How the Drug War Convinced America to Wiretap the Digital Revolution

Operation Root Canal

HUMANITIES, Winter 2023, Volume 44, Number 1

On May 6, 1990, the Baltimore Sun published a front-page article on an embattled Baltimore Police Department investigation. The target was Linwood “Rudy” Williams, the leader of a violent drug organization that had for years controlled the streets of Charm City. Federal agents had arrested Williams and 29 other suspects two weeks earlier, but only after an unexpected logistical problem almost forced them to abandon the case. Williams, it turned out, owned a mobile phone. He had exploited its features to keep the police from capturing his voice on a wiretap recording.

mug shot of Rudy Williams
Photo caption

During the 1980s and 1990s concern about drug-related crimes, like those committed by Baltimore’s Linwood “Rudy” Williams, led to the implementation of the FBI’s Operation Root Canal and the passage of the Communications Assistance for Law Enforcement Act.

—Baltimore Police Department

film still from The WIre
Photo caption

Actors Jamie Hector and Felicia Pearson in the popular HBO series The Wire, which portrayed the efforts of Baltimore drug dealers to evade police wiretaps in a new era of ubiquitous cell phones. 

—RGR Collection / Alamy Stock Photo

The Sun presented the Williams investigation as emblematic of the challenges that American law enforcement agencies were starting to encounter in a changing technological environment. For the average American consumer, new innovations were making electronic communications more reliable and more convenient. But for agents of the law—especially those charged with waging the War on Drugs—those same innovations were causing headaches. From fiber optic cables to two-way pagers, and from fax machines to cell phones, the era’s latest communications advancements were thwarting the surveillance techniques that police routinely employed in narcotics investigations. Faced with the threat of “going dark,” U.S. law enforcement agencies were looking to the telecommunications industry for wiretap assistance.

“Dialogue is likely to prove essential if law enforcement officials are going to keep pace with technology,” the Sun report concluded, hinting at an impending crisis for the nation’s drug warriors. “Technical refinements will help, but nothing can change the fact that telephone communications have permanently transformed the drug trade.

The author of the Sun article was David Simon, an enterprising police reporter who has become a major name in the television industry. More than a decade later, Simon used his experience on the Baltimore law enforcement beat as the basis for his celebrated HBO series The Wire (2002–2008). Fans of The Wire will doubtless recognize similarities between the Linwood Williams investigation and the show’s principal narrative arc, which follows a fictional unit of Baltimore detectives who attempt to fight the drug war in an age of pagers, cell phones, and computer messages. Williams himself provided inspiration for the character of Marlo Stanfield (played by Jamie Hector), the ruthless kingpin who wrests control of the city’s heroin trade in the show’s third season.

But before it became fodder for cable TV drama, Simon’s reporting was the product of a simmering debate over the relationship between technology and crime control in the United States. Should communications firms cooperate with law enforcement in the name of national security and crime control, or should they work to protect the privacy of consumers and citizens? Should the police have easy access to our conversations, our messages, and our data, or should new devices and systems be hardwired to foil snoopers and spies?

Such questions remain urgent today. But they have a long and sinuous history. In the case of Linwood Williams—on the streets of Baltimore, a world away from the boardrooms of Silicon Valley and the halls of Congress—the imperatives of the drug war were forcing the nation to confront a story about wiretapping as old as the wires themselves.

The practice of wiretapping dates to the American Civil War, the world’s first military conflict in which the use of electronic communications played a significant role. Signal operators working for both the Union and the Confederacy tapped telegraph lines to intercept enemy dispatches and transmit disinformation. Yet official agents of the state seldom followed their lead in the postbellum years. It was much easier to subpoena the duplicate messages stored in the files of every telegraph office than to sit idly on the line, waiting to intercept electronic signals in real time.

