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In Hoffa's Shadow: A Stepfather, a Disappearance in Detroit, and My Search for the Truth

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"In Hoffa’s Shadow is compulsively readable, deeply affecting, and truly groundbreaking in its re-examination of the Hoffa case . . . a monumental achievement." —James Rosen, The Wall Street Journal

As a young man, Jack Goldsmith revered his stepfather, longtime Jimmy Hoffa associate Chuckie O’Brien. But as he grew older and pursued a career in law and government, he came to doubt and distance himself from the man long suspected by the FBI of perpetrating Hoffa’s disappearance on behalf of the mob. It was only years later, when Goldsmith was serving as assistant attorney general in the George W. Bush administration and questioning its misuse of surveillance and other powers, that he began to reconsider his stepfather, and to understand Hoffa’s true legacy.

In Hoffa’s Shadow tells the moving story of how Goldsmith reunited with the stepfather he’d disowned and then set out to unravel one of the twentieth century’s most persistent mysteries and Chuckie’s role in it. Along the way, Goldsmith explores Hoffa’s rise and fall and why the golden age of blue-collar America came to an end, while also casting new light on the century-old surveillance state, the architects of Hoffa’s disappearance, and the heartrending complexities of love and loyalty.

376 pages, Kindle Edition

First published September 24, 2019

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About the author

Jack L. Goldsmith

31 books32 followers
Jack Landman Goldsmith III (born September 26, 1962) is a Harvard Law School professor who has written extensively in the field of international law, civil procedure, cyber law, and national security law. He has been "widely considered one of the brightest stars in the conservative legal firmament."

Goldsmith was born in 1962 in Memphis, Tennessee. His stepfather, Charles "Chuckie" O'Brien, is widely believed to have played a role in the disappearance of Jimmy Hoffa.[6] Goldsmith graduated from Pine Crest School in 1980.

He was a law professor at the University of Chicago when in 2002, he joined the Bush administration as legal adviser to the General Counsel of the Department of Defense. In October 2003 he was appointed as an United States Assistant Attorney General, leading the Office of Legal Counsel in the Department of Justice under Attorney General John Ashcroft and Deputy Attorney General James Comey. He resigned in July 2004. He wrote a book about his experiences there called The Terror Presidency (2007).

Goldsmith graduated from Washington & Lee University with a Bachelor of Arts summa cum laude in 1984. He earned a second B.A. with first class honours, from Oxford University, in 1986, a J.D. from Yale Law School, in 1989, an M.A. from Oxford (which is not a separate degree, but an upgrading of the BA), in 1991, and a diploma from the Hague Academy of International Law in 1992. He clerked for Judge J. Harvie Wilkinson III on the United States Court of Appeals for the Fourth Circuit from 1989 to 1990, and for Justice Anthony Kennedy of the Supreme Court of the United States from 1990 to 1991.

He was a professor at the University of Virginia Law School before going to the University of Chicago Law School. He was working there in 2002 when he first joined the administration of President George W. Bush as a political appointee.

In 2007, Goldsmith published The Terror Presidency, a memoir about his work in the Bush administration and his thoughts on the legal opinions which were promulgated by the Department of Justice in the war on terror. His discussion covers the definition of torture, the applicability of the Geneva Conventions to the war on terror and the Iraq War, the detention and trials of suspected terrorists at Guantanamo Bay and elsewhere, and wiretapping laws. He is largely sympathetic to the concerns of the Bush administration's terrorism policies. He believed that fear of another attack drove the administration to its focus on the hard power of prerogative, rather than the soft power of persuasion. In the end, he believed the fear and concentration on hard power were counterproductive, both in the war on terror and in the extension of effective executive authority.

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Profile Image for Max.
357 reviews525 followers
July 11, 2022
Jack Goldsmith writes a memoir focused on his relationship with his stepfather, Charles “Chuckie” O’Brien. Chuckie, a close associate of Jimmie Hoffa, has long been suspected of being involved in the disappearance of the powerful Teamster leader. Hoffa’s disappearance in 1975 remains an unsolved mystery but the common assumption is that the Mafia murdered him. There are three main themes in the book. First is the personal story of Goldsmith’s relationship with Chuckie and how the Hoffa case impacted Chuckie, the author and his mother. The second is Goldsmith’s case that Chuckie was not involved in Hoffa’s disappearance. The third is the abuse of power by the government beginning with Robert Kennedy, then Nixon and finally the Bush administration. Chuckie believed the government was as corrupt as the Teamsters and Goldsmith details abuses related to Hoffa at the hands of RFK and outright corruption under Nixon. Goldsmith then personally sees the same abuses in a different context as Assistant Attorney General in the Bush administration. The book shows how warrantless government surveillance has been used repeatedly. While Chuckie’s inside view of Hoffa and his disappearance was interesting, the theme that resonated with me was the misuse of power from RFK to Bush. My notes follow.

