Jason Hartman hosts a Flash Back Friday episode where he hosts investigative reporter, Jon Leiberman. The show centers around his latest book titled Whitey on Trial: Secrets, Corruption, and the Search for Truth. The background is that James “Whitey” Bulger murdered 19 people but there were issues when investigating. The government was very corrupt throughout the entire process. Leiberman explains why Bulger got away with all this murder and how his gang had willing accomplices in the FBI, public servants who not only looked the other way but actually colluded in the crimes. To end the show he discusses his work on the Howard Stern Show.
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Welcome to this week’s edition of flashback Friday, your opportunity to get some good review by listening to episodes from the past that Jason has hand picked to help you today in the present, and propel you into the future. Enjoy.
Announcer 0:14
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Jason Hartman 1:03
Welcome to the holistic survival show. This is your host, Jason Hartman, where we talk about protecting the people places and profits you care about in these uncertain times. We have a great interview for you today. And we will be back with that in less than 60 seconds on the holistic survival show. And by the way, be sure to visit our website at holistic survival calm, you can subscribe to our blog, which is totally free has loads of great information and there’s just a lot of good content for you on the site. So make sure you take advantage of that at holistic survival.com. We’ll be right back. It’s my pleasure to welcome john Lieberman to the show. He’s an investigative reporter for the Howard Stern Show on Sirius XM and host of Lieberman Live at Five, a weekly news radio show airing on Howard one on one crime contributor for CNN and HLN. And he’s got an interesting new book about whitey bolter, john, welcome. How are you?
Jon Leiberman 2:00
Hey, Jason, thanks for having me. Doing well. How you doing?
Jason Hartman 2:02
Yeah, good. It’s great to have you on the show. You’re coming to us today from New York City. Right? Indeed, New York City where there is no and and more bad weather. Yeah. And you’re right in the Sirius XM offices now I believe. Right? That’s right. We’re right in midtown Manhattan, or should I say studio?
Jon Leiberman 2:20
Maybe a little bit of both a little bit of both offices in studio. Good stuff.
Jason Hartman 2:24
Well, tell us what you’re working on nowadays. JOHN?
Jon Leiberman 2:27
Well, our new book lady on trial, you know, is kind of a labor of love. I was national correspondent at America’s Most Wanted for seven years. And while I was there with Fox, I went around the world with the FBI whitey Bolger Task Force searching for way. Of course, it turns out he was hiding in plain sight in California the whole time. But regardless, I teamed up with a Boston attorney Margaret McLean, to write this book, which, you know, Chronicles, I would say a once in a lifetime type trial, you know, 19 murders pinned on YT convicted killers coming face to face in the courtroom, white even writing us a letter for our book. So it’s really one of those cases that just doesn’t come along very often. And and we spell it out in our book while you’re on trial.
Jason Hartman 3:13
And so we is what’s the government corruption angle, though?
Jon Leiberman 3:17
Well, look, the reality is that many in the government in the Department of Justice knew exactly what whitey Bolger was doing. And they look the other way. And by doing I mean, brutal killings, amassing millions of dollars into drug trade on the streets of South Boston, and really ruling that entire area, out of fear. And the reality is that some of the corruption came out in the trial. But there, there are other hints of it, that we still haven’t been able to get a full grasp of. And the reality is that, yes, informants are incredibly important when you’re talking about law enforcement when you’re talking about gathering intelligence on crime both domestically and abroad. But the question is, how far can you allow your informants to go? And in this case, I would argue, and I think many would agree that whitey Bolger James White bolter, was allowed to go too far. And and so what is the reason that the government acted this way?
Jason Hartman 4:20
I mean, I guess you’ll have to speculate as to the reasoning, because you don’t know for sure, probably.
Jon Leiberman 4:24
But no, no, I can tell you that I can tell you the reason. I mean, the reality was twofold. One is that whitey had, you know at least one agent john Connally in his pocket. They were childhood friends, and currently currently sitting in prison in connection with one of the murders in this case. And in fact, in our book, we have an exclusive interview with john Connally from prison, the only one that he done, in which he claims that he was simply the Fall Guy, the scapegoat, but that the corruption went much higher than him in the Department of Justice. So one reason of course, as I said, is white. He was friends with this agent. Another reason that the government was hungry to get information about the Italian Mafia. And they felt as if whitey Bolger leaving the Irish American mafia in South Boston could help provide them with Intel on on the, on the Italian Mafia, which they wanted so badly because a lot of people’s careers hinged on bringing down the Italian Mafia in the 70s 80s and early 90s. And so they would basically do anything to get that sort of information.