The workings of the telephone system proved more enticing to law enforcement. Almost as soon as common carriers began establishing centralized telephone exchanges at the end of the nineteenth century, local police began monitoring their lines. But more often than not, the earliest police wiretappers depended on the willing assistance of telephone service providers to do their work. In the early decades of the twentieth century, for example, the New York Police Department (NYPD) housed its wiretap squad on the third floor of an office building located at 50 Church Street, in the heart of lower Manhattan. Every one of their phone taps—as many as 350 per year by the mid 1910s—went up with the New York Telephone Company’s help. To initiate the operation, the NYPD commissioner typically sent a boilerplate notice to the head of the firm’s technical services division: “I have reason to believe that the following telephone is being used for criminal purposes, and respectfully request the co-operation of your company in detecting this matter.”

black and white photograph of FBI circa 1930 listening to a phone line
Photo caption

An FBI agent uses a portable phone during an operation, circa 1930. During the twentieth century, rapid innovations in communications technology have enabled—and at times stymied—the efforts of police to collect evidence against criminal suspects.

 —Universal History Archive / UIG / Bridgeman Images

Surveillance cooperation between law enforcement and the telecom industry only intensified in the coming decades—almost always off the record, and in the gray areas of the law. AT&T’s operating companies frequently leased private wiretap lines to local and state police departments, an arrangement that telecommunications officials euphemistically termed “bridging” or “censoring.” Leased-line wiretaps enabled detectives to conduct round-the-clock telephone surveillance from the security of a remote location, and even listen to multiple calls at once. Telephone carriers also readily coughed up other forms of customer data—dialed number registries, cable and appearance locations, even billing records—in order to assist with ongoing criminal investigations. By the middle of the twentieth century, law enforcement training manuals encouraged detectives to develop friendly contacts at the local phone company. Easy access to the telephone network was regarded as essential to modern police work.

In 1968, Title III of the Omnibus Crime Control and Safe Streets Act legalized police wiretapping under judicial oversight. But the law remained silent on the issue of telecom industry cooperation. Two years later, a bipartisan vote in Congress quietly ratified an amendment to the Title III wiretap provisions, requiring phone companies to provide the “information, facilities, and technical assistance necessary to accomplish . . . [a wiretap] interception unobtrusively and with minimum disruption of service.” In 1977, the U.S. Supreme Court rebuffed a legal challenge to the technical assistance amendment in United States v. New York Telephone Company. A 5-4 majority ruled that the government had the authority to compel providers to furnish “any assistance necessary” to install a warranted wiretap. By the late 1970s, cooperation between the police and the telecommunications industry—one of the electronic age’s dirtiest secrets—was out in the open, a matter of settled law.  

All of this provided the backdrop to the Baltimore Police Department’s arrest of Linwood Williams in May 1990. The problem was that two major developments had upset the collaborative arrangement between law enforcement and the telecommunications industry in the intervening years. The first development was technological. The fall of the Bell System monopoly in the early 1980s had ushered in an era of unprecedented innovation in the field of telecommunications. A newly competitive marketplace had yielded a host of new devices, features, and systems—the earliest glimmerings of the digital revolution. Many of them were designed with privacy and security in mind.

The second development was political. A new generation of tough-on-crime lawmakers, President Ronald Reagan chief among them, had redoubled America’s efforts in the War on Drugs. Flush with an infusion of cash and manpower, police agencies on the drug war’s front lines suddenly had the resources to mount extensive narcotics investigations. They soon came to rely on the Title III wiretap as their most trusted weapon against sophisticated trafficking networks. Between 1980 and 1984 alone, the annual number of police wiretaps installed across the United States ballooned by more than 40 percent. The average length of a telephone intercept extended from 24 hours to 26 days.

The combination of accelerated technological change and skyrocketing surveillance demand set law enforcement on a collision course with the telecommunications industry. Soon the issue of “wiretap interference” came to preoccupy police officials who were under pressure to clean up the nation’s streets. In New York, members of the Colombian Cali drug cartel outwitted a federal investigation by purchasing dozens of cheap mobile phones and discarding them after only a few uses. In New Jersey, another hotbed of drug war wiretapping, new landline features such as call waiting and call forwarding stymied even the most competent surveillance technicians. A Title III order might have enabled the police to monitor a single caller using a standard telephone handset. But if the same caller clicked over to a second conversation, or routed an incoming signal to an answering machine or voicemail service, the wiretap ceased to function. 

