© 2024 WFAE

Mailing Address:
8801 J.M. Keynes Dr. Ste. 91
Charlotte NC 28262
Tax ID: 56-1803808
90.7 Charlotte 93.7 Southern Pines 90.3 Hickory 106.1 Laurinburg
Play Live Radio
Next Up:
0:00 0:00
Available On Air Stations

'In Hoffa's Shadow' Uncovers An Author's Family Ties To A Mafia Mystery


This is FRESH AIR. I'm Terry Gross. The new Martin Scorsese film "The Irishman" will introduce a new generation of Americans to Jimmy Hoffa, the tough, mob-connected leader of the Teamsters Union who vanished and was presumed murdered in 1975. Hoffa's disappearance is one of the greatest unsolved crimes of the 20th century.

Our guest, Jack Goldsmith, has a close family connection to Jimmy Hoffa and to his mysterious demise. Goldsmith is a Harvard law professor, but he's best known for having headed the Office of Legal Counsel in the George W. Bush administration. During his tenure, he challenged the warrantless wiretapping program and withdrew two memos written before his tenure justifying the use of torture in the war against terrorism.

Goldsmith's new memoir, "In Hoffa's Shadow," is about his investigation into his stepfather's role in Hoffa's disappearance. Goldsmith's stepfather, Chuck O'Brien, was a close associate of Hoffa's for decades. And when Hoffa disappeared, O'Brien was suspected of having driven him to his execution. O'Brien is portrayed in Scorsese's new film by Jesse Plemons. Al Pacino plays Hoffa. Jack Goldsmith spoke with FRESH AIR's Dave Davies.


Well, Jack Goldsmith, welcome to FRESH AIR. This is quite a story. And there's a couple of generations of Americans who don't remember Jimmy Hoffa. So why don't you just tell us a little bit about who he was and his place in the American labor movement?

JACK GOLDSMITH: Sure. Thank you for having me on. Jimmy Hoffa was the president of the Teamsters Union from 1957 to 1967. The Teamsters Union was at the time the largest union in the country and the most powerful. Hoffa rose to become the head of the Teamsters Union from Detroit, where he expanded his power over the decades. He was simultaneously the best-known labor leader in the country, the most powerful labor leader in the country, and also probably the most corrupt. He had ties to organized crime. He was defiant of the law. But he was much beloved by the members of his union because he was very successful in raising their standards of living.

DAVIES: Right. And, of course, he was driven from the presidency of the Teamsters after some criminal convictions. The Justice Department went after him in a very big way. And then, in 1975, he disappeared and is presumed to have been murdered. That's one of the great unsolved cases of the 20th century. You were, I guess, in about eighth grade or so, then, right? And...

GOLDSMITH: I was 12 years old. I think I was in...


GOLDSMITH: What was I in? Sixth grade.

DAVIES: OK. And your family's life intersected with this case in a very personal way. Explain that for us.

GOLDSMITH: Six weeks before Hoffa disappeared, which was on July 30, 1975, my mother married a man named Charles - Chuckie - O'Brien. And it turned out that Chuckie O'Brien, who was my stepfather at that point, was Jimmy Hoffa's longtime right-hand man and most intimate aide. And then, after the disappearance six weeks after my mom married him, he soon became the leading suspect in the disappearance. And it was believed that he picked up Hoffa at a - outside of a restaurant where he was waiting and delivered him to his killers.

DAVIES: How did this affect you and your family life?

GOLDSMITH: Well, it had an - just an extraordinary impact. And it's hard to exaggerate how - what a national circus the Hoffa disappearance was. It was front-page news and on the evening news every night for weeks. It was the largest - one of the two largest investigations the FBI ever had. Chuckie was the central suspect and on the front pages every day.

And so our lives were completely overwhelmed by it. My mother at the time had been suffering from severe mental health issues, and they got a lot worse because of this, understandably. And so it basically was a life-wrecker. I mean, he was accused on the front page of every newspaper then and ever since of basically picking up his - a man that was like a father to him and taking him to his death.

DAVIES: Wow. And you were a kid. What did it feel like?

GOLDSMITH: Was 12 years old when the disappearance happened. It was a discombobulating time, to put it mildly. I had a new stepfather, and I loved my new stepfather. He had immediately, from the time I met him - I had met him about six months earlier - and we had become intensely close. He was - had a huge influence on my life. He was incredibly loving and supportive and gave me attention that I'd never received. My real father left when I was very young. And so I was deeply loyal to him, and then this happened.

And he portrayed it as a setup at the time. And I basically believed him at the time and believed everything else he told me at the time about the mob, the government setup and the like. And - but having said that, it was it was still very, very difficult because, you know, we were bombarded with newspaper reporters and accusations. My mom's mental - my mom's health was spinning out of control. And my new stepfather seemed to be in terrible trouble.

