Illustration: Joan Wong; Associated Press; Bettmann / Getty

My Family Story of Love, the Mob, and Government Surveillance

The whole truth took me decades to learn.

On June 16, 1975, when I was 12 years old, my mother, Brenda, married Charles “Chuckie” O’Brien, who a few weeks later would become a leading suspect in the notorious disappearance of Jimmy Hoffa, the former president of the Teamsters union.

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Chuckie had known Hoffa since he was a boy, loved him like a father, and was his closest aide in the 1950s and ’60s, when Hoffa was the nation’s best-known and most feared labor leader. Soon after Hoffa went missing, on July 30, 1975, the FBI zeroed in on Chuckie. Chuckie had been by Hoffa’s side during Attorney General Robert F. Kennedy’s long pursuit of Hoffa for Mob ties and union corruption, and in 1967 it was Chuckie who had accompanied Hoffa when his boss reported to federal marshals and began a nearly five-year prison term. But in late 1974, Chuckie and Hoffa had had a falling out, and a slew of circumstantial evidence connected Chuckie to the disappearance. The FBI quickly concluded that Chuckie had picked up Hoffa and driven him to his death—a theory that has currency to this day, at least in the public mind.

The government never proved Chuckie’s involvement, and Hoffa’s remains have never been found. But the Hoffa investigation enveloped Chuckie and eventually ruined his life. In the midst of this maelstrom, Chuckie and I grew close. He formally adopted me when I was 13, and found time despite his legal troubles to give me the love and attention I had never received from my biological father. I revered Chuckie in my teens. The wise guys I met through him were kind and, to my young eyes, upright gentlemen. And it was thrilling to be associated with the Teamsters union in an era—typified by C. W. McCall’s hit song “Convoy” and the adventures of Burt Reynolds in Smokey and the Bandit—that glorified trucker defiance of authority.

When I left home for college, I read for the first time books that confidently pinned Hoffa’s disappearance on Chuckie. I also came to understand that the Mafia was real and dangerous, and that Chuckie had a history of criminal acts ranging from theft to assault. By the time I went to law school, I had grown apprehensive about Chuckie’s potential impact on my life. In my mid-20s I broke with him, brutally and completely. This proved to be a good career move; otherwise, I never would have obtained the security clearances I later needed for several government jobs, which culminated in a 2003 appointment by George W. Bush to be the assistant attorney general in charge of the Justice Department’s Office of Legal Counsel.

It was during that Justice Department stint, more than 15 years after I renounced Chuckie, that I reconsidered some of the things he had told me in my teens about executive-branch abuses and concealments. That reconsideration would eventually lead me to seek his forgiveness and then, after years of conversations and research, to conclude that he was innocent in Hoffa’s disappearance. What led me down this improbable path was my work on Stellarwind, President Bush’s post-9/11 anti-terrorist program of warrantless surveillance activities inside the United States, conducted by the National Security Agency, which swept up vast amounts of information about innocent Americans.

In my youth, Chuckie had spewed bile about Bobby Kennedy’s surveillance abuses against him, Hoffa, and their friends in organized crime. “They can break every law there is, but they got ‘backup,’ ” Chuckie would say, referring to the government’s tendency to skirt the law in secret even as it enforced the law against others, and to justify its actions by claiming executive authority.

For decades, I had dismissed Chuckie’s assessment as uninformed and self-serving. But while working on Stellarwind, I discovered that he had been right. Executive-branch lawyers had approved the program in secret even though it was difficult to square with congressional restrictions on government surveillance. Such “backup,” I came to realize, was a crucial element in a recurrent pattern in the history of government surveillance: The executive branch, responsible for security, employs the latest technology against an enemy within, and in the process, it often quietly bends or breaks the law; after scandalous revelations, it secures new legislation to put the surveillance practices on a sounder legal footing; finally, a “new normal” is established before the cycle begins anew.

I did not know much about the history of government surveillance, or the government’s accompanying abuse of the law, when I began work on Stellarwind. Much of that history, especially about the Justice Department’s accommodating role, is still not widely understood.

