’s mechanistic view that no intrusion had occurred, since it did not matter where the actual physical connection with the telephone wires took place:

And it is also immaterial that the intrusion was in aid of law enforcement. Experience should teach us to be most on our guard to protect liberty when the Government’s purposes are beneficent. Men born to freedom are naturally alert to repel invasion of their liberty by evil-minded rulers. The greatest dangers to liberty lurk in insidious encroachment by men of zeal, well-meaning but without understanding.

In the Olmstead dissent Brandeis reinvented Fourth Amendment jurisprudence. Taft’s majority opinion, as well as prior search and seizure cases, had been grounded in conceptions of property, whether or not police had actually entered the home or business. Brandeis shifted the emphasis from where the alleged wrong took place to how it affected the individual’s rights. While Brandeis disliked the “dirty business” of wiretapping as much as Holmes, for him the more important issues were the conduct of the police and the individual’s right to be let alone. If the police had probable cause to suspect a person of wrongdoing, the Constitution required that a warrant be secured. Warrantless searches, except in very special circumstances, could not be allowed.

Chief Justice Taft reacted furiously to the dissents. “If they think we are going to be frightened in our effort to stand by the law and give the public a chance to punish criminals,” he told his brother, “they are mistaken, even though we are condemned for lack of high ideals.” He believed that Brandeis had gone off on what he considered irrelevant ethical issues, and termed Brandeis “the lawless member of the Court” for having done so. Holmes had written “the nastiest opinion,” and Taft claimed that Holmes had voted the other way “till Brandeis got after him and induced him to change.” But, he told Justice Sutherland, “I hope that ultimately it will be seen that we in the majority were right.”

Taft also was incensed that the dissents went beyond what he termed the only question that the Court had agreed to review. “Some of our number, departing from that order, have concluded that there is merit in the twofold objection overruled in both courts below that evidence obtained through intercepting of telephone messages by government agents was inadmissible because the mode of obtaining it was unethical and a misdemeanor under the law of Washington.” Taft then went into a lengthy exposition of the law of evidence, citing various legal treatises all purporting that even evidence illegally obtained may be submitted without triggering any sort of constitutional violation. The fact that Washington State law prohibited wiretapping did not control the behavior of federal agents, nor the validity of the evidence they gathered while listening in on conversations.

Taft’s prediction proved wrong, although it took many years before Brandeis’s dissent became established as a constitutional right in Griswold v. Connecticut (1965). Brandeis did, however, live to see Congress prohibit wiretapping evidence in federal courts in the Federal Communications Act of 1934, and the Court to partially reverse Olmstead in 1937. In 1967 the Supreme Court fully adopted Brandeis’s position and overturned Olmstead completely, bringing wiretapping within the ambit of Fourth Amendment protection. That same year, Justice Potter Stewart explained the Court’s new philosophy in words that grew directly out of Brandeis’s dissent—“The Fourth Amendment protects people, not places.” In a more recent case, Kyllo v. United States (2001), Justice Antonin Scalia used the logic of Brandeis’s dissent to hold that federal agents could not use a new technology, thermal imaging, to look through the walls of Danny Lee Kyllo’s house to determine if the occupant was growing marijuana. Even though the agents used the machine outside the premises, they had secured information about the inside, and could not use that evidence without a warrant.

Roy Olmstead Reforms

Following the Supreme Court’s affirmation of the conviction, federal agents brought Roy Olmstead to the prison on McNeil Island to serve out his four-year term. On May 12, 1931, he was released with time off for good behavior. The Seattle he returned to was, of course, suffering from the Great Depression, but little had changed in the bootlegging business other than that a new group of rumrunners supplied liquor to the citizenry. Then in November 1932 Washington repealed all of its Prohibition enforcement laws, and a year later Franklin Roosevelt announced the ratification of the Twenty-first Amendment, repealing Prohibition altogether. On Christmas Day, 1935, President Roosevelt granted Olmstead a full presidential pardon, restoring his constitutional rights, and also remitted him $10,300 in costs.

During his time on McNeil Island Olmstead studied carpentry, and he also became a Christian Scientist. After his release he made his living for a while selling furniture, but he began devoting more and more time to his vocation as a Christian Science minister, visiting Seattle jails to talk and give solace to the inmates, and helping to rehabilitate some of them. He ran his ministry out of a small, unobtrusive office, but he remained a newsworthy personality throughout his life. He gave an interview to the Seattle Post-Intelligencer just a year before his death in 1966, at age eighty.

Cases Cited

Boyd v. United States, 116 U.S. 616 (1886)

Griswold v. Connecticut, 381 U.S. 419 (1965)

James Everard’s Breweries v. Day, 265 U.S. 545 (1924)

Kyllo v. United States, 533 U.S. 27 (2001)

Olmstead v. United States, 277 U.S. 438 (1928)

Silverthorne Lumber Company v. United States, 251 U.S. 385 (1920)

Weeks v. United States, 232 U.S. 383 (1914)

For Further Reading

For Prohibition see Thomas R. Pegram, Battling Demon Rum: The Struggle for a Dry America, 1800–1933 (1988), and Richard F. Hamm, Shaping the Eighteenth Amendment: Temperance Reform, Legal Culture, and the Polity, 1880–1920 (1995). The history of the Fourth Amendment is explored in Thomas N. McInnis, The Evolution of the Fourth Amendment (2009), and its relation to privacy is developed in David L. Hudson, The Right to Privacy (2009), and Frederick S. Lane, American Privacy (2009). The effect of Prohibition on the Taft Court is examined in Robert Post, “Federalism, Positive Law, and the Emergence of the American Administrative State: Prohibition in the Taft Court Era,” 48 William and Mary Law Review 1 (2006). For Brandeis and his concern about privacy, see Melvin I. Urofsky, Louis D. Brandeis: A Life (2009); the writing of the opinion is examined in Paul A. Freund, “The Evolution of a Brandeis Dissent,” Manuscripts 10 (Spring 1958): 18–25, 34.