Chuckie was nine years old in 1943 when he met Hoffa. Sylvia, his mother of Sicilian heritage, would drop him off to spend weekends with Hoffa and his two children. Hoffa and Chuckie were very close throughout their lives and many thought incorrectly that Chuckie was Hoffa’s child. The nine-year-old Chuckie also met organized crime figure Anthony Giacalone who Chuckie called uncle Tony. Sylvia kept books for his gambling operation. She introduced Hoffa to her mob connections and became close friends with Hoffa’s wife, Josephine. Giacalone became a long time Hoffa friend and prime suspect in his disappearance. But when Goldsmith’s mother married Chuckie in 1975, 44 days before Hoffa disappeared, all the twelve-year-old Goldsmith knew was that he had found the father who finally loved him.

Goldsmith adored Chuckie, but when he went off to college and decided to go to law school, he turned his back on his stepfather hurting him deeply. Goldsmith’s new polished image didn’t fit with Chuckies’ rough and tumble Teamster persona. Chuckie said that the police and FBI had always harassed him for political reasons. Goldsmith dismissed those arguments and after graduating from law school wanted to work in law enforcement. He ended up working for the Justice Department and during the George W. Bush administration was confirmed in 2003 by the Senate to be United States Assistant Attorney General for the Office of Legal Counsel. The OLC advises the president, executive agencies and the attorney general with respect to the legality of pending legislation, executive orders and other matters.

In 2004 Goldsmith found himself at odds with the Bush administration’s legal justifications for enhanced interrogations and warrantless wiretaps and pushed back. He and James Comey advised Attorney General John Ashcroft to declare Bush’s warrantless wiretap program illegal which he did. Goldsmith was with Ashcroft at his bedside in intensive care when administration officials showed up pressing Ashcroft to change his mind. In 2004 Goldsmith resigned. The experience changed his mind about his stepfather. He saw that the DOJ after 9-11 mirrored what Chuckie told him about the 1960s Kennedy DOJ. Now, a parent himself, Goldsmith reconciled with Chuckie and apologized to him. Chuckie was ecstatic and said no apology was needed, that he understood why his son did what he did.

Chuckie was well aware of the Teamsters’ mob ties, but he didn’t think the police, FBI or DOJ were any better. In the 1930s when employers hired mob thugs to beat up strikers and labor organizers, the police looked the other way. When the Teamsters resorted to the same tactic, the police were all over them. As Hoffa later put it, “I’ve never been able to understand why the finger is pointed at us in the Teamsters - and only at us – that we knew mobsters and hoodlums. Mob people are known by employers and employers’ associations much better than we ever knew them and employers were always the first to employ them.”

Hoffa helped himself to money on the side, but pay and working conditions for union members improved so much, they didn’t complain. Hoffa won great contracts for the Teamsters. In 1964 Hoffa got the first national trucking contract. It helped the trucking companies scale up as well. Making the Teamsters an effective national organization meant working with the Mafia which controlled important locals in New York. The relationship was one of each side making itself available for favors from the other. When there was a disagreement, Chuckie’s mother, Sylvia Pagano, would often step in to resolve the dispute. Chuckie was always by Hoffa’s side as a driver and loyal assistant who took care of small details and was trusted by both sides to carry messages and money and keep his mouth shut.

In the fifties and sixties Robert Kennedy went after Hoffa with a vendetta, first as counsel to the Senate Labor Rackets Committee from 1957-9 and later as Attorney General 1961-4. Hoffa was a criminal skimming union funds and making loans with Union money to Mafia businesses. But RFK’s crusade had bigger consequences than the eventual conviction of Hoffa. It was in RFK’s political interest to show he could take on the mob, but he ended up demonizing all of labor, a perception it never recovered from. Goldsmith, thinking of his own experience with the misuse of power, saw unsettling precedents in the way RFK went after Hoffa. RFK had Hoover and the FBI at his disposal to relentlessly surveil anybody suspicious. As Attorney General under his brother, RFK assembled his “Hoffa Squad”. RFK had one of his old law professors named IRS commissioner. At RFK’s direction, the IRS gave RFK’s former congressional committee any records they asked for including those related to information from warrantless wiretapping and bugging which rapidly grew under RFK. Anyone associated with Hoffa including his attorneys were targeted. RFK released carefully crafted information to the press to shape public opinion. Ironically after Hoffa was sent to jail in 1967, mob influence over the teamsters greatly increased. Hoffa could stand up to the mob to protect the Teamsters’ interests, his successor couldn’t. In 1963 RFK even signed off on FBI warrantless technical surveillance of Martin Luther King citing “possible communist influence.”