Since the invention of the telephone and the miniature microphone, the government has used these technologies in criminal and national-security investigations to listen in on private communications without the targets’ knowledge. The government’s appetite for the valuable information it gathers from wires, bugs, and other forms of electronic surveillance has always been insatiable. Congress and the courts have intermittently imposed legal restrictions to check the obvious threat to privacy this appetite poses. But under pressure to find and defeat various subversive forces in American society, real or imagined, the executive branch has always found secret work-arounds.

Among the early targets, I came to learn, were Nazi spies inside the United States. On December 11, 1939, three months after Hitler invaded Poland, the Supreme Court ruled that a federal statute barred the government from using evidence gleaned from wiretaps in court. Attorney General Robert Jackson quickly announced a ban on wiretapping. But President Franklin D. Roosevelt overruled Jackson after FBI Director J. Edgar Hoover complained that the ban made it too hard to meet the growing menace of spies and saboteurs on American soil. FDR acknowledged in a secret memorandum that government wiretapping “is almost bound to lead to abuse of civil rights.” But he concluded, unconvincingly, that “the Supreme Court never intended any dictum … to apply to grave matters involving the defense of the nation.” Jackson acquiesced, and government wiretapping continued.

Henceforward, whenever a legal obstacle to electronic surveillance arose, Hoover would complain to his Justice Department or White House superiors about the dangers of going dark. Given the urgency of finding and defeating the enemy, these officials tended to interpret away the limits on lawful executive action—a task made easier by the fact that decisions usually were arrived at in secret, beyond judicial scrutiny.

Hoover’s next need for backup concerned a different threat to national security (communism) and a different technology (microphone bugs). In the course of its investigations, the FBI often broke into homes or offices to plant bugs. In a 1954 opinion, Robert Jackson, by then a Supreme Court justice, made clear that this practice “flagrantly” violated the Fourth Amendment’s prohibition of unreasonable searches and seizures. But Hoover wrote to the attorney general at the time, Herbert Brownell Jr., to emphasize the stakes for national security should bugs be barred. Brownell then secretly authorized the FBI to resume bugging spies, saboteurs, and other “subversive persons,” even if that meant physical invasion of homes and offices, because “considerations of internal security and the national safety are paramount.”

Hoover wasn’t done. In the late ’50s, he wanted to extend microphone surveillance to meet a different threat from a different kind of enemy within: not foreign subversion but the domestic criminal activities of gangsters. Bugging possible foreign agents was already a legal stretch. Bugging the Mob was an even bigger stretch, because breaking in to plant bugs on suspected domestic criminals goes to the core of what the Fourth Amendment prohibits. Hoover’s FBI went there anyway, based on a preposterous interpretation of Brownell’s questionable secret ruling. The next attorney general, William Rogers, knew what the FBI was doing and went along with it. The bugging remained hidden from the public.

Rogers’s successor, Robert F. Kennedy, continued this “don’t ask, don’t tell” approach to the use of bugs as part of the campaign against organized crime. He pushed the FBI to confront the Mob more aggressively, and he eagerly consumed the fruits of Hoover’s surveillance. When the bugging was finally revealed, in the mid-’60s, Kennedy denied knowledge of any illegality. A great deal of evidence suggests that he was not being candid. And as the journalist Victor Navasky has noted, “To the extent that Kennedy was ignorant of the FBI’s bugging practices, it was an administrative failure so flagrant that Kennedy is morally chargeable with the consequences of his ignorance.”

Teamsters President Jimmy Hoffa and his aide Chuckie O'Brien leave the federal courthouse in Chattanooga, Tennessee
Teamsters President Jimmy Hoffa (left) and his aide Chuckie O'Brien leave the federal courthouse in Chattanooga, Tennessee, during Hoffa’s trial for jury tampering. (Robert W. Kelley / Life Picture Collection / Getty)

The FBI made secret recordings from the hundreds of microphones it installed during the Kennedy years. Unbeknownst to Chuckie, the FBI frequently picked him up on two of them. In early 1961, the bureau placed one of the bugs in the office of the Detroit Mafia capo Anthony Giacalone, with whom Chuckie had been close since he was a boy. It later placed a bug in the apartment of Sylvia Pagano, Chuckie’s mother, in Detroit’s riverfront Gold Coast neighborhood.