DAVIES: What was Chuckie like? Tell us about him.

GOLDSMITH: So he was an amazing guy. I mean, he wasn't - he was not a man who was well-educated. And he was not someone who - I see now from my current perspective - who cared much about the law. But he had a very firm sense of right and wrong, and he taught us right from wrong in a way that had a huge impact on my life. The main thing I can say about him was that, despite all of his troubles, he spent all of his time, every second of his free time devoted to me and my two brothers and just everything we did.

And it's hard to exaggerate what an impact this had on me because, as I say, I was basically fatherless for the first 12 years. And it was the first time any male attention had ever come my way to that degree. And so he basically did everything we wanted to do. We went to distant comic book stores to get comic books. He always seemed to be able to get us tickets to sports events even though he always had money troubles. He went to all of our athletic events. He had big cookouts for my team. And he was just a hugely supportive, loving father.

DAVIES: Right. And there were a couple of mob figures that he was close to who you got to know, right?

GOLDSMITH: Sure. One was Anthony Giacalone, a senior organized crime official in Detroit, and another one was Anthony Provenzano, a Teamsters official and a member of the Genovese family in New Jersey. And, of course, when I was a teenager, I didn't know any of this. I mean, I read the newspapers and saw them referred to as mobsters. But to me, they were Uncle Tony and Uncle Tony. And they were, you know, upstanding gentlemen.

Uncle Tony Giacalone was impeccably dressed. He had a beautiful apartment that we used to go to a lot. Uncle Tony Provenzano had an amazing pool table, and we used to play there a lot. And he ended up giving us that pool table one day. So I was very close to these people who were being described in the newspapers as these horrible, violent mobsters. But to me, they were family.

DAVIES: We're speaking with Jack Goldsmith. His new book is called "In Hoffa's Shadow." We'll talk more after a short break. This is FRESH AIR.


DAVIES: This is FRESH AIR, and we're speaking with Jack Goldsmith. He headed the Office of Legal Counsel in the George W. Bush administration for a time, where he was involved in critical battles over the legality of interrogation techniques and warrantless surveillance of American citizens. His new memoir focuses on a very different story, his stepfather Chuck O'Brien's close connection to labor leader Jimmy Hoffa and the suspicion many held for years that O'Brien was connected to Hoffa's 1975 disappearance. Jack Goldsmith's book is called "In Hoffa's Shadow."

Part of this book is sort of a look at the American labor movement and Jimmy Hoffa's life. And it's fascinating. You know, he had a reputation as a guy who was, you know, violent and corrupt and kind of the worst of the American labor movement. And you argue there's really more to his story. Tell us what people don't know about Hoffa - his life and motivations.

GOLDSMITH: There's much more to the story. And I really do think that only one half of Hoffa's career has been told, the one you just described. He came up through organized labor the hard way in the 1930s, which was the most violent time in American labor history. He was in - constantly fighting with police and management in truly violent street fights where employers, with the state behind it, was truly violent towards efforts to organize labor unions, at a time when the American worker was in just a terrible, terrible shape. So this is the world he grew up in as a young man, and it colored the way he looked at labor relations with management and the government for the rest of his life.

I mean, he basically assumed from that early period, when he saw the state and management together fighting unions in violent ways, he basically assumed and believed that was the way of the world ever since. And that shaped his outlook. He was also - it's not well-known, but he was also a true genius - and this is not a word that - this is not just something I think. It's what labor historians who have studied his career have said - a true genius at bargaining and organizing.

And he built out the Teamsters union, and he leveraged the power over transportation and the ability to shut down transportation, which was at the heart of the economy, to expand his power nationwide to the point where, right at the height of his career, right when he was at the height of his criminal trouble, he won an historic nationwide labor pact that was really the highlight of his 20 years of dramatically expanding wages and benefits for the hundreds of thousands of people in the union. That was actually over a million at that point.

So he was a very important person in the labor movement, and very consequential and very good at what he did, despite the fact that, as you say, he was a serial lawbreaker and had all sorts of corrupt ties.

DAVIES: You know, and it's pretty remarkable to have gotten a national contract for truck drivers when you consider the fact that, you know, truck - the trucking industry was pretty decentralized. You're talking about hundreds of different employers, and all over the country. And what's interesting, as you tell the story, is that one of the ways he got so connected to the mob was in trying to get all of these different locals unified and negotiating together for a national contract. And he was from Detroit, but a lot of the locals in the East had some serious mob ties. How did that affect his relationship with organized crime?