After 9-11, Attorney General John Ashcroft, who was well aware of RFK’s “Get Hoffa” campaign, adopted the RFK model to go after terrorists. He used the immigration laws and designated suspicious people “material witnesses” to hold them. He authorized aggressive interrogations and warrantless mass phone, email, internet use and financial transaction metadata collection under a Bush program called Stellarwind. Goldsmith was an Assistant Attorney General from 2003-4 under Ashcroft. Goldsmith had written memos seeming to approve of Stellarwind, although he says he was putting constraints on it. He states that he together with James Comey convinced Ashcroft not to renew the authorization for Stellarwind in 2004. Goldsmith recalls the remarkable visit by Bush’s White House counsel Alberto Gonzalez, Chief of Staff Andrew Card, and VP counsel David Addington to Ashcroft’s hospital bed in intensive care. Ashcroft was heavily sedated and just out of serious surgery for an inflamed pancreas. Ashcroft was pressured to reauthorize Stellarwind right there. But he refused to sign off despite Addington screaming at him demanding he do so. Still, Bush dropped the program only after Ashcroft, Comey and Robert Mueller threatened to resign. Goldsmith was there with Ashcroft in the hospital room and the experience was a profound one for him. He thought about what Chuckie had always said about the feds making their own rules particularly employing secret government surveillance without restrictions. Now, he found himself facing the same thing in the Bush administration.

Hoffa went to jail in 1967 sentenced to thirteen years for bribery and fraud. Hoffa selected Frank Fitzsimmons to run the Teamsters in his absence. Fitzsimmons established a cozy relationship with the Nixon administration and became an ardent vocal supporter. But rank and file teamsters still revered Hoffa. Nixon’s political calculation running up to the 1972 election was to secure those Teamster votes by commuting Hoffa’s sentence and he did in 1971. But Nixon was happy with Fitzsimmons and didn’t want Hoffa to be running the Teamsters again so a condition attached to the commutation was he not hold any Teamsters’ office. To get out of jail Hoffa agreed to the condition and to pay Nixon $1 million through John Mitchell who would resign as Attorney General in 1972 to become Nixon’s campaign chairman. Chuckie told Goldsmith that he delivered the money in December 1971. There was an interesting conversation recorded on the Nixon tapes December 8, 1971 just 30 minutes before the commutation was issued. Nixon references an arrangement between AG Mitchell and Fitzsimmons saying that Fitzsimmons should “play our game now” and told Chuck Colson to tell Fitzsimmons that Nixon “wants it done the right way”. Nixon went on saying Fitzsimmons should “tell Mitchell everything he wants and that Mitchell will do it.” Goldsmith believes the conversation which used code words referred to a cash for commutation deal. Fitzsimmons told Chuckie that Hoffa’s commutation would cost $1 million. Chuckie that December picked up a briefcase in Fitzsimmons’ office with the $1 million and took it to a room in the Madison Hotel in DC at 7PM. Chuckie handed it over in a dark room. It’s Chuckie who tells Goldsmith that this was Hoffa’s money, not the Teamsters. To Chuckie’s point, were the Teamsters any more corrupt than the government?

Hoffa was released from prison December 23, 1971. He was hellbent on running the Teamsters again, but the condition and a self-serving relationship between Fitzsimmons and the Mafia blocked the way. The Mafia had control over Fitzsimmons and easy access to Teamster funds and did not want to deal with Hoffa. Hoffa, as Chuckie put it “He got nuts”. He made public threats and accusations against Fitzsimmons and the mobsters. So, it is hardly a surprise that in 1975 they took him out. That the Mafia was responsible is widely accepted, but exactly who ordered and carried out Hoffa’s abduction and murder is uncertain and subject to endless controversy. Goldsmith aims to clear his stepfather Chuckie who many believe picked up Hoffa to deliver him to his killers. He makes a strong case that Chuckie could not have been involved and there are federal prosecutors and criminologists who agree with him. Perhaps the best arguments are that the Mafia would not have trusted Chuckie with such a critical assignment and if he had been involved, they would have killed Chuckie afterwards. Goldsmith after becoming a Harvard law professor spent a lot of time interviewing Chuckie for the book and following up with FBI agents and prosecutors trying to get them to acknowledge that Chuckie is not a suspect in the case. We get some insight into the convoluted handling of the Hoffa case by the FBI and prosecutors.

