ONE EVENING IN EARLY DECEMBER 2003, I found myself alone in a brightly lit, cavernous office on the fifth floor of the United States Department of Justice, reading a stack of Supreme Court decisions about the Fourth Amendment’s prohibition on unreasonable searches and seizures. At the time I was serving as the assistant attorney general in charge of the Office of Legal Counsel, a position that made me a senior legal advisor to the attorney general and the president. A few weeks earlier, I had concluded that President George W. Bush’s secret two-year-old warrantless surveillance program, Stellarwind, was shot through with legal problems. I was working late that night because I was under a deadline to figure out which parts of the program might be saved.
The stakes were enormous. The program’s operator, the National Security Agency, was picking up what its director would later describe as a “massive amount of chatter” about al-Qaeda plans for “catastrophic” operations in the Washington, D.C., area. I was certainly anxious based on the threat reports I was reading. And yet I increasingly believed that large parts of the program could not be squared with congressional restrictions on domestic surveillance—a conclusion I feared would risk lives and imply that hundreds of executive branch officials, including the president and the attorney general, had committed crimes for years.
My thoughts that stressful December evening began with a crisis about national security and presidential power but soon veered to a different turbulent period of my life. One of the cases in my “to-read” pile was a 1967 Supreme Court decision, Berger v. New York, that restricted the government’s use of electronic bugs to capture private conversations by stealth. As my tired eyes reached the end of the opinion, two citations leapt off the page like ghosts: “O’Brien v. United States, 386 U.S. 345 (1967); Hoffa v. United States, 387 U.S. 231 (1967).”
I looked up, incredulous. Neither case was in my stack. So I turned to my computer and printed them out.
The Hoffa case involved the pension fraud conviction of James Riddle Hoffa, the autocratic leader of the International Brotherhood of Teamsters who would later vanish, on July 30, 1975, in what remains one of the greatest unsolved crimes in American history. The O’Brien decision concerned the conviction of Charles “Chuckie” O’Brien, also a Teamsters official, for stealing a marble statue of St. Theresa from a U.S. Customs warehouse in the Detroit Harbor Terminal. The Supreme Court vacated both convictions so that lower courts could determine if the government had eavesdropped on Hoffa and O’Brien in possible violation of a new governmental policy and developing Supreme Court jurisprudence. The Hoffa and O’Brien cases were important in their day, but by 2003 had become mere footnotes in the long struggle for legal control over electronic surveillance. That’s why they weren’t in my stack.
After reading the decisions, I immediately saw their connection to each other, and to me. In the 1950s and 1960s, Jimmy Hoffa was the nation’s best-known and most feared labor leader at a time when unions were consequential forces in American life. Chuckie O’Brien met Hoffa at age nine and later served as his most intimate aide for more than two decades. O’Brien helped Hoffa bulldoze his way to the presidency of the Teamsters. He was Hoffa’s trusted messenger to organized crime figures around the country, and was by his side during his seven-year battle with Bobby Kennedy that ultimately sent Hoffa to prison. O’Brien escorted Hoffa to his jailers in March 1967, helped secure Richard Nixon’s commutation of Hoffa’s sentence in December 1971, and stuck by Hoffa as he struggled to regain control of the Teamsters during his post-prison years.
But in 1974, he and Hoffa had a falling-out. They barely spoke in the eight months before Hoffa disappeared. Soon after Hoffa vanished, O’Brien became a leading suspect. He was closely connected to the men suspected of organizing the crime. Based on a slew of circumstantial evidence, the FBI quickly concluded that O’Brien picked up Hoffa and drove him to his death.
I knew this history well because Chuckie O’Brien is my stepfather. His relationship with my mother, Brenda, was one of the reasons he broke with Hoffa in 1974. I was a pimply twelve-year-old in braces when Chuckie and Brenda wed in Memphis, Tennessee, on June 16, 1975, forty-four days before Hoffa vanished. Ever since Hoffa disappeared, my life has been colored by the changing implications of my relationship to the labor icon, and to Chuckie, whom Hoffa treated as his son, and whom I knew as “Dad.”
* * *
CHUCKIE AND I were very close when I was a teenager, during the height of the Hoffa maelstrom. He was a great father despite his lack of education, the oppressive FBI investigation, and an angry, excessive pride. Chuckie smothered me in love that he never received from his father, and taught me right from wrong even though he had trouble distinguishing the two in his own life. In high school I idolized Chuckie. When I set out on my professional path in law school, however, I renounced Chuckie out of apprehension about his impact on my life and my career. We had barely spoken for two decades by the time of my service in the Justice Department.