The FBI was interested in Giacalone because of his criminal activities and because he had done business with Hoffa for decades. It was interested in Pagano because she worked with Giacalone and was close to Hoffa. Pagano had introduced Hoffa to the Detroit crime family, and to Chuckie, in the early ’40s. She had enormous influence with Hoffa, including as a go-between for many of the loans to the Mafia by the Teamsters pension fund in the ’50s and ’60s. She was also close to Hoffa’s wife, Josephine, as was Giacalone.

A few months after the FBI installed the Giacalone bug, the Supreme Court reiterated that such surveillance was “beyond the pale.” But the FBI—confident in its backup from the top—ignored the Court’s decision. For three years, the bugs swept up the full range of conversation—not just about criminal activity but also about sex, family and health matters, political and religious opinions, and personal secrets. FBI agents transcribed the conversations with few redactions. They often summarized the transcripts in memorandums that misleadingly attributed the information to an “informant” and urged “care” in dissemination. These documents were kept in a secret file called “June” that was unknown to the public and little known within the bureau.

I have read thousands of pages of the June transcripts and memorandums from the Giacalone and Pagano bugs. The FBI gave the documents to the House Select Committee on Assassinations for its 1976–79 investigation into the Mob’s possible involvement in the killing of John F. Kennedy. Many of them are available today through the Mary Ferrell Foundation, which has a repository of documents related to JFK’s assassination. To read the June transcripts is to descend into an intimate, vulgar, gossipy, and sordid realm of unguarded conversations that took place under an assumption of privacy. Chuckie had always spoken of Jimmy and Josephine Hoffa’s relationship to each other, and to his mother and Giacalone, as one of mutual love and friendship. But the conversations picked up by the bugs reveal a darker reality.

To give one example: The bugs expose Josephine Hoffa’s mental-health challenges and ghastly struggles with addiction. Hoffa was perpetually on the road during this period—union business, criminal trials—and was callously indifferent to his wife’s condition. Pagano was given responsibility for trying to control Josephine’s alcoholism, but she grew bitter as Josephine became more and more difficult to manage. To fight her desperate loneliness, Josephine had a fiery affair with a low-level Detroit mobster. Just after it ended, Giacalone plotted with his brother, Vito, to rob the safe in Hoffa’s Washington, D.C., apartment—Hoffa was away on trial, in Tennessee—while Vito and Josephine “zoop it up.” That plot failed when Giacalone could not get into the safe. But he succeeded a few months later in robbing Hoffa’s Miami Beach apartment while Pagano and a drunken Josephine were out to dinner.

These are but a few scraps of the information about Hoffa’s circle that the FBI gleaned from the thousands of hours of June recordings. The agents learned much, much more, because Josephine, Pagano, and Giacalone spent a lot of time together—often with Chuckie—in the bugged rooms. They also communicated almost daily with Hoffa, usually through Chuckie, and often discussed, with the FBI listening in, what Hoffa was saying, thinking, and doing. Hundreds of other organized-crime figures and associates in Detroit and around the country involuntarily disclosed similarly intimate information to the FBI via illegal bugs in their homes and offices.

The bugs used on mobsters in the late 1950s and early ’60s are a mostly forgotten slice of decades of surveillance abuses. Reform finally came after the FBI’s practices leaked to the press in the mid-’60s. The first element of reform was the Justice Department’s acknowledgment of the bureau’s bugging and wiretapping, and its pledge to the Supreme Court to review pending cases for reliance on illegal surveillance.