I picked this book up because of interest in the mystery of Hoffa’s disappearance, but it had much more to offer. Recommended for readers who want some personal inside takes on the Hoffa case, the Teamsters and the Mafia relationship, lawless surveillance by the federal government particularly under RFK and later the Bush administration, and the wholesale corruption of the Nixon administration.
Profile Image for Brett C.
945 reviews227 followers
December 30, 2022
This was very intriguing. I appreciated the historical context of labor, biography of James Russle Hoffa, history of labor unions, the influence of the mafia, abuse of power, and the government's attempts ar getting answers.

Charles "Chuckie" O'Brien and his stepson (the author) Jack Goldsmith were not only involved but invested in the life of Jimmy Hoffa and that is characterized throughout the narrative. Chuckie was a prime suspect in the case as his adherence to the code of omertà has left enthusiasts in the dark. The narrative analyzed the collective resulting in the disappearance of Jimmy Hoffa, the begrudging committee investigations of the DOJ and Bobby Kennedy, and Teamsters.
Hoffa might have used his organizing acumen and control over transportation networks to lead the American labor movement in a very different direction than the one it in fact traveled. But his neglect of society's rules and etiquette—especially his many criminal associations—would destroy him, with tragic consequences for all the labor. pg 72
The author's tone was very even and neither emotional nor accusatory. With the evidence put out here we'll never know the truth about the disappearance of Jimmy Hoffa. This was a great book that tackled a lot of information but inna clear and coherent way. I would highly recommend this if you watched and enjoyed Hoffa (1992) and/or The Irishman (2019). Thanks!
Profile Image for Mark.
1,602 reviews133 followers
January 3, 2020
I have been a proud union member, for over 30 years and I was sixteen, when Hoffa disappeared, so I do remember that event, but I really never knew Hoffa's full story. With the film, The Irishman being recently released, along with this well-researched account, it gave me the perfect opportunity, to learn about this powerful union leader and what led up to his demise.
What also makes, this book special is that the author, a prominent lawyer and former government official, has a strong connection to this story. His step-father, Chuckie O' Brien, was Hoffa's right hand man for many years and was also arrested for his suspected involvement with Hoffa's disappearance, which destroyed Chuckie's life, despite his likely, innocence.
The author packs a lot into this book, and we get historical snapshots, of the FBI, Hoover, RFK, the teamsters, the mob and the sinister world of surveillance. Solid nonfiction.

**I also recommend seeing the Netflix film The Irishman, although the details, based on a book, by the alleged hitman, are highly questionable, it still is a terrific movie.
Profile Image for Ctgt.
1,797 reviews96 followers
November 11, 2019
Heard the author discussing the book on a podcast and thought it sounded intriguing. I knew the basics of the Hoffa story but I've never been a close follower, so much of this book was relatively new to me. Plenty of backstory on Hoffa, the Teamsters and the Mafia involvement. But the interesting part of this book was the relationship between the author and Chuckie O'Brien, Hoffa's close confidant. Just a fascinating look at the relationship between a stepfather/stepson and how it morphed over time. All in the shadow of Hoffa and his disappearance.

Recommended
8/10
Profile Image for Jill Meyer.
1,188 reviews121 followers
October 5, 2019
You know, there are some crimes that just aren’t going to be solved…at least publicly. One of those is the murder of Jimmy Hoffa, who disappeared one Wednesday afternoon in July, 1975. He was 62 years old and was the “retired” leader of the Teamsters Union. A few years before he had left Lewisburg Prison after serving a five year term for jury tampering, attempted bribery, and fraud. His early release from prison was supposedly facilitated by a bribe to Richard Nixon. There are a lot of bad actors in the Jimmy Hoffa story – both in the Teamsters and La Cosa Nostra and our own government. One of the suspects in the “disappearance” of Jimmy Hoffa was his “adopted” son, Charles “Chuckie” O’Brien. “Adoption” in this case is less a legal term than a term of endearment to a man who is helping in the raising of a boy and has welcomed that boy into his family.

“In Hoffa’s Shadow” is the story of Chuckie O’Brien and his devotion to his adopted father and his adherence to “Omerta”, or taking your secrets to your grave. The book’s author, Jack Goldsmith, is O’Brien’s step-son and is a professor at Harvard Law. Goldsmith’s mother married Chuckie O’Brien and O’Brien adopted her three sons. O’Brien and Goldsmith went through a 20 year or so period of estrangement but reunited thirty years ago.