Jason Hartman 5:30
Yeah, unbelievable. You know, it’s just, I mean, you know, any thoughts on how we can end or attack this kind of this kind of dirty dealing? that’s going on inside the government? You know, so people there can be real justice?
Jon Leiberman 5:48
Yeah, I mean, that’s the billion dollar question. But I do think that in this day and age, with 24 hour news cycles, and a lot of different internet sites, I mean, I do think the watchdog function of the media hasn’t gone away. And in fact, in some ways, it’s actually more than it’s ever been, because now you have, you know, citizen journalists and a whole bunch of different people, you know, looking at but one one misconception about whitey two was that he and his crew simply killed other monsters. Well, the reality is, they did not. And we tell a story in the book of a woman named Diane Sussman. It took the stand in whities trial. And she describes how she was on a second or third date with a guy named Louis and she and Mui were in a car with a third person the next day, you know, the car is riddled with bullets. She is badly wounded. Louis, the guy who she was on the second or third date with was paralyzed. And the third guy, Mr. Milano was murdered. And this was completely a case of mistaken identity. Bolger and his crew at the wrong people. And the story that we tell in the book is how, over the next 30 years, Diane Susskind who was in her early 20s, then never missed a month, Vick going back to visit Louis, the guy that she was on the date with so she would go on to get married, have children have a family in their career, but she would always be tied to this man who she was wounded in the car with on her second or third day. And to me, you know, it shows kind of the power of the human spirit in in the context of such a dark, dark event. And it really was an amazing story.
Jason Hartman 7:30
Yeah, that’s that’s just incredible. Okay, well, now, you do I mean, you do investigative stories for Howard Stern. That’s
Jon Leiberman 7:41
pretty new. I do. I do a little bit of everything. I do news for the Howard Stern Show as you as you touched on. And then of course, I host my own show on Sirius XM club Lieberman live, which is every day, and then I’m a crime contributor for CNN HLN, which is CNNs sister network and then for a for a website called wild about trial as well. And I blogged for the Huffington Post for their crime section. So my career has been based, you know, very much on covering crime and, and digging into and investigating criminals.
Jason Hartman 8:18
Who else have you investigated? You know, what are some of the more interesting, interesting ones? I mean, you know, you’re deep into the whitey Bolger thing, because because you did a book on it. But there’s got to be some other fascinating cases, right?
Jon Leiberman 8:29
Well, for seven years at America’s Most Wanted, I mean, I was on the road seven days a week. Wow, chasing chasing down fugitives. You know, I’ve done cases of mass murder of prison escapees of rapists of bank robbers. You know, I’ve come face to face with probably upwards of three dozen convicted killers that I’ve interviewed in prison. And look, the one commonality is everybody has a justification. Everybody says they have a reason why they kill
Jason Hartman 9:00
or don’t they? Don’t they just first say they’re not guilty. I’m in the prisons are full of innocent people. I know.
Jon Leiberman 9:07
Yeah. But surprised. Surprisingly, surprisingly, some of them say that they’re not guilty. But others say yeah, I get it. And here’s why. And they always have a justification. It’s mainly the sex offenders that actually that always sort of have a rationale for why they did what they did. They perpetrated this rape because of X, Y, and Z. And that’s really sickening. In some ways, you know, my career, I’ve found that sex offenders are even more offensive in some cases, then brutal killers. Yeah, because of the recidivism and, and the like,
Jason Hartman 9:41
Yeah, well, the ads for didn’t give us some examples of these justifications. I mean, I can’t I can’t imagine you could justify any of this stuff. But what do they say?