GOLDSMITH: Well, his relationship with organized crime began earlier in Detroit in the 1940s. But the relationship between unions in Detroit and the mob there was one of arm's length, and the mob didn't control unions in Detroit. But when Hoffa tried to expand his power nationally, he met and encountered lots of unions that were mob controlled, especially in the East in New York and New Jersey. And basically - and he also had to - it was important to get a national contract to slow down wages in the large cities so he could bring up wages elsewhere so that basically it meant that the unions in the big cities would have to, at least in the short term, take a hit.

So to make a long story short, he basically had to accommodate the mob that controlled these unions in order to both win the presidency of the union and achieve his goal of winning a national contract. And for Hoffa, I don't think he blinked. I don't think he gave it a second thought. His basic view was that he would do business with anyone on any terms which he found advantageous to him and his union. And so I think that his deal with the mob in the East to win their support for going slow on wages and giving him support for the presidency, for Hoffa, that was just like bargaining with employers or bargaining or, you know, giving money to politicians or judges that he thought would bring him an advantage.

DAVIES: It's interesting, you say he was not particularly attracted to mob life, mob culture, right?

GOLDSMITH: Yeah. This is something that Chuckie taught me that I certainly didn't appreciate from my research. Hoffa's always referred to as mobbed up and mob connected, and that's certainly true. He had relations with the mafia all over the country. But they were always at arm's length and, as Chuckie said to me, he never really understood the Italians. (Laughter). He didn't understand their rituals. He didn't understand the code of silence. He didn't understand how they kissed each other when they saw each other, and he didn't understand their organization.

He basically dealt with the person in charge of the place or in the context where he needed help. And that was often with the mob. And he just basically viewed it as a transaction like his other transactions. Now, the most significant transactions he had were with loaning money to the mob for various projects that they had. And that brought Hoffa huge, huge amounts of money, personally and for the Teamsters union. And but for him, as I say, it wasn't like he was hanging out, going to dinner with these guys or spending a lot of time with them. He was - for him, it was just part of doing business.

DAVIES: Didn't drink, right? Worked around the clock.

GOLDSMITH: He was a workaholic. He didn't drink. He was very, very moralistic. He didn't like it when guys screwed around, as he would say, when some of his people that worked for him were having affairs. He was strangely moralistic given that he was such a serial lawbreaker. He spent almost all of his waking hours with the locals, hanging out with members of the union, listening to them. He gave away his telephone number, and he would literally field collect phone calls day and night from any member of the union. He was extraordinarily committed to his union, and that's where he spent all of his time, even when he was on trial. And he had many, many trials. He would go to trial in the morning and then in the afternoon, in the hotel where they had a suite, they would - he would basically set up an office on the road and spend the afternoon and evening doing union business.

DAVIES: As Hoffa was having these battles and building his union career, your stepdad Chuckie was with him. You didn't know him yet. That came later. But as you came to understand it, what was Chuckie's relationship with Hoffa and his role in the union?

GOLDSMITH: Chuckie met Hoffa when he was 9 years old. He was introduced to him by his mother, Sylvia Pagano. And Sylvia Pagano was actually a very important person in this story because she introduced Hoffa to the mob in Detroit and to other mobsters around the country. And she was a very consequential figure in Hoffa's relationships with organized crime.

So Chuckie knew Hoffa and was close to him since he was 9 years old. And then, when he was 18, he wanted to get a job in the union, and Hoffa eventually gave him a very low-level job as an organizer, as a business agent. But then when Hoffa became president of the union in 1957, when Chuckie was just, I think, 23 years old, he asked Chuckie to basically be a special assistant. And from that point on, from 1957 until Hoffa went to prison in 1971, Chuckie was basically always at Hoffa's side.

He was basically - I mean, a factotum seems like it's not a very attractive word, but that's basically what he was. He took care of anything and everything Hoffa needed, from meals to organizing meetings to collecting intelligence; he was also a bodyguard. He would tie his tie in the morning because Hoffa never was very good at tying a tie. He was basically his around-the-clock assistant.

But they - it was more than just that. They were extremely close. And everyone believed - because they were so close and because Hoffa was always covering for Chuckie or showing affection to Chuckie that he usually didn't show to others, everyone assumed - and it was widely rumored - that Hoffa was actually his real father.

DAVIES: You don't think that's the case.

GOLDSMITH: I spent a lot of time digging, and I do not believe that's the case. I think the reason people believe that is because Hoffa was very, very close to Chuckie's mother, Sylvia, and because he had showed such affection to Chuckie. But no, I don't believe it's the case. I mean, if for no other reason than that at the time Jackie was born, in the year two before, there's no reason to think that Chuckie's mother and Hoffa were in the same town or near one another. But also, Chuckie insists that it wasn't true, and I believe him.

DAVIES: He would do almost anything for Jimmy Hoffa. What are a couple of the wilder moments in his service of Jimmy Hoffa?