Goldsmith’s book is as much about Chuckie O’Brien’s relationships with both his adopted father – Jimmy Hoffa – and his step-son, Jack Goldsmith, as it is about the kidnapping and presumed murder of Hoffa. It’s the story of a 40 plus year suspicion of O’Brien having picked up Hoffa that afternoon and taken him somewhere to be murdered and his body disposed of. And because the book covers two stories, it’s a bit disjointed, which is why I’m giving it four stars instead of five. It’s one of those books that should have been a bit better, but I can’t really tell you how it could have been better. Maybe a bit more judicious editing.

Chuckie O’Brien is an interesting man who has certainly led an interesting life. He was finally cleared – unofficially, of course – of his alleged part in the crime. He’s holding on to Omerta to the end, and we never do find out who he thinks killed Jimmy Hoffa.
123 reviews3 followers
December 21, 2019
There’s a lot to say here.

This is like 5 separate, good books. It’s an interesting autobiography. It’s an interesting biography of Chuckie O’Brien. It’s an interesting biography of Jimmy Hoffa. And is both an interesting history/mystery book and an interesting layman’s legal text.

I’d recommend it for any of those, separately. But together?

Yeah, read it.

And that’s before even considering the degree to which it’s really an exploration of family dynamics, the nature of loyalty and honor. Given the role that traditional, Sicilian values of honor, loyalty, and silence play in this story, it’s also particularly noteworthy that the work itself is silent on one of its central questions — no, not who killed Hoffa (okay, on that, too, largely); on what it is that justifies someone’s loyalty, when, what, and whom has the right to expect it, demand it, and receive it from others.

I don’t know that I’ll ever again have the chance to talk to Jack Goldsmith, but if I do, THAT is the main question I’d want to follow up with him on. Well, that and how his rethinking of his relationship with his step-father and the related realization that many of the positions he once took were taken in reaction to his step-father’s commitments have changed the positions themselves. But I probably won’t get to have those conversations.

Anyway, the book itself is a great springboard to them. And I’ll hope that the underlying convo gets to someday occur.
Profile Image for Tom.
445 reviews35 followers
April 3, 2020
Though Goldsmith doesn't say so explicitly, I couldn't help but think after finishing his book that it would not be a stretch to conclude that RFK, in his obsessive crusade against Hoffa, did more damage to the country's principles of rule of law than the Teamsters' leader ever did in funding mob real estate deals. Goldsmith, a former Justice Dept. lawyer in Bush II administration, argues that RFK set dangerous precedents regarding illegal searches and wiretaps that are still playing out today. Goldsmith's role in this alarming legacy is an intriguing part of the larger story, as he presents himself as a conscience-driven player doing his best to stifle the worst impulses of W. policies re data gathering and detention, while still supporting some highly questionable programs created in immediate aftermath of 9/11, all justified on grounds of national security. But this is not self-aggrandizing white-wash. Goldsmith readily acknowledges his own ambivalent feelings about many things, especially his on-again, off-again relationship with his step-father, Chuckie O'Brien, the hapless, proud, and, in his own way, principled henchman-gopher for Hoffa, whom he genuinely loved as a surrogate father. Some of the most poignant and dramatic sections describe Goldsmith's inner-struggles over how far to push O'Brien to violate his sacrosanct devotion to "omerta" -- the code of silence -- in revealing more about the players in Hoffa's disappearance. And he goes to great lengths to discover the truth about O'Brien's own involvement. These sections read like scenes in a legal thriller, at times. The climax to investigations by FBI and by Goldsmith are structured as effectively as in a novel. Goldsmith is an excellent writer, covering a lot of history, public and personal, all of which he deftly weaves together. Lots of labor history here, but all presented in service the larger personal drama. I'm tempted to give this one 5 stars, but at times the meticulous reporting of movements and motives of a large cast of figures, especially those surrounding the day of Hoffa's disappearance, can read somewhat like a police report. The audio narrator is quite good, capturing shifting tones adroitly. 4 1/2 stars.
Profile Image for Josh Craddock.
94 reviews6 followers
November 1, 2019
This was an unexpected thriller. I got the book because the author, Jack Goldsmith, was one of the professors I was closest with in law school. It turns out that his step-father is the lead suspect in the Hoffa disappearance. Goldsmith wrote the book because he studied the evidence, interviewed witnesses, and became convinced of his step-father’s innocence.

But this isn’t just a book about the Hoffa disappearance—it’s about the labor movement, organized crime, the surveillance state, fathers and sons, forgiveness and redemption. Part memoir, part history, part true crime, this book will appeal to a wide variety of audiences.
Profile Image for Cheryl.
98 reviews13 followers
October 12, 2023
My father met Jimmy Hoffa when he came to Tampa to organize the trucking company where he worked. He was a bit of a Hoffa junky ever since that time. Upon dad's death, I found this book in his personal collection so I decided to read it more as an attempt to remember my dad than a personal interest in Jimmy Hoffa.