My stepfather was an improbable beneficiary. Chuckie had been convicted in 1965 of stealing goods from a U.S. Customs warehouse in Detroit. But in 1967, after then–Solicitor General Thurgood Marshall revealed that the FBI had overheard Chuckie talking to his lawyer about his case in Giacalone’s office—a possible violation of his constitutional right to counsel—the Supreme Court vacated his conviction and ordered a new trial, assuring Chuckie a tiny place in the annals of jurisprudence.

Later that year, the Court dramatically expanded Fourth Amendment protections against electronic wiretapping. Then, in 1968, Congress passed new legislation on the use of wiretaps and bugs. Authorization now required probable cause of a crime, a judicial warrant, and other procedures, and it criminalized electronic interception in violation of these rules. It put real constraints on investigations. But it also allowed the government, for the first time, to use information gained from electronic surveillance as evidence in federal trials. Congress thus legitimized what had been legally dubious surveillance practices, and on balance empowered the executive branch. The Justice Department would later use this lawful means of surveillance as its main tool to diminish the Mob’s power.

This transformation of American surveillance law was followed, in 1975, by a comprehensive vetting of U.S. intelligence practices by a Senate select committee chaired by Senator Frank Church. The Church Committee’s final report exposed decades of electronic-surveillance abuses by the government, along with extensive evidence of illegal break-ins, mail opening, subversion campaigns, drug testing, and free-speech violations. “Governmental officials—including those whose principal duty is to enforce the law—have violated or ignored the law over long periods of time and have advocated and defended their right to break the law,” the committee concluded. In other words, the violators had backup.

The courts and Congress still had work to do after 1975. One outstanding issue was whether the president could continue to order electronic surveillance without judicial approval in national-security cases, as FDR had done in 1940. Congress addressed that issue in the 1978 Foreign Intelligence Surveillance Act (FISA), a landmark law that required electronic surveillance of suspected foreign agents to be authorized by a special court. This was the law that I would confront a quarter century later, when I began poring over cases and documents related to Stellarwind.

Stellarwind fit a familiar pattern. After 9/11, government officials faced a deadly new foe they feared they could not find and stop using traditional tools. Al-Qaeda had been empowered by technological developments, especially ones that enabled the growth of various new forms of global communications. But these and other innovations also empowered the U.S. intelligence community to surveil in new, more robust ways—especially because it had what then–CIA Director Michael Hayden described in 2006 as a “tremendous home field advantage” in intercepting global communications. In October 2001, President Bush authorized the NSA to collect targeted international telephone and email conversations of citizens and noncitizens, as well as vast amounts of telephone and email metadata. Government lawyers signed off on the program in secret, even though the collections lacked the judicial approval that FISA seemed to require.

When I arrived at the Justice Department, in October 2003, Stellarwind had been examined and reapproved by the Office of Legal Counsel every six weeks or so for two years. I inherited the responsibility of examining its legality at regular intervals. While I was doing so, I thought often about Chuckie—especially when I stumbled onto the 1967 decision that had vacated his criminal conviction.

While I was working one early-December afternoon, Jim Baker, a career government lawyer and surveillance-law expert, came by to help. Baker had not been involved in the initial approval of Stellarwind, in 2001, and when he’d found out about it, he wasn’t pleased.

“Take a look at this,” Baker said, handing me a piece of paper with scribbled signatures. It was a one-page memorandum, dated October 10, 1963, in which Attorney General Robert Kennedy had approved electronic surveillance of Martin Luther King Jr.—surveillance that yielded information the FBI would use to try to destroy King’s marriage and pressure him to abandon the civil-rights movement. At the time, I was astonished to learn that Kennedy had authorized the surveillance, without a warrant and without limit, and that he had done so based on a factually unsupported link between King and communism.

This is why we have FISA,” Baker explained, jabbing his finger at the document. He saw the King surveillance as a cautionary tale about the dangers of government corner-cutting. “If they think FISA is cumbersome or too slow, we can get rid of it,” he said.