GOLDSMITH: He said to me many times that he would do anything for Jimmy Hoffa. Some of the stories I recount in the book are - one of the funniest ones - I guess it's funny - is the time when Hoffa was complaining about the editor of The Detroit News, who was incessantly pounding Hoffa and his corruption and the like in a way that Hoffa thought was unfair. And he told Chuckie to take care of it and do whatever he needed to get the guy to turn it down.

So Chuckie got the brilliant idea of going to the Wayne County morgue, where he purchased a cadaver - or purchased, I should say, the head of a cadaver, put it in a box, wrapped up the box and put a note in it - he didn't tell me what the note said - and sent it to Martin Hayden, who was the editor of The Detroit News. That's one thing he...

DAVIES: Do we know what his reaction was?

GOLDSMITH: We don't know what his reaction was. I mean, I actually was able to confirm the story through a variety of sources. But I wasn't - Hayden is no longer with us, and I wasn't able to figure out what his reaction was.

DAVIES: So Hoffa's big enemy for a long, long time was Bobby Kennedy, who first went after Hoffa and the Teamsters as an investigator for a Senate committee. And there was clearly deep personal animosity between these two men. He then - after his brother Jack Kennedy was elected president, Bobby Kennedy became the attorney general, and he kept going after Hoffa, seeking criminal convictions. And some were eventually secured. Kennedy was, as attorney general, very aggressive with surveillance of Hoffa and others. Was it legal surveillance?

GOLDSMITH: So there was a lot of illegal surveillance going on during Bobby Kennedy's tenure as attorney general, and large swaths of it were clearly illegal. The bugging that was going on against organized crime at the time was - flew in the face of clear Supreme Court directives that it wasn't allowed. You weren't allowed to bug a private abode through a break-in, which is what the FBI was doing.

Kennedy was also - and his department were also super aggressive in surveilling Hoffa personally, sometimes through wiretaps and bugs. Hoffa was never able to prove that Kennedy acted illegally against him. And there's some evidence in the book that I was able to collect that shows that maybe there was some illegal surveillance against Hoffa. But more generally, in addition to the illegal surveillance that was all around Hoffa and through which the Department of Justice and the FBI were learning a lot about Hoffa, including about his trials, Kennedy just pushed the envelope in terms of prosecutorial discretion and throwing all of his resources against Hoffa and being super aggressive and using every trick in the book. In the way that he talked about the case in public - his brother, at the first debate in - against Nixon, pledged that if he became president, he and his brother were going to put Hoffa in jail. So there were a lot of ways that he crossed the line, surveillance being one of them.

GROSS: We're listening to the interview FRESH AIR's Dave Davies recorded with Jack Goldsmith, author of the new book "In Hoffa's Shadow: A Stepfather, A Disappearance In Detroit, And My Search For The Truth." After a break, Goldsmith will talk about his efforts to get to the bottom of his stepfather's involvement in the Hoffa case and what happened when he talked to the FBI agents who'd worked on the investigation. I'm Terry Gross. This is FRESH AIR.


GROSS: This is FRESH AIR. I'm Terry Gross. Let's get back to the interview FRESH AIR's Dave Davies recorded with Jack Goldsmith. He's a Harvard law professor and was a top government lawyer in the George W. Bush administration. But his new book, "In Hoffa's Shadow," is about his stepfather, Chuck O'Brien, who was a close associate of the tough, mob-connected labor leader Jimmy Hoffa, who disappeared and was presumed murdered in 1975.

O'Brien is a character in the new Martin Scorsese film "The Irishman." He's played by Jesse Plemons. Jimmy Hoffa is portrayed by Al Pacino. Chuck O'Brien came into Goldsmith's life just weeks before Hoffa vanished when O'Brien married Goldsmith's mother. He would soon be named by the FBI as a suspect in Hoffa's disappearance.

DAVIES: So all of this remarkable stuff about Hoffa's career, his battles with Kennedy, his self-enrichment, his ties with the law, his eventual conviction and imprisonment happens before you get to know your stepfather Chuckie. He comes into your life right around the time that Hoffa disappears in 1975. And, you know, you find him a loving and devoted father for many years after that. In fact, you change your name from Jack Goldsmith to Jack O'Brien, taking your stepdad's name. But then your attitude towards him changes. Tell us why. What happened?

GOLDSMITH: So what happened was I went to college. And when I went to college, I - a lot of things started changing. First, I started to think about my future and my life in a way that I really hadn't before I got to college. I wasn't a terribly serious high school student. And I hadn't really focused on my life beyond high school when I was in high school.

In college, I began for the first time to read some of the new books about the Hoffa disappearance. And these new books painted Chuckie and Uncle Tony Giacalone and Uncle Tony Provenzano in objectively unflattering lights. And so the kind of myth that Chuckie had perpetuated when I was a teenager and that I bought completely, by the time I got to college, I started to see that there was a quite different reality behind that. Also in college, I started to become embarrassed by Chuckie.