Overall, I enjoyed the author's perspective as the adopted son of Hoffa's right-hand man and his attempt to uncover the truth of his dad's knowledge of what happened. I felt the book was thoroughly researched and honestly told. Through reading this book, I realized that I would actually like to learn more about another key character: Chuckie O'Brien's mother Sylvia Pagano who helped grease the ties between the mob and Hoffa's Teamsters.
Profile Image for Drtaxsacto.
691 reviews56 followers
November 5, 2019
In July 1975 Jimmy Hoffa, one of the most powerful labor leaders in our history disappeared. Jack Goldsmith is the adopted son of a key figure in the case, Charles "Chuckie" O'Brien who was Hoffa's gopher and almost an adopted son.

Goldsmith had two other fathers - his mother married a doctor after she divorced her first husband and then eventually married O'Brien. He had a complex relationship with O'Brien. For almost a decade and a half he renounced his step dad. Goldsmith studied law and eventually became a part of the Office of Legal Counsel in the Department of Justice. Indeed, he was one of the attorneys who opined on the legality of intense interrogation techniques that the US used after 9/11. He now teaches law at Harvard. But at some point he reconciled with his stepfather and then spent several years trying to understand the complex relationship he had with O'Brien and that O'Brien had with Hoffa.

This is a compelling story on many levels. O'Brien had close ties to mafia figures and Goldsmith got to know both Tony Jackalone and Tony Provenzano, they were almost like his uncles. O'Brien could not become a "made man" because he was Irish but he held to the code of omertà. O'Brien is credited by some authors as the guy who delivered Hoffa to his death. Goldsmith, after extensive research and many hours of conversation with his step-dad concludes that is simply not true. (The Irishman not withstanding).

There are some other parts of the story that I found interesting. O'Brien was hounded by the FBI even though at some point they concluded, based on an understanding of his timeline on the day of Hoffa's disappearance, that he could not have been involved. Near the end of his life Goldsmith tried to broker a deal with the FBI and the Federal Attorney which the Federal Attorney, seemingly for internal political reasons, reneged on. The over-reach of DOJ and FBI figures including RFK, Hoover and others is appalling.

Hoffa, I think, is portrayed realistically. He was intensely dedicated to his union but his commitment to transparency was non-existent. He skimmed tons of money from the Teamsters and at the same time built ties with the Mafia to help him establish a nationwide Teamsters contract.

I found the book interesting both from the personal reflections and because of the repeated excesses that government officials took to persecute O'Brien.
Profile Image for Abby.
226 reviews
July 22, 2020
Really good book about the details of Hoffa’s right hand man Chuckie O Brien. Trying to solve the mystery of Hoffa’s disappearance and recounting the details of the Teamsters and the Mob. Really enjoyed it. 4.5 stars!
Profile Image for Anand.
37 reviews
August 14, 2024
At its core, In Hoffa’s Shadow is a comprehensive and gripping history of the rise and fall of the Teamsters Union and Jimmy Hoffa. It also weaves in interesting narratives around government surveillance, the mafia, DOJ under Bobby Kennedy, and the unsolved mystery of Hoffa’s disappearance. But the most compelling part of the book is Goldsmith’s relationship with his stepfather, and his effort to clear his name.
Profile Image for Kevin.
121 reviews1 follower
July 3, 2021
I liked this a lot more than I thought I would.
Profile Image for Jim B.
879 reviews42 followers
August 6, 2023
I only vaguely remember Jimmy Hoffa, and my main memory is the event that is central to this book: Hoffa's disappearance. I wouldn't have read this book, but it was a gift to me from my historian son.

The author's stepfather loved and worked for Jimmy Hoffa. The author does an amazing job of capturing the complicated relationship between the author and his stepfather, and the devotion of his stepfather to their family and to Jimmy Hoffa and members of the Teamsters and the Mafia. In holding the tension of viewing criminal activity through the eyes of someone who was devoted in affection and respect to people we usually dismiss as "bad guys" Jack Goldsmith was able to show that people are far more complex than most historians are able to capture in their books.

An added bonus was learning about Bobby Kennedy and his impact in the way he conducted the work of U.S. Attorney General under his brother. In fact, although it's not mentioned in the title, the background of this book is the work of the Justice Department and the FBI. Again, the complexity of humans working in institutions was well described.
Profile Image for Al Kaelin.
14 reviews2 followers
September 12, 2023
Jack! Chuckie! You sonsabitches. Great read. I hate that Bobby Kennedy.