Jon Leiberman 9:51
Oh, well, I mean, look, domestic murders are the number one type of murder that we see in this country, you know, murders by spouses or boyfriends or girlfriends. So you know, I’ve heard every excuse in the book, you know, she, you know, she demean me he and it goes both ways to Frankly, I mean, I think cases of men killing women and women killing men, and, you know, and and, you know, relationships are so volatile that, you know, I’ve heard every excuse in the book in that regard. And, you know, in sex offenders truly think that, you know, a lot of cases that their victims are asking for it, number one, and number two, that they just have an impulse that they can’t control. And they, they don’t see it in black and white terms, like many of us do, you know, they see a lot of gray and what is appropriate and inappropriate, you know, with children, that’s been my experience. What do we do with these guys? I mean, do we double tap them? I I kind of wondered, what is the deal? We never hear much about it. Like, what? What about chemical castration? I mean, does that just not work that well? Or? Well, it’s try, you know, you have so many civil libertarians who fight against that. I mean, I remember when I was a reporter in New Mexico, there was a big push for chemical castration, but it kept getting defeated and defeated. Look, the reality is that we’re stuck in a terrible situation, because if it were up to me, I’d say, for sex offenders, you know, you lock them up and throw away the key, the problem is that that’s not the reality and they get out of jail at some point. So then the question becomes, how do you rehabilitate them? when they’re in? You know, how do you try to rehabilitate them through treatment, I don’t personally think the treatment works. But if you if you believe, like I do, the treatment doesn’t work, then you also have to believe that simply they’re going to be incarcerated for a finite amount of time, then they’re going to be released and do it again, which is what I believe, you know, and so it’s so it’s a struggle. I mean, but I hate absolutely hate to see when sex offenders are released, and they don’t register as sex offenders. And they end up perpetrating again. And they do and they do because they, they prey on young children. Yeah, that’s
Jason Hartman 11:54
that’s just that’s just scary. I mean, it’s disgusting, obviously. But just seems like these guys would just volunteer for this stuff. I don’t know why there’s a civil libertarian issue here. I mean, you know, I’m sure the ACLU crowd cries foul about it. And sometimes I agree with the ACLU, but not always, probably, mostly not. But I mean, would it be an issue of is it foolproof? Like, if they do chemical castration, Could these guys be released? I mean, wouldn’t I, gosh, if I were in that spend your life in prison or becoming like chemically castrated and be released after, you know, a shorter sentence? Wouldn’t they all choose release? And I mean, it was it’s foolproof it, you know, it seems like you give them a choice. They don’t have to do it.
Jon Leiberman 12:40
Yeah, but criminals don’t get a choice. That’s the thing.
Jason Hartman 12:43
Your choice, it’s 1000 choice, right? It’s a look, if you want to get out early, because we’ve got overcrowding, and we’ve got, you know, a problem paying for all these prisons, it’s very expensive to incarcerate people, if you want to get out on the minimum side of your sentence of, say, seven years or whatever, right versus 20 years. I mean, that’s the decision.
Jon Leiberman 13:06
Yeah, I before it, I mean, look, those who those who argue against it, say that once you’ve done your time, and you’re going to be released, you know, you’ve done your time, and you deserve to kind of get a fresh slate. I don’t, you know, personally subscribed to that theory, but that’s but those who support that do. Yeah, just kind of wondering. I mean, you know, there seems like there must be some logic. But yeah, I can imagine these guys are just incredibly manipulative. Any other really stunning excuses. And that’s what I want to call them not reasons. Or, you know, just these guys have made. Yeah, because they’re crying. Well, I remember, I remember sitting down with a, with a convicted sex offender who reoffended, he had a bunch of victims down in Texas. And I remember sitting across from him kind of reading the victim statement out loud to him. And, you know, and I ended after reading up a laundry list of what this guy done. I said, so do you feel as if any of this is inappropriate? And he looked at me in the eye? And he said, it depends what your definition of inappropriate. I mean, and that’s how he, you know, I just listed off a laundry list of some of the, you know, grossest acts that one could perpetrate particularly against a child. And so then to, you know, to have his report be, it depends what you define as inappropriate. I mean, gives you a good glimpse into the mind of predator, right?
Jason Hartman 14:26
Yeah, it sure does. But I just have to say, you know, for the record, I mean, you go to Middle Eastern countries, and I mean, it’s, I saw this disgusting video, I couldn’t believe it. It’s on YouTube, and it was about some Middle Eastern country and all these men marrying these kids that are they’re so young, I mean, it’s unbelievable five year olds. It’s just unbelievable. And you know, where there were there’s no age of consent. There’s no protection whatsoever. No, I know. I can’t believe that, you know. And so, you know, you put that guy over there and he can just lawfully do anything he wants, right?
Jon Leiberman 15:09
That’s right. I I remember when I was in America’s most one, we did a case of a of a predator here who fled to India to an area of India where they were sex tourism is a huge trade. And it’s just as you just mentioned, and it’s just that the car bill, look, our system is flawed, but it’s still the best criminal justice system in the world, in my opinion.