I left government in 2004 to become a professor at Harvard Law School, and soon afterward Chuckie and I patched up and once again grew very close. During the next eight years, we often discussed his trying experiences with Jimmy Hoffa and the government juggernaut that since 1975 had sought to pin the disappearance on him. Chuckie had always denied any involvement in Hoffa’s death. Over the decades he had been consumed with resentment as the government hounded him and tarnished his reputation through incriminating leaks to the press based on evidence that Chuckie was never able to examine or contest. He watched with bitter frustration as hundreds of newspaper stories and nearly a dozen books were published with supposed insider revelations about the crime and his role in it.
“What’s bothered me my whole life,” Chuckie once told me, “is that the government through their devious assholes in the Justice Department turned me into something worse than Al Capone.” Yet every time Chuckie tried to explain his side of things on television and radio, he ended up looking worse for the effort.
My conversations with Chuckie made clear why he had been such a poor advocate for himself. He wasn’t eloquent and his explanations about his role in Hoffa’s disappearance sometimes seemed guarded, self-serving, or mendacious. This did not surprise me. Since I was twelve I had often experienced, and frequently laughed at, Chuckie’s tendency to hedge or fib. The FBI viewed it as a reason not to believe Chuckie’s alibi on the day of Hoffa’s disappearance. In a 1976 memorandum analyzing the case, the Bureau noted, “O’BRIEN is described by even his closest friends as a pathological liar.”
The more Chuckie and I talked, the more I came to understand that his adversarial relationship with the truth was influenced by his commitment to Omertà, the Sicilian code of silence that he embraced at a young age. Chuckie had a lifelong hatred of rats—people who broke the code and betrayed their honor—and he was alive to speak to me only because he was adept at keeping his mouth shut about certain things. One coping mechanism to ensure that he didn’t speak out of school was to shade the truth. “I never told anybody what was right,” Chuckie once told me, trying to be truthful. “I always used what I had to use to divert it.”
The conversations with Chuckie drew me into a thicket of ambiguity—about Hoffa’s disappearance and much more—in which fact and fiction were hard to distinguish. As I tried to make sense of Chuckie’s stories and began to study the public evidence against him, I started to doubt that he was involved in Hoffa’s disappearance. But I also developed an inkling that Chuckie knew much more than he had told me—and even that he might know the whole story about the disappearance.
“Why don’t I write a book about this?” I asked at the end of one of our chats, in early 2012. I was drawn by the mystery of the disappearance, by Chuckie’s complicated relationship with the enigmatic Hoffa, and by the fascinating characters that Hoffa and Chuckie had bumped into during their quarter of a century together. I also believed that no matter what came of the project, I could give Chuckie a fairer shake than history had thus far. And I hoped that doing so might make up, at least a bit, for our long estrangement.
I assumed Chuckie would jump at my offer, since he was so distraught about his reputation and legacy. “It pisses me off that I’m gonna die, go away, and my grandchildren will never know nothing—the good things that I’ve always done for labor and everyone else,” he had told me the day before.
But Chuckie didn’t jump at my offer. “I gotta think about it,” he said after a long silence. He finally assented after a few days of reflection because, as he told me, he was bitter about what he viewed as the government’s crooked hounding of Hoffa and him and his Italian friends, since the 1950s. He also hoped that I could use my legal training, academic skills, and Justice Department connections—none of which he really understood—to exonerate him from the charge that he was involved in Hoffa’s death. I doubted I could do this. But I pledged to him that I would try my best to tell his story well, on one condition.
“You have to tell me the truth.”
* * *
I HAD MANY reasons to think the truth would be elusive, and not just because of Chuckie’s evasions. As one FBI agent who worked the case in the 1970s told me, much of what the public knows about Jimmy Hoffa’s disappearance is “science fiction.” For forty-five years, public knowledge has been shaped by unreliable informants, tendentious government leaks, credulous journalists, or aging (and now-dead) mob figures looking to make a buck. Book after book and article after article has provided different theories of Hoffa’s death, almost all of which involve Chuckie. And yet there is still not one single piece of direct evidence about what happened to Hoffa on the afternoon of July 30, 1975.