Might recommend to my dad. He loves mob movies.
Profile Image for Ella.
736 reviews154 followers
July 6, 2020
Basically a love-letter to a flawed father. I have a soft spot for Jack Goldsmith, and this book really surprised me. He seems like the most conservative, "rule of law", buttoned-down man possible. So to learn that Jack Goldsmith, who I know in a very different context, has this background and this life, nevermind was connected to the disappearance of Jimmy Hoffa -- well, it was mind-boggling and I had to read it!

Like every American of a certain age, Hoffa's disappearance holds an oversized spot in my imagination, and this may be the closest we'll come to getting an answer. But the bigger story is the love of a son for the man who raised him. This is the real reason I'm glad I read the book. YMMV.
Profile Image for sarah.
67 reviews1 follower
July 2, 2020
Such an interesting profile of a part of American history I knew fairly little about (mid 20th century FBI / the Mob / the Teamsters.) Exceeded expectations! Thanks for the rec Tamar
Profile Image for Amy.
5 reviews
July 23, 2024
Turns out I don’t care about Jimmy Hoffa
Profile Image for Kusaimamekirai.
714 reviews272 followers
December 16, 2019

In the case of many notorious or suspicious deaths, someone’s final days have a tendency in the memory to overshadow the totality of that person’s life. Few deaths can be said to be more notorious or suspicious than that of labor leader James Riddle Hoffa. While to put it mildly, Hoffa was no saint, he does deserve to have the totality of his life and accomplishments noted and not be reduced to his last hours outside the Red Fox restaurant in suburban Michigan. Hoffa was a tireless advocate for blue collar workers, and he labored nonstop while doing anything and everything (both legal and otherwise) to give them a better standard of living. Hoffa like most outsized personalities flew a little too close to mafia and government shaped suns which would eventually consume him.
And yet, this book isn’t really about Jimmy Hoffa. Yes, it does detail some of his accomplishments and ethically questionable practices, but this book is more about the author’s stepfather Charles “Chuckie” O’Brien and his relationship with him. As Hoffa’s right hand man of 30+ years, O’Brien was anywhere and everywhere Hoffa was, making him a link to history that few people ever are. O’Brien was also, after a falling out with Hoffa, the main suspect in the abetting of Hoffa’s eventual disappearance in 1975.
This book then is more a culmination of interviews the author had with O’Brien about Hoffa’s disappearance but also often delves into delicate questions of memory. Which memories after all should be resurrected and which memories should stay buried? O’Brien as someone with extensive mafia ties is hesitant to ever really say what he knows about that day however (outside of proclaiming his own innocence) to the occasional frustration of his stepson.
Suffice it to say though that “Chuckie” is about as fascinating and as tragic a character you’re likely to come across. Thirty years as Hoffa’s servant essentially, and never allowed to advance in the union hierarchy as he wished. Deeply loyal and attached to Hoffa, he was crushed at his disappearance but also cognizant of the competing forces from the government demanding information from him and the mafia demanding he withhold it. “Chuckie” comes across as basically a decent guy, if not a serial dissembler of the truth, who never really caught a break in his entire life.
Likewise caught up in his own ethical quandaries is the author, a former national security lawyer in the George W. Bush administration charged with overseeing the legality of the Patriot Act and someone who tells us that his moral compass wouldn’t allow him to clear the entirety of the Patriot Act (he could however find legal justifications for portions of it).
The author reminds us as well that having a notorious stepfather who was the prime suspect in Jimmy Hoffa’s disappearance, as well as mob connections, was not an easy thing to come to terms with as he began his ascent up the government career ladder.
In a strange way however, this book’s attempt to answer questions about “Chuckie’s” guilt, and the author’s realization that the government is not always on your side, brings him closer to his stepfather who had shunned for many years. They discover that they have much more in common than they had ever realized via their mistreatment and distrust of the federal government.
While in my eyes the author fails to establish that “Chuckie” wasn’t involved in some way with Hoffa’s disappearance (despite his claim to have fully exonerated him, he is just too close to the case to maintain credibility for me) but he ends up writing a much more interesting book in the process about family and loyalty (no matter how seemingly misplaced). Chuckie’s story reminds us that at the end of the day when everyone and everything turns against you, these are the only things we have left to turn to.
Profile Image for Larry Bassett.
1,628 reviews338 followers
September 16, 2021
Just in case you think this book is going to tell you exactly what actually happened to Jimmy Hoffa on July 30, 1975, let me quote you the last few lines of the book.

“I’m not being critical,” I continued. “And I know why keeping your mouth shut is so important. But I don’t understand why you’re the only person who has to take it to your grave. There are so many things that would be served by you telling the truth. I just cannot believe that you hold the secret to the greatest mystery in American history in your head and you’re not going to tell the world. I can’t believe it.” “Believe it, Jack,” Chuckie said.