I didn’t want to go back to those days. But I also didn’t cherish the idea of upending an intelligence program that the president had deemed vital and that the Justice Department had approved since 2001, especially given that the government at the time feared another attack. After much agonizing, I concluded in March 2004 that prior Stellarwind approvals rested on a flawed understanding of how the program worked and what the law required. After a complex analysis, I disapproved the parts of the program for which I found no plausible legal support, but I upheld the parts I thought could be supported by plausible arguments.

My decision against parts of the program provoked a now-famous constitutional clash between the Justice Department and the White House—a clash that played out in part at the foot of then–Attorney General John Ashcroft’s bed in the intensive-care unit at George Washington University Hospital. President Bush initially decided to continue Stellarwind despite the Justice Department’s objections. But in the face of threatened resignations by then–Deputy Attorney General James Comey and then–FBI Director Robert Mueller, among others (myself included), he changed his mind and accepted the department’s proposed narrowing of the program.

I was later praised by some for the steps I took in revising Stellarwind, and for standing up to the White House. Others criticized the parts of my legal opinion that approved portions of the program. With 15 years of hindsight, I don’t think I would do anything differently, given the context back then. But the critics had a point, especially regarding my reliance on the president’s war and national-security powers to skirt the statutory requirements in FISA. My argument traced its pedigree to Roosevelt’s overruling of Jackson so that Hoover could continue looking for German spies. In fact, my opinion explicitly cited the Roosevelt precedent.

Chuckie’s complaints about illegal government surveillance and Justice Department double standards turned out to be valid, and they haunted me as I did my work. Especially because the person providing backup for a secret surveillance program was now me.

My work on Stellarwind focused on how the program operated and what the law required. I barely considered the harms of undisciplined government surveillance beyond its possible illegality. But a decade later, talking with Chuckie about the Hoffa case, I did.

A lead suspect in Hoffa’s disappearance in addition to Chuckie was Anthony Giacalone. Hoffa believed he was meeting his old friend for lunch in suburban Detroit on the day he disappeared, and the FBI suspected that Giacalone masterminded the crime to prevent Hoffa from reassuming control over the Teamsters union, which the Mob had infiltrated ever more deeply in the late 1960s, while Hoffa was in prison. The government could never prove its case. So it convicted the suspects (including Giacalone and Chuckie) of crimes unrelated to the disappearance, hoping to pressure them into talking. It used leaks and misinformation toward that same end.

One government leak emerged a year after Hoffa disappeared. On August 1, 1976, the Detroit News launched a three-day front-page series based on information gleaned from the Giacalone and Pagano bugs. The stories described a supposed Detroit Mafia plot to murder Hoffa in the early ’60s; they explained the Detroit family’s inner workings; and they included information about Josephine Hoffa’s alcoholism and the Giacalones’ plot to rob Hoffa’s Washington safe. The News never mentioned that the bugs had been illegal and a gross invasion of privacy, and it never paused to note that publication of this material compounded the problem. The Hoffa story was too big, the Mafia too unsympathetic, and the details too spicy. No one was going to complain about what the newspaper had done.

Years later, I sought Chuckie’s forgiveness for my two-decade rupture, and he accepted me back into his life without qualification, rancor, or drama. Our subsequent conversations led me to question the still-prevalent conventional wisdom that he had had a hand in killing Hoffa. Chuckie’s supposed betrayal of Hoffa destroyed his reputation and, more devastating to him, stained his honor. In my own investigations, I learned that the circumstantial case against Chuckie was full of holes, that the government had not disclosed evidence that cast doubt on his guilt and implicated others, and that FBI agents and government lawyers who had long worked the case had concluded that he was innocent. Indeed, in July 2013 the government was on the verge of giving Chuckie a letter of exoneration, only to renege in order to avoid political heat.

The Detroit bugs came up one afternoon in 2015 when Chuckie and I were discussing the Hoffa disappearance at his home in Florida, where he lives today with my mother. He was sitting uncomfortably in a recliner at age 82, wearing a medical boot to protect his diabetes-damaged left foot. When I asked him about the 1976 Detroit News feature, Chuckie gave me his usual rejoinder to bad news from the government. The FBI “made all that bullshit up,” he said. “They can write down anything they want for the papers.”