It was the FBI, working concurrently with the Drug Enforcement Administration, that was running the majority of the government’s drug war wiretaps. So it was the FBI that first sounded the alarm about the threat of wiretap interference in the digital age. Bureau representatives began petitioning telephone industry executives in the fall of 1990, a few months after the Baltimore Sun ran David Simon’s front-page report on Linwood Williams. In a series of confidential memoranda, the FBI enumerated its surveillance difficulties in tedious technical detail, hoping to illustrate that telecom industry assistance “must logically increase as the complexity of the technology increase[s].” The argument was simple: Without a coordinated overhaul of phone company systems, the Bureau would be out of the wiretapping business altogether. 

Yet the initial solutions the FBI posed to the wiretap interference problem were prohibitively expensive. What’s more, the reports of technical difficulties from the Bureau’s field officers were anecdotal. Investigators later discovered that the FBI’s projections about the threat to law enforcement surveillance power were based on faulty statistics. When the phone companies refused to budge, the Bureau began exploring more drastic options.

Enter Operation Root Canal: a top-secret FBI effort to create a backdoor to the digital communications revolution. The plan, first formulated in January 1992, essentially amounted to a political pressure campaign, designed to force telecommunications firms to build surveillance capacities into the infrastructure of the telephone network. Proclaiming the imminent collapse of U.S. law enforcement’s wiretapping powers, the FBI began lobbying Congress to make electronic surveillance a permanent feature of communications hardware.

It was a bold proposition. One civil liberties activist later described the idea as tantamount to “requiring the telephone network to have vulnerabilities intentionally built into it.” But the tough-on-crime imperatives of the early 1990s, fueled by the drug war, outweighed more abstract considerations of privacy and security. By 1993, the FBI’s newly appointed director, Louis Freeh, had all but assured Operation Root Canal’s victory in Congress. Freeh made the prioritization of the wiretap interference issue a precondition for his nomination as Bureau chief. With the blessing of President Bill Clinton, another tough-on-crime drug warrior, Freeh canvassed Capitol Hill to promote the issue of incorporated surveillance assistance. At times, he resorted to brazen scare tactics to make his case.

“If you think crime is bad now, just wait and see what happens if the FBI one day soon is no longer able to conduct court-approved electronic surveillance,” Freeh remarked in a closed-door speech to lobbyists and judges at the American Law Institute in 1994. In a characteristically inflammatory flourish, he warned that the Bureau’s loss of wiretap capacity would lead to “increased loss of life” and the “increased availability of much cheaper illegal drugs.” He cited inflated statistics about “hundreds” of thwarted Title III wiretaps to give weight to his account.

Louis Freeh and Bill Clinton at a podium
Photo caption

With the support of President Bill Clinton, FBI Director Louis Freeh, left, successfully lobbied Congress to require that telephone companies assist the government with the interception of wire and electronic communications. 

—Mark Reinstein / Alamy Stock Photo

After a year of negotiations among lawmakers and telecommunications officials, Operation Root Canal won out. The bipartisan bill that emerged from the campaign was dubbed the Communications Assistance for Law Enforcement Act (CALEA). CALEA charged American phone companies with helping the government intercept “all wire and electronic communications carried by the carrier within a service area,” and provide “features or modifications as are necessary to permit such carriers to comply with [wiretap] capability requirements.” In return, Congress offered the phone companies $500 million to help defray the cost of updating existing systems and manufacturing new equipment. President Clinton signed CALEA into law on October 25, 1994, a little more than a month after enacting the punitive crime bill—which included the “three strikes” provision—for which he has since become synonymous.

The Communications Assistance for Law Enforcement Act was an extraordinary piece of federal legislation. Before CALEA, the needs of policing and crime control were incidental to the regular workings of the telephone system. After CALEA, telephone networks were designed to facilitate court-ordered surveillance from start to finish. Capitalizing on the politics of the drug war, Operation Root Canal had reoriented the relationship between technology and policing in America. For the first time in the nation’s history, the need to conduct routine electronic surveillance was incorporated into the circuitry of new devices and systems themselves. 

CALEA is still good law, and its provisions now cover many of the digital age’s most important communications platforms. When we consider the origins of the regime of ubiquitous backdoor surveillance under which we live today, we should think neither of the national security priorities of the War on Terror nor even of the campaigns against Communist subversion and antiwar activism that motivated many of the U.S. government’s most notorious abuses of electronic surveillance power long beforehand. We should think, instead, of the War on Drugs. We should think of Linwood Williams using a mobile phone—and of the politics behind a nation’s doomed attempt to stop him.