The author of this book is the stepson of a man who was very close to Jimmy Hoffa for a very long time and was also close to many of Hoffa’s notorious friends. And enemies. He is also an attorney who had risen to considerable heights in the government and gained access to many documents and a good deal of information that has led to a seemingly thorough examination Of the life and death of Jimmy Hoffa. The book is written with both a good deal of directness as well as a good deal of diplomacy and respect for the family of which he is a part.
Profile Image for Laura Henderson.
45 reviews
August 3, 2021
I was living in Lansing, MI, working two waitressing jobs and preparing for graduate school at Michigan State when Jimmy Hoffa vanished. I didn't follow the story closely and didn't know (or don't remember) that Chuckie O'Brien was the prime suspect.

This well-written, well-researched book filled in a lot of details about Jimmy Hoffa and his disappearance. It also explained to me why Bobby Kennedy was disliked so intensely. I was a child when he was Attorney General and really only aware of him when he ran for President. The man who was Attorney General and the man who ran for President might as well have been two different people.

The book dragged for me in the sections that describe in great detail how LCN (La Cosa Nostra) worked and who was connected to whom. Then Nixon enters the story and the book takes off again.

Jack Goldsmith's love for Chuckie O'Brien shines through. The best sections are those that describe Chuckie and Jack's relationship. Jack doesn't hide the warts and faces up to his own flaws, but his regard for Chuckie never flags.
Profile Image for Becky.
334 reviews21 followers
March 14, 2020
I read this book in preparation for my annual murder mystery birthday party, and I enjoyed it. But it felt too much like it was written to exonerate the author's stepfather, not to help us find out what actually happened. I guess that's because his stepfather was such an integral source and had a certain amount of control over the narrative, though I did find he did his journalistic due diligence. But there were some pages where it was so much of what Chuckie said and I wanted to hear from more sources, I wanted to find out what actually happened. Anyway, I think this book was probably still my best bet at getting at what happened, beyond getting FBI records from Detroit. I did find I struggled to want to keep reading it sometimes though.
Profile Image for Richard.
723 reviews31 followers
February 26, 2020
After Seeing The Irishman, I picked this up at the library.
I didn't expect much. This is one of the best books I've read about government over reach, the mob, the fbi etc. Jack is Chuckie O'Bien's step son and worked with John Ashcroft and worked through the legality of the government surveillance programs and torture policies post 9-11.
He really lays into RFK who has always sidestepped his part in the FBI's criminal harassment of MLK, but obviously ok'd it.
Profile Image for Colette.
230 reviews
January 12, 2020
When I purchased this book it sounded like an interesting story, but I had no idea who Jimmy Hoffa or Chuckie O’Brien were. A few weeks after my purchase, I watched Martin Scorsese’s, The Irishman- which discusses Jimmy Hoffa’s relationship with the mob and his disappearance.

Thankfully, the book tells a very different version of events that lead to Jimmy Hoffa’s still unsolved disappearance. Chuckie O’Brien relationship with Hoffa was very father/son like, even though they were not related. Chuckie was Hoffa’s right hand man through Hoffa’s presidency with the Teamsters union, his feud with Robert F Kennedy, FBI corruption, his jail time, and of course his connections with the mafia. The question remains, did O’Brien have involvement in his disappearance? Author and stepson to O’Brien does a wonderful job disproving this, while keeping the reader captivated with facts and proof.

If you like American history, cold cases, or mob stories then this should be on your list to read in 2020. Plus you won’t have to deal with Scorsese trying to convince you Robert DeNiro could play an Irish man.
2 reviews1 follower
July 30, 2020
This was a engrossing book. The author, the stepson of a close associate of Jimmy Hoffa, weaves his personal history into a fascinating account that includes the history of the labor movement, the mafia, and the excesses of the Department of Justice.
Profile Image for Terry Feix.
96 reviews17 followers
October 8, 2019
The author is a Yale law grad, was head of the Office of Legal Counsel to the President, served in the DOJ and teaches at Harvard Law. Oh, and he’s also Chuckie O’Brien’s adopted son! Chuckie was Hoffa’s right hand man and chief suspect in his death. Great read.
Profile Image for UChicagoLaw.
620 reviews209 followers
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December 5, 2019
A remarkable book by former colleague and former head of the Office of Legal Counsel that is at once heart-felt memoir, murder mystery, and account of the infiltration of organized crime into organized labor. —Douglas G. Baird, Harry A. Bigelow Distinguished Service Professor of Law
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