I used to revel in his labor identity and the union identity. I used to revel in, or at least enjoy, his rough language and his indifference to education. His nickname for me was - even in high school, but especially in college - the educated idiot, which was kind of indicative of how he thought about education. He didn't think much of education. He got his education in the streets, and he thought book learning was worthless. I used to - I became to have a different attitude about that.

One afternoon in my sophomore year, my car was repossessed by a very thuggish-looking repo man in a way - this was the car that Chuckie had given me, and he had not been able to make the payments on it - and the car was taken away from me in a very embarrassing and threatening way, and that kind of scared me. And I started to think maybe my association with Chuckie will have a bad impact or a dangerous impact on my life.

And then, finally, I started thinking in college, but especially in law school, about my career. And I decided in college that I wanted to be a lawyer. And I started to think that maybe it wouldn't be such a great thing to be a lawyer - and especially if I wanted to work in the government, which I had a dim ambition to do at the time, it wouldn't be so great to be associated with the leading suspect in the Hoffa disappearance and his organized crime friends.

DAVIES: Right. So you actually get your name changed back to Jack Goldsmith, and you write your stepdad a letter. What did you tell him? How did he respond?

GOLDSMITH: The week after graduation - he came to my graduation. And I - as I recall, I was a bit distant at my graduation towards him. A week after graduation, I was in Memphis, Tenn., where I was born. I was working there for the summer. And I decided the week after graduation, something I'd been thinking about for the last year or so, that I was going to change my name, at - which at the time was O'Brien since he had adopted me - back to Goldsmith, which was my - the name with which I was born. Since I was born in Memphis and had done the name change there, it was easy for me to do there.

So on Father's Day in 1980, I wrote him a letter, kind of a strangely upbeat letter wishing him Father's - happy Father's Day, telling him how much I loved him and telling him that the name change, which I had told him about in a phone call the week earlier, was no big deal - I still loved him - but that I just wanted to have my own name. And I tried to be upbeat about it. It was a pretty unconvincing letter, to read it today.

He responded by sending me an extraordinary eight or nine-page letter written on the stationery of the International Brotherhood of Teamsters, handwritten in his kind of looping cursive handwriting. And it was something that he later told me he spent a week on all around the clock. He talked to a lot of people about it. He practiced his handwriting so that he wouldn't make spelling mistakes. And it was just an extraordinary letter about how much he loved me and how hurt he was by what I did and how much it had hurt my family, my little brothers who - still O'Brien, my mother.

But it was also a letter that said, you have to decide for yourself, son. You're an adult, and you have to make decisions for yourself. And I can accept this. It's going to hurt me a lot, but I accept it. And I love you very much. That's a short summary of what was really an extraordinary letter, but that's basically what it said.

DAVIES: And then you really barely had any contact with him for, like, close to 20 years, right?

GOLDSMITH: So that was in 1980. By the time I got to law school in '86, I had basically decided that I wasn't going to talk to him anymore. And I basically cut him out of my life, and I was kind of brutal about it. And we didn't speak again. We barely spoke again, and I didn't see him for a couple of decades.

DAVIES: You graduated from - was it Yale Law School?


DAVIES: And you ended up having a very eventful turn as the head of the Justice Department's Office of Legal Counsel in the George W. Bush administration when you encountered the enhanced interrogation techniques that were being used in the wake of 9/11, as well as the surveillance of American citizens, and wrote legal memoranda undermining the justifications for that, which led to some serious confrontations in the government. You wrote a whole book about this. It's been written about a fair amount. You left after, I guess, nine months. But I bring it up because I wonder if your looking at, you know, the unconstrained power of government had something to do with reconsidering your relationship with Chuck.

GOLDSMITH: It did, in a kind of surprising moment and then a reflection upon that moment during my time in government. When I was working on trying to understand the warrantless wiretapping program that had been in place since 2001 - this was in the fall of 2003, or the late fall of 2003 - and in the middle of working on that case on - about warrantless wiretapping, I came across an important Supreme Court opinion that had a citation in it to O'Brien vs. United States. And I thought, that's strange. It was in the mid-1960's. I knew that was the time when Chuckie was having some troubles with the government in connection with Hoffa. So I looked up the case, and it was actually a case about my stepfather Chuckie. And it was actually a case where the government had illegally surveilled in a way that overheard conversations with his lawyer, and the Supreme Court had basically invalidated the conviction and ordered a retrial.

So this was an extraordinary moment for me for a lot of reasons. When I was a teenager, Chuckie had always kind of gone on in his not really legally informed but insistent way that the government always cut corners. He called it backup. The government always was able to break the law in secret when they were going after people in public for breaking the law. And he'd always said that he had a famous Supreme Court case and that the government had surveilled him illegally, and I really didn't believe any of it.