It is apt that my main source for trying to solve this perfect crime is an unreliable chronicler with a stake in the outcome of the events he lived through. For several years I pushed Chuckie in hundreds of hours of conversations—as a son wanting to learn the family history; as a scholar interviewing the person most closely connected to the Hoffa disappearance and its leading characters; and as a cross-examining prosecutor testing the witness’s credibility. Our conversations were often maddening, comical, or both. Chuckie inhabits a different linguistic and conceptual universe than I, and rarely provided the direct or intellectually tidy answers I sought. He also hesitated, at first, to discuss some of the legally dubious episodes in his life. Over time, he grew more comfortable in our discussions. He did not “tell all,” but he did reveal a great deal of new and fascinating information about important historical events that he lived through, including the Hoffa disappearance.
I also spent a great deal of time trying to corroborate or correct what Chuckie told me. I dug deeply into thousands of pages of unpublished or unexplored government records, including thousands of pages of transcripts from illegal bugs that recorded Chuckie, his mother, and Detroit crime family members in the early 1960s. I did research in archives in more than a dozen libraries. And I interviewed dozens of people, including journalists and historians who are experts on Hoffa and the Teamsters, the four primary FBI agents originally assigned to the Hoffa disappearance, and a dozen other investigators and prosecutors who worked the case thereafter—including those currently assigned to it.
My investigation did not uncover the specifics of what happened to Jimmy Hoffa on July 30, 1975, but it did help me to figure out why the forty-five-year-old conventional wisdom that Chuckie was involved in Hoffa’s disappearance is almost certainly wrong. Despite my acknowledged interests, I believe the pages that follow cut through decades of obfuscation and set forth the most objective, fair-minded, and revealing assessment of Hoffa’s disappearance to date—one that sheds authentic light on the case and the era in which it happened.
This book started off as an effort to understand Chuckie’s role in Hoffa’s disappearance, but it grew to be about much more. It is about how a hapless blabbermouth with famously terrible judgment served as a close aide to both Hoffa and a top Detroit mob figure, both of whom trusted him with their most intimate secrets. It is about how an uneducated serial lawbreaker with mob values nourished his vulnerable stepson at a crucial stage in his life to set him on a path that led to the Justice Department and Harvard Law School. It’s about Chuckie’s life, and mine, in the forty-five-year vortex of the Hoffa disappearance, and my changing thoughts, over the course of my life, about these events. And it is about what I learned about truth-telling, honor and pride, and paternal and filial love and treachery—from Chuckie’s tragic ensnarement between two ruthless father figures and implacable government investigators, and from my relationship with Chuckie.
The book is also about the complex legacy that Jimmy Hoffa bequeathed to the American labor movement and American justice. Hoffa is remembered today as a union autocrat who broke the law and worked closely with organized crime. That’s true. But as Chuckie taught me, Hoffa also protected the Teamsters from the mob, and his actions were motivated to help workers, which he did with wild success. Hoffa was a labor-organizing genius who leveraged his union’s power to lift many hundreds of thousands of people from poverty to the middle class. He was on the verge of even greater labor accomplishments when Robert Kennedy’s seven-year assault destroyed him in a manner that was more responsible than has been appreciated for the steady decline in union power ever since. Kennedy’s investigations of Hoffa involved excesses approaching criminality and an expansion of the surveillance state for which no one in the government was ever held accountable. They also had an improbable, reverberating impact on subsequent American legal culture, spanning from progressive surveillance reform in the late 1960s to the post-2001 “war on terrorism.”
My conversations with Chuckie helped me to understand all of this, and altered my views on matters as far afield as unions, government surveillance, and the basic fairness of American institutions. They also helped me to better understand Hoffa’s—and Chuckie’s—worldview. “My ethics are very simple,” Hoffa once explained. “Live and let live, and those who try to destroy you, make it your business to see that they don’t and that they have problems.” This philosophy worked for the decades when Hoffa had more power than his many adversaries. In the end, after he lost that power, Hoffa was killed.
Chuckie was raised on and lived by Hoffa’s ethics, which informed all our conversations. He also lived by Omertà, which was also present in our conversations, and which in the end clashed with his commitments to Hoffa. I often pressed Chuckie to reconcile his harsh moralistic condemnation of law enforcement abuses against Hoffa and organized crime with his own tales of unregretted violence and frequent lawbreaking that both Hoffa and Omertà seemed to invite. “It’s maybe not ethical in a way you understand,” he told me. “But we had to do things to win. If we didn’t do it, they would do it to us. And that’s just the way life was.”
Chuckie never persuaded me on this point. But on plenty of others, he did. The uneducated union man, it turned out, had a lot to teach the professor.
What follows is an account of what I learned.
Copyright © 2019 by Jack Goldsmith
Afterword copyright © 2020 by Jack Goldsmith