Jason Hartman 15:30
Now. Yeah, very interesting. Okay. So any other crimes or just interesting stories are? Yeah, I kind of like to I don’t know why I’m curious about this. But it’s a morbid curiosity. How does some of these guys get away? Like, whenever I hear about one of these there, there was that show? I never got into it. But I know a lot of people did Prison Break. I’m thinking how do they I mean, these modern prisons are so good. Compared to
Jon Leiberman 15:55
all the techniques. You can have all the security measures in the world, all the technology in the world and most escapes come down to two things, either, either faulty technology, meaning that alarms when doors weren’t working, or something like that, or more likely help from the inside. Yeah, I mean,
Jason Hartman 16:14
the reality of corruption again,
Jon Leiberman 16:16
it’s one of the I did a case in Indiana where a woman named Sarah Pender escaped. She was a double murder in for 100 years, and she escaped and how did she escape? She escaped by befriending a jail corrections officer starting to sleep with him. And you know, and and, and there you go. He said, You know, he actually helped her escape, she went on the run, she was on the run for six months before it tipped into America’s knows why caught her. So I mean, the reality is, again, and I’m not suggesting that every Correctional Facility shouldn’t do everything they can from a technological standpoint. But look, I mean, I I actually just talked to a jailbird the other day, who told me that because of budget cuts, you know, they had nobody manning the the towers inside the jail. So in other words, it was just a dummy. It was a dummy up there, there were no armed guards, manning the towers, you know, looking, you know, looking out onto the, onto the facility, and that’s more and more common. So many security cameras aren’t manned. You would be surprised. So many security cameras aren’t man, they don’t record video, they’re just there as a deterrent. But when push comes to shove, I’ve seen I’ve covered so many cases of kids who were snatched where, you know, yeah, their security cameras either on the side of a building or or somewhere on the street corner, but either they were broken, or they never rolled paid. Or you know, so I mean, you know, unfortunately, nothing is foolproof.
Jason Hartman 17:43
What do you do? Do you deal with white collar crime?
Jon Leiberman 17:46
I’ve covered everything. Yeah, I mean, I’ve covered everything you look at the Bernie Madoff so the world you know, speaking of white collar crime, and build bilking people out of a lot of money, I did a I did a case again, when I was in America is most one of a guy who preyed on the disabled and actually was a financial guy, but ended up bilking disabled people out of millions of dollars and then going on the run, he actually has not been caught to my knowledge. So look, bad guys come in all shapes, sizes, colors, religions, they just do.
Jason Hartman 18:16
What do you think about prison overcrowding? You know, we were talking about these guys getting out of prison and the budget cuts. And on one hand, I want to say let’s be tough on crime. But on the other hand, I think prisons, it’s just become a business in this country. I mean, we’ve got the highest incarceration rate of any industrialized country, I know that maybe the highest incarceration rate in the world, I’m not sure. But this is just crazy. I mean, you know, like Alex Jones has that website prison planet, and you’re thinking that that’s really what this country has become?
Jon Leiberman 18:48
Well, you know, part of that is true. And the reality is a private companies run a lot of our jails a lot of our prisons now, and they are for profit companies. However, you know, the decision was made to hand many of our needs over to these companies, because they can do it more cost effectively than the government can do it. So I don’t know that necessarily. It’s whether it’s a private or public facility, but more so yeah, I think we lock up many, many minor drug offenders shouldn’t be, you know, shouldn’t be in jail shouldn’t be in detention centers. I mean, prison should be reserved, in my opinion for you know, kind of the worst of the worst, anybody with a gun crime, a sex crime, you know, those sorts of crime? victim crimes, right? victimless crime.
Jason Hartman 19:33
Right. Exactly. Exactly. So I got to ask you, then, because we talked about a lot about the sex offender crimes, you probably think that, you know, at least maybe marijuana should be legalized? I would guess?
Jon Leiberman 19:46
Well, look, I think that the war on drugs has been, you know, a tremendous failure. I think most people can agree on that. I agree on that, by the way, that look, that being said, I mean, I’ve been getting to our borders many times and you know, You can, you know, you most of our borders, people think that there’s some big walls separating our countries and and look, the reality is that most of our borders especially the one that the ones that I don’t understand, yeah, New Mexico and Arizona, those are the borders I’ve been to with Mexico firsthand. You just walk across I mean, nobody is, you know. So I think that the the flow, it’s awfully difficult to stop the flow of drugs into our country. So you know how
Jason Hartman 20:27
to stop them is make it legal, then there’s no business forum?
Jon Leiberman 20:31
Well, that’s right. Unfortunately, if you legalize it, you are then accepting that you’re essentially accepting that it’s going to be here. And we have to find a way to regulate it, if you can, you know, the government hasn’t been all that effective in regulating most industries. So I’m not quite sure, I’m not quite sure that they could regulate the drug industry. But certainly, is it time to try something new? Maybe it is?