And I didn't know about this case in law school, and I didn't believe any of that stuff that he had said. And here I was in the Justice Department, working on a program that was - could be described as legal corner-cutting, to put it nicely, involving a surveillance program and seeing smart lawyers who had worked on his case who had made what I viewed as opportunistic interpretations to help support an intelligence program of the president to meet the enemy within, so to speak.

And in some sense, exactly what Chuckie had said to me when I was a teenager turned out to be true when I was in the Justice Department, so - in a different context, of course. So that was a moment - I certainly didn't flip on a dime right there and say, OK, I forgive Chuckie and I was wrong about everything, but that was the moment in which I started to rethink him and me and my - what I'd done to him. And maybe - and I started to rethink that maybe I wasn't so smart and I wasn't so justified in my moral superiority to him when I was a younger man and in my really poor treatment of him during my young adulthood.

DAVIES: Wow. So you left the Justice Department in, like, mid-2004, and this would've been nearly 30 years after Jimmy Hoffa's disappearance, nearly 30 years after Chuckie was identified publicly as the guy who probably drove Hoffa to his death. How widely known and widely shared and celebrated was his alleged role in this? I mean, there were even Hollywood films with him as a character, right?

GOLDSMITH: It was - it's not just - it's assumed truth everywhere you look. There are a dozen books who have placed Chuckie in the car picking up Hoffa. There are a couple of movies. There was the Jack Nicholson movie "Hoffa." I think that was in the '80s. There are thousands upon thousands of stories that have placed Chuckie in the car.

The reason that the public believes, and has believed since 1975, that he was the person who actually picked up Hoffa and drove him to his death because that was the early FBI theory. It was mentioned in an early FBI report that was leaked to the press, and that early report from 1976 has basically been assumed truth about the case ever since then. And it certainly was in 2004, and frankly, it is today. If you - you know, if you google O'Brien and Hoffa, you will find thousands of stories saying he drove Hoffa to his death.

DAVIES: Right, and there's a new Martin Scorsese film coming out, "The Irishman," and Chuckie's a character - right? - played by Jesse Plemons.

GOLDSMITH: Chuckie is a character played by Jesse Plemons. I haven't seen the film yet, obviously, but the book upon which it is based - like every book that's been written about this, basically, and every story - has Chuckie in the car picking up Hoffa.

DAVIES: We're speaking with Jack Goldsmith. His new memoir is "In Hoffa's Shadow: A Stepfather, A Disappearance In Detroit, And My Search For The Truth." We'll talk more after a short break. This is FRESH AIR.


DAVIES: This is FRESH AIR, and we're speaking with Jack Goldsmith. He headed the Office of Legal Counsel in the George W. Bush administration for a time, where he was involved in critical battles over the legality of interrogation techniques and warrantless surveillance of American citizens. His new memoir focuses on a very different story, his stepfather Chuck O'Brien's close connection to labor leader Jimmy Hoffa and the suspicion many held for years that O'Brien was connected to Hoffa's 1975 disappearance. Jack Goldsmith's book is called "In Hoffa's Shadow."

You eventually decide you're going to try and get to the bottom of at least Chuckie's role. Well, first of all, how did you reconcile with him? What was that like?

GOLDSMITH: So it happened at Christmas of 2004 about six months after I left the government, and my wife and my two very young sons and I went down there to see my mother for Christmas. For the last 20 years, I refused to visit my mom with one exception - when Chuckie was there - because I just didn't want to even be seen with him. But I decided this time, for a bunch of reasons, that it would be fine if he were there. He was actually quite sick. He had had heart surgery. He had diabetes. And my mom basically said, I can't ask him to leave. If you want to come down here, he's going to be here.

In any event, I had been thinking in the months before that I had terribly wronged him earlier when I had renounced him and basically cut him out of my life, and I had come to realize what extraordinary pain I had caused him, in large part because of my own children. I didn't really appreciate at the time when I was 21, when I sent him - when I basically changed my name and renounced him. I just had no conception of how painful that could be, even though my mom had told me how bad it was.

And it was really having my own children. It was also reflecting on how sort of moralistic and righteous I was in thinking he was a bad person and I was a good person. I came to think that it was much more complicated than that, especially after, you know, I had been knee-deep in some problematic activities in the government.

A whole bunch of things led me to change my mind and want to apologize to him and - but it happened one night very simply. We were - when I got down there, I was nice to him for the first time in 25 years. He responded as if nothing had ever happened. We had a great couple of days together. We cooked together. We shopped together. He took care of my baby children. And then one night when we were watching "Seinfeld," in a commercial, I just turned to him and I said to him, I'm so very sorry for what I did for you for the last 20 years. I was wrong, and I hope you'll forgive me and let me come back into your life. And he looked at me with this puzzled expression, and he started crying. And he basically said, you don't need to apologize, son. I understand why you did what you did.