This claim was often sound, since the government had, I discovered, leaked a lot of false and misleading information about Chuckie over the years, especially early in the investigation of the Hoffa disappearance. But the newspaper stories contained accurate information, if illegitimately gained. He knew it, and I knew it too: I possessed the transcripts on which the stories were based, and many more.

I had long worried that showing Chuckie the June transcripts would upset him, because they painted him and his heroes—Hoffa, Giacalone, and his mother—in a dishonorable light. They would also vividly remind him of one of the worst periods of his life, when he was for the first time trapped between what he described as his “labor side” (loyalty to Hoffa) and his “Sicilian side” (loyalty to the Mob).

In deciding whether to tell Chuckie that I possessed the June transcripts, I imagined how my beliefs about family and friends, and their relationships with one another and with me, would change if I encountered years of secret recordings of their unguarded conversations. I also tried to imagine how painful it would be to read my own unwary conversations, which would not always comport with my sentimentalized sense of self and of others. And I tried to contemplate how painful it would be to read and discuss ugly truths so many years after events in my life had played out.

In thinking about this, I came to appreciate more fully the evils inherent in the government’s bugging—the original surveillance, the archival permanence, and the periodic revelation of the content. It wasn’t just the chilling effect on Chuckie’s freedom of thought, belief, and speech—an effect that stretched back decades, to the 1950s, when he first began to suspect that he was under surveillance. It was also, more painfully, the violence against his intimate spaces and relationships, and the annihilation of the stories he told himself and the world about these spaces and relationships, and thus of his power to define and shape his life.

We tend not to take these types of harm seriously when we consider bugs planted to gather evidence against Mob figures. We tend to think such people don’t deserve privacy, because they belong to an organization whose mission is to violently defy the legal system. Even the Church Committee, which railed against the abuse of government surveillance, barely mentioned the massive surveillance program against the Mob, although that program was more clearly illegal than most of the other activities the committee condemned.

But the privacy harms are the same whether the target is guilty or innocent, bad or good. The Fourth Amendment of the Constitution accepts “reasonable” intrusions on private spaces in the name of law enforcement and national security. Yet harms remain present, a trade-off even for lawful government surveillance, which the Detroit bugs were not.

My qualms did not prevent me, that afternoon in Florida, from telling Chuckie that I had the transcripts on which the leaks were based. He asked to see them. I gave him one that showed that his mother had plotted with Giacalone to rob Hoffa.

Chuckie read with a blank expression for two minutes. Then he winced as if he had broken a tooth, and threw the papers across the room. “I don’t want to read this shit,” he said, “and I don’t want to talk about it.”

I was not surprised by this reaction. Chuckie was confronting evidence that shattered his constructed worldview. Practically everyone on the tapes viewed the powerful Hoffa in crass transactional terms. They wanted a loan, or help with a legal problem, or his money, or more of his time. Or they wanted to push him aside, or take advantage of him, or even knock him off. Hoffa was often treated with disrespect or disdain.

But not by Chuckie. In the thousands of pages of transcripts I read, no one displayed more affection for Hoffa than Chuckie did. In 1963, just after Hoffa was indicted on charges that would eventually send him to prison, Chuckie complained angrily to his mother that some members of the Teamsters’ executive board were jockeying to force Hoffa out. “They don’t care about Hoffa; they don’t care if Hoffa lives or dies,” Chuckie lamented to his mother in her apartment, at 6:04 p.m. on Thursday, June 13, 1963, as FBI agent Gerald R. McVittie illegally listened in.

Despite the secrecy of illegal government surveillance in the early 1960s, rumors of government snooping abounded at the time and sparked feverish concern about “Big Brother.” Newspapers and magazines were filled with stories about miniature microphone devices, radio transmitters, and other examples of what Supreme Court Justice Potter Stewart described in 1961 as “frightening paraphernalia which the vaunted marvels of an electronic age may visit upon human society.”

