In In Hoffa’s Shadow, Jack Goldsmith, a professor at Harvard Law School, tells the flabbergasting story of his relationship with his father—actually, his stepfather—who was a close associate of various mobsters and of Teamster president Jimmy Hoffa, and who was long believed by law enforcement to have been involved in Hoffa’s murder and disappearance in 1975.

Goldsmith begins his narrative with his work in the Justice Department after 9/11, serving as chief of the Office of Legal Counsel (OLC), the pivotal unit that serves as counsel to the U.S. government as a whole, deciding what is lawful for the government to do and what is not. A critical task that fell to Goldsmith was reviewing decisions taken by his OLC predecessor, which had authorized warrantless mass surveillance and torture. Goldsmith found that the legal reasoning in these decisions was seriously flawed and he set out to withdraw them, with the effect of terminating programs that the Bush Administration believed were vital to the successful prosecution of the war on terror. Goldsmith told the story of his epic bureaucratic battles in a previous book, The Terror Presidency (which I reviewed in Commentary in 2008 when it came out). In Hoffa’s Shadow adds an entirely new and deeply personal universe to the story told in that volume.

It was in the course of reviewing the National Security Agency’s warrantless surveillance program that Goldsmith, “incredulous,” came upon an obscure Supreme Court decision, O’Brien v. United States. The O’Brien in question was Charles “Chuckie” O’Brien, his stepfather, who had been convicted of a minor theft—he stole a statue of St. Theresa from a U.S. customs warehouse—but had been the target of illicit FBI surveillance in the early 1960s, and whose conviction was later vacated by the Supreme Court. The discovery of this case set in motion a chain of thoughts and feelings that led Goldsmith to retrace his own life path.

O’Brien had come into Goldsmith’s life in 1975 when he was 12 years old, when his mother, a woman of “fragile mental health,” married him, her third husband, just weeks before Hoffa’s disappearance. Whatever his mobster affiliations, Chuckie had extraordinary personal qualities, and he “smothered” young Jack with love. “All I knew,” recollects Goldsmith, “was that a gregarious brown-eyed man with a potbelly, long dark sideburns, an inviting smile, and the biggest forearms I had ever seen had suddenly glommed on to me with love and attention.” Goldsmith came to idolize his new father, calling him a “large, stable, affectionate presence in my life,” and eventually took his name, becoming Jack O’Brien. “Chuckie was my third father,” writes Goldsmith, “and my best.”

But as Goldsmith matured, hero worship turned into something else. In the middle of his junior year in high school, Chuckie, under microscopic scrutiny by law enforcement, was convicted and sent to prison on two minor charges, including inflating his income on a bank loan application. The experience left Jack “devastated.” By the time Goldsmith entered college, he began reading about Hoffa’s disappearance and the Mafia, including about figures in it that he had come to know personally through his relationship with Chuckie. Not only did he begin to question Chuckie’s associations, he became personally embarrassed by his uncouth and uneducated manner. “I soon began to show open disrespect to the man I once idolized,” writes Goldsmith.

It did not help that in going to law school and then embarking on a legal career, Goldsmith feared (not without reason) that Chuckie’s ties to the murdered Hoffa and the Mafia might prove to be an impediment to professional success. The distancing continued and culminated in an act of callous cruelty. Jack O’Brien turned his surname back to Goldsmith, wounding his stepfather to the quick. He then severed relations with him, having almost nothing to do with him for some 20 years.

The experience of having children of his own awakened in Jack a feeling of profound remorse about his treatment of the man he had loved as a boy. After leaving the Justice Department in 2004, Goldsmith managed to patch things up with Chuckie. Engaging in intense conversations with his now elderly stepfather about his past, Goldsmith set out to find out the truth about Hoffa’s disappearance, not only relentlessly probing the reluctant Chuckie, but also scouring all available (and many hitherto unavailable) documents and interviewing every living player involved in the case, including the FBI agents who failed to solve it.

Although Goldsmith does not crack the riddle of one of America’s greatest unsolved murders, he does illuminate in riveting detail the circumstances surrounding it. He goes a great distance to refuting the most common theory: that Chuckie had a hand in it. (Martin Scorsese’s The Irishman is the most recent rendition of the incident.) Along the way, readers are given an education in the uses and abuses of the laws governing surveillance, in the intricate relationship between organized crime and the Teamsters Union, a portrait of Hoffa himself, and an account of the cruelty of the U.S. government in pursuing Chuckie, and of refusing to clear him of suspicion, even when the evidence became clear that he was uninvolved.

The most affecting part of the volume is Goldsmith’s checkered portrait of his stepfather, to whom the book is dedicated (and who, sadly, passed away yesterday, February 13, 2020). One feels Goldsmith’s pangs of regret about his own past conduct and his deep love for the man who adopted him. But at the same time, the book is unsparing in showing Chuckie’s outsized warts.

Thus, Chuckie is painted as a chronic liar, an “unreliable chronicler,” given to constant evasions and striving to adhere to the never-tell ethos of the mob: “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 was also professionally incompetent. Though aspiring to play a bigger role in the Teamsters union, Hoffa never gave him the opportunity, in no small measure because Chuckie was seen by his Teamster associates as buffoonishly inept.

As Goldsmith neared completion of his volume, he gave the unpublished manuscript to Chuckie to read and to comment upon, even as it contained, in no small part, an unflattering portrait of the man. “I prayed,” writes Goldsmith, “that he would see the book as an act of love. I also hoped that he would think I portrayed him fairly and honorably, and would appreciate my efforts to clear his name. But I worried, and told him, that he might not like some things in the manuscript.”

“I read every word. You wrote a great book,” was Chuckie’s comment about the book. Goldsmith calls this a “noble lie,” writing, in one of the more poignant passages in a volume laden with powerfully understated emotion, “I doubt that Chuckie read every word. I saw him frown and then scowl two days earlier at about the place in the book where I described how others viewed him in the Teamsters. He barely dipped into the manuscript after that—at least when I was watching. I wonder if he even looked at the last half.”

Causing yet more pain to the man he loved, Goldsmith reveals himself to be a ruthless seeker and teller of the truth, which includes telling uncomfortable truths, including about himself and his past conduct. It is a deeply admirable quality that shines throughout the book, but the writerly courage on display inevitably exacts a human cost at the most personal level.

In Hoffa’s Shadow comes adorned with blurbs that extol it in extravagant terms. Amy Chua calls the book “a masterpiece and a page-turner. I couldn’t put it down. Brilliant, suspenseful, and deeply moving, it offers a personal view of one of the greatest unsolved crimes in American history.” Bill Buford writes that it is “A thrilling unputdownable story that takes on big subjects—injustice, love, loss, truth, power, murder—and addresses them in sentences of beauty and clarity informed by deep thought and feeling.”

I would subtract not a word from these glowing encomiums and add only that Goldsmith’s The Terror Presidency, a tale of fearlessness in public service, was one of the very best non-fiction books I read in the first decade of this century. In Hoffa’s Shadow, a display of courage of a very different kind, is the single best non-fiction book I’ve read from the century’s second decade. Goldsmith has added a remarkable literary-autobiographical-historical achievement to his name.