And that was basically it, and we - that was it. We - from that moment on, we - he never brought it up again. We talked about it sometimes a decade later, but never in any way that caused him to bring up those 20 years in a bad way. And after that, we grew very, very close through conversation and travel together and the like.

DAVIES: Still painful to think about that?

GOLDSMITH: It's - every time I think about what I did to him and what - the pain he went through, it's very, very painful, yes.

DAVIES: You decide you're going to try and get to the bottom of Chuckie's - at least Chuckie's role in the Hoffa case. And, you know, you're a lawyer. You're a skilled investigator. What did you do? What did you find?

GOLDSMITH: So I decided - after years of talking to him after we reconciled, just having casual conversations, Hoffa would come up. The disappearance would come up, and I kind of became convinced that he didn't do it. And the main reason I became convinced was because of the way he revered Hoffa and spoke about Hoffa and also because the circumstances in which he was alleged to have done it - they just didn't add up to me.

So what did I do? I did everything I could. I basically talked to every FBI investigator that ever worked the case, starting with the original four FBI investigators who were on the case - two in Detroit, one in New Jersey, one in New York. I spent a dozen sessions with them. They're extraordinary men, and we actually improbably became friends over the course of our mutual investigations into figuring out what happened, what actually happened in the disappearance.

I read boxes and boxes of government documents, some of which are publicly available redacted, a lot of which I got my hands on through various sources that have never been revealed and talked about before. I spoke to the FBI investigator who was on the case for 15 years for the longest, and I followed up leads that suggested that the FBI, starting in the '90s, started to think that Chuckie perhaps wasn't involved. So I followed that lead up, and it turned out when I done that, I learned more about why the FBI thought that Chuckie maybe had not done it and, indeed, had concluded that he had not done it and they had reason to think someone else did.

So I pieced a whole bunch of evidence together. I figured out the holes in the circumstantial case against him, and I came up with a whole bunch of reasons why I didn't think he was able to have done what he was alleged to have done that day on July 30, 1975. And finally, I think the clinching piece of evidence, if you want to call it that, is the FBI itself and several agents and U.S. attorneys - assisting U.S. attorneys that I talked to were completely convinced he was innocent. Indeed, they were on the verge of exonerating him.

DAVIES: Jack Goldsmith's new book is called "In Hoffa's Shadow." We'll continue our conversation in just a moment. This is FRESH AIR.


DAVIES: This is FRESH AIR, and we're speaking with Jack Goldsmith. He's a law professor at Harvard University, and his new memoir focuses on the story of his stepfather Chuck O'Brien, who had a very close connection to labor leader Jimmy Hoffa, and he was suspected for many years of being connected to Hoffa's 1975 disappearance. Goldsmith's new book is called "In Hoffa's Shadow: A Stepfather, A Disappearance In Detroit, And My Search For The Truth."

You're now convinced, and many others, that Chuckie was not complicit in Hoffa's disappearance, but you always believed that he probably does know things about what happened. What did you get him to tell you?

GOLDSMITH: So one of the themes of the book is Chuckie's struggles with omerta, and omerta is the code of silence that is one of the defining commitments in the Italian syndicate. And Chuckie was not a member of the Mafia. He was half-Sicilian and half-Irish, so therefore, he couldn't be a member. But he always completely imbibed Sicilian values, as he put it, and he completely adhered to omerta. And he did so because his mother and uncle Tony Giacalone and all the people on the mafia side of his life had not convinced him. This is just the way of the world. And so this was very important for him not to tell about things he wasn't supposed to talk about.

On the other hand, he knew that he needed to be truthful with me, and he knew that I wanted to write a credible book, so he ended up telling me quite a lot about a lot of things but not everything. He didn't tell me, I'm convinced, everything he knew. But he did tell me quite a lot about especially the run up to the disappearance and, I think, the basic conspiracy of the disappearance. And he told me enough, certainly, to convince me of what the horrible situation he faced after the disappearance - in between the government, the Hoffa family and the mob, he was in an impossible position there - and enough to convince me that he, in fact, didn't pick up Hoffa that day.

DAVIES: Right. How do you regard his insistence on going to his grave with these secrets?

GOLDSMITH: Well, I don't know how many secrets he's taking to his grave, but he is certainly taking some secrets to his grave, and I'm of two minds about it. Mostly, I certainly didn't try to and didn't push him to tell me things he didn't want to tell me. And we had this very complicated relationship over years and years of talking where he was trying his best to tell me things and sometimes indirectly pointing to things, and I was asking question after question, interrogating him. But I was always not wanting to go too far because I didn't want him to cross any lines he wasn't supposed to cross. So we're playing this dance for years that we're both aware of.