In this milieu, Jimmy Hoffa believed that the FBI “tapped his phone, opened his mail, and beamed electronic listening devices on him from half a mile away, aided by invisible powder they had rubbed onto his clothes,” as Ralph and Estelle James recounted in their 1965 book about Hoffa. Whether the government illegally surveilled Hoffa himself (as opposed to just his associates) remains a contested historical question. But until the day he went to jail, in March 1967, Hoffa never stopped speaking publicly about the dangers of surveillance.

In the early 1960s, the paranoid Hoffa asked Chuckie to buy thousands of copies of George Orwell’s 1984 and distribute them to union locals around the country. “Some of these poor guys, the only thing they knew was how to drive a truck or work at a warehouse,” Chuckie told me. “They didn’t have the knowledge of the electronic shit. Mr. Hoffa wanted them to read that book and said that this is what’s going to happen to not only us but to everybody—and exactly what he’s predicted has happened.”

Chuckie is basically right about Hoffa’s prediction. But there are several differences between today and the era in which Chuckie was secretly surveilled.

First, today’s threats to privacy come not only from the government but also from the private sector—from Facebook, Google, Amazon, and the hundreds of other platforms, apps, and aggregators to which we daily turn over our most intimate secrets.

Second, the government’s surveillance power has grown unfathomably since the 1960s. The “frightening paraphernalia” from six decades ago are toys compared with the redoubtable tools that allow the government to watch and record our movements and communications, and that enable it to store almost limitless amounts of data on its own or to piggyback on the masses of data that we volunteer to private firms.

And third, Congress has ratified and legitimated what were once legally tenuous surveillance techniques. It did so after the executive branch convinced legislators that the techniques were necessary for law enforcement and national security, but it imposed various legal constraints on their use. Congress had taken such steps in the late 1960s for domestic criminal investigations. It did basically the same for foreign threats, broadly conceived, first in the FISA law of 1978; then again in 2008, following public revelations about Stellarwind. Congress acted a few times when Barack Obama was president—including after the intense controversy sparked by the then–NSA contractor Edward Snowden’s 2013 leak of thousands of highly classified government documents about secret surveillance practices—and acted most recently in January 2018, a year into Donald Trump’s presidency.

The result of these developments is yet another “new normal” in which the government is constrained in certain respects but citizens are far more exposed to lawful government surveillance than before. This latest new normal, like earlier ones, will not prove stable. Technology develops apace. Sensors will soon be placed on practically everything. Facial-recognition and other biometric-identification techniques, along with drone and satellite surveillance, will become commonplace and extraordinarily discerning. Data-mining and pattern-detection tools, enhanced by artificial intelligence, will grow ever more powerful.

If history is a guide, the government will perceive a security advantage in using these and other tools in new ways to watch us and to predict and preempt our behavior. It will sometimes deploy the tools in secret, despite legal impediments, in order to prevent calamities threatened by new foes, many of whom will themselves be empowered by technological change. We will be outraged by the seeming excess when we find out. But the outrage will dissipate. Except in the most extreme cases of abuse or fecklessness, Congress will legalize the surveillance practice on the condition, mainly, of new procedural restraints. And we will adjust to our more naked selves.

This is a depressing conclusion for many, but it is an inevitable one. The executive branch does what it thinks it must, including conduct robust surveillance, to meet our demands for safety. The technology of surveillance races ahead of the law of surveillance, which tries to catch up in spurts, and often does an admirable job of curtailing old abuses. But the law cannot eliminate ever-growing threats, and security is elemental. And so the cycle recurs.

This essay is adapted from Jack Goldsmith’s new book, In Hoffa’s Shadow: A Stepfather, a Disappearance in Detroit, and My Search for the Truth. It appears in the November 2019 print edition with the headline “Jimmy Hoffa, My Stepfather, and Me.”