Jason Hartman 20:54
Well, I don’t know what happened. And I’m going to be interested to see in a year, a couple of years, the stories of Colorado and Washington State, you know, who have legalized marijuana, because I mean, my assumption, although I do not even know this, is it must be a lot less expensive to just go into one of these stores and buy it, you know, where it’s legal, right? I assume that, I assume that they take the money out of it, when it becomes unprofitable, then all of the black market goes away, all of the drug trafficking goes away, because it’s just not it’s not profitable. So it’s not an issue really, of the government regulating it so much as just plain and simple free market economics. It gets cheap, because it’s legal.
Jon Leiberman 21:36
Right. And it’ll be interesting. It certainly will be interesting to see what happens in Colorado and Washington state for sure. As kind of the guinea pigs for this project.
Jason Hartman 21:44
Right. Right. And and that wanted, I mean, I want to kind of wrap circle back to a couple other things that you’re working on. But But I just wanted to ask you on that note, when we’ve got these private prisons, where we’ve got, you know, stories we hear now, and then they’re not super common, but of the prison, the prisons have lobbies that are lobbying to make everything in America illegal. You know, when the lobbyists go, and they go under the guise of Let’s be tough on crime, you know, let’s lower the the drunk driving standard even more, because it becomes this business. It becomes lucrative. And so then you look at the the whole issue, and I’ve kind of wondered about it lately of prostitution. I mean, we’ve got this I did a show on sex trafficking. You talk about disgusting. I mean, the Human trafficking is, that’s far worse than some predator who has a couple of victims. I mean, this is a this is a business of global rights. Right. So yeah, I you know, it makes me think, you know, if you want to solve it make it unprofitable for these scumbags just destroy their business. I mean, I doubt there’s any human trafficking going on in Amsterdam, for example, right? Because, you know, it’s legal.
Jon Leiberman 22:54
So, right. Now, it’s not it’s definitely it’s an interesting way to look at it and human trafficking, and look what happened during the Superbowl. I mean, so you know, I, you know, and and frankly, a lot of people dismiss it, because they say, well, these are, these are at risk youth anyway. Well, I don’t subscribe to that theory. I think everybody’s equal. And whether you’re an at risk youth from a poor family, or you’re a rich kid, in a great private school, anybody, you know, everybody should be treated equally.
Jason Hartman 23:23
So you’re saying and I didn’t catch this part of the story, that people actually tried to justify that it was okay. Because the victims were at risk youths. Are you kidding? Well,
Jon Leiberman 23:35
that’s because that’s why it doesn’t get as much media attention as, as as other crimes because whether you call it sex trafficking, or you call it forced prostitution, or, you know, it’s all about how you frame it, but that’s certainly why it doesn’t get the kind of media attention that it should, might think. Yeah,
Jason Hartman 23:54
yeah, very interesting. Well, in the whitey Bolger case, just to kind of circle back to that for a moment, what happened to the FBI agents?
Jon Leiberman 24:02
Well, john Conway is serving a prison sentence he’s appealing. And, you know, this is a case where a lot of people got deals, a lot of people got sweetheart deals, to testify with the irony being that none of them ever thought that they would have to come face to face with Wally Bolger in a in a court of law, because nobody in that courtroom ever thought he was going to be caught. So you know, is one of the most fascinating dynamics of the case was watching these old time killers, you know, stared down each other, they hadn’t seen each other for many times, 2025 years. These are men now in their late 70s in their 80s. And to watch that dynamic was quite fascinating. And to watch, you know, there were profanity laced tirade in court between witnesses it was it was fascinating.
Jason Hartman 24:47
Wow, I bet it was, I bet it was. Don’t these guys at that age kind of just lose their Mojo a little bit and
Jon Leiberman 24:54
now because you have pride, it’s all about pride, pride and image and legacy. And everybody in the whitey Bolger case including the FBI are worried about pride, their legacy, how they’ll be, you know, looked at in the future, you know, looking back on these three decades in, in Boston history.
Jason Hartman 25:14
Wow, unbelievable. It’s just an amazing case really an amazing case. JOHN, tell people where they can find you and get the book.
Jon Leiberman 25:22
Yep. Well, thanks so much, Jason, you can go to whitey on trial.com. And you can see everything about the case and and pick up our book. And for any true crime lover out there, I think they’ll enjoy it because this was it was a federal case. So it wasn’t televised, so you can’t see all the action. So the next best thing is to read all the details. And we have all the details in