And for most of the time, especially starting out, I thought that his commitment to omerta was self-serving and probably unprincipled, and I didn't really understand it. But I have to say, by the end, I did come to understand it, at least in this sense. For Chuckie, it was the - really, in some ways, the most important thing in his life. It was the principle of honor that he grew up with and that he always adhered to, and frankly, it was the thing he held on to for 45 years after the disappearance when he could have said other things to sort of exonerate himself and didn't.

DAVIES: Do you think that the Hoffa case will ever be solved?

GOLDSMITH: I'm not sure it'll ever be solved in the sense that we will find Hoffa's body or remains or that we'll know exactly what happened in the parking lot in - outside of the Machus Red Fox on July 30, 1975, what happened there. The FBI currently has what it thinks is a new theory of the case that it believes. It believes that Hoffa was picked up by Vito Giacalone, who was the brother of Anthony Giacalone. And it believes it knows who the murderer is, and...

DAVIES: That's the brother of your Uncle Tony.

GOLDSMITH: Yes. Vito Giacalone, otherwise known as Billy, was the brother of Uncle Tony. I never met Vito. And it believes it knows who the killer was. He was someone who was a low-level organized crime figure in the '70s who rose to pretty significant prominence in the family and who died earlier this year.

I don't name the person in the book because I don't know what the basis of the FBI's judgment is. It told me - several people told me that they have surveillance evidence and informant evidence that makes it think that this is what actually happened to Hoffa or at least who was involved. Beyond that, I don't know, and I don't think the FBI has a clinching case. I think they have, basically, information about who they think did it, but not how.

DAVIES: And the - kind of the irony is that in a broader sense, it was sort of clear from the beginning that Hoffa was engaged in a course of conduct trying to return to the presidency of the Teamsters and attacking the then-President Frank Fitzsimmons and his mob ties and was making enemies.

GOLDSMITH: Yes. He brought this on himself quite literally, and in the book, I give a lot of new detail about the run up to the disappearance. The disappearance, based on everything we know and everything I report in the book, was a perfectly predictable consequence of Hoffa's behavior. He was basically threatening to reveal how the mob infiltrated the Teamsters, and he was threatening that in a credible way, and that's basically why he was killed.

DAVIES: How's Chuckie now?

GOLDSMITH: He's not in great shape. He has a bunch of medical problems, and he goes up and down. He's still with us, but he's not in great shape.

DAVIES: Has he seen and read the book?

GOLDSMITH: He has read the book, yes.

DAVIES: What did he think?

GOLDSMITH: Well, I showed him the book before I decided to publish it. I originally was going to wait until after he passed away to publish it because I was afraid there would be some things in there that he wouldn't like and that even would dishonor him. And at the same time, he really wanted me to publish it before the Scorsese movie came out because he wanted the world to know that he, in fact, did not kill Jimmy Hoffa, did not drive him to his death.

So I decided that I was going to allow him to make the - read the manuscript and decide whether I could publish it or not. I was going to abide by his wishes. I saw him reading parts of the book. I saw him wince a few times. He asked me to take out two or three very small things just out of respect for various people - nothing material to the book.

So that's what I knew before the book was published. He's read it since then. I know he's read it now since it's been published. He's got a variety of emotions about it, different emotions at different times. And he told me he was sorry for being such a pain in the ass by not telling me things.

DAVIES: (Laughter). Well, Jack Goldsmith, thanks so much for speaking with us.

GOLDSMITH: Thank you very much.

GROSS: Jack Goldsmith spoke with FRESH AIR's Dave Davies. Goldsmith's new book is called "In Hoffa's Shadow: A Stepfather, A Disappearance In Detroit, And My Search For The Truth."

Tomorrow on FRESH AIR, my guest will be Conan O'Brien. In addition to his TBS late night show, he has a podcast which is about to start its second season. We'll talk about making changes in his career, trying new things and how, for much of his life, he's been driven by anxiety. I hope you'll join us.


GROSS: FRESH AIR's executive producer is Danny Miller. Our interviews and reviews are produced and edited by Amy Salit, Phyllis Myers, Sam Briger, Lauren Krenzel, Ann Marie Baldonado, Therese Madden, Mooj Zadie, Thea Chaloner, Seth Kelley and Joel Wolfram. I'm Terry Gross.

(SOUNDBITE OF MILES DAVIS' "U'N'I") Transcript provided by NPR, Copyright NPR.

NPR transcripts are created on a rush deadline by an NPR contractor. This text may not be in its final form and may be updated or revised in the future. Accuracy and availability may vary. The authoritative record of NPR’s programming is the audio record.

Fresh AirBooks
Dave Davies is a guest host for NPR's Fresh Air with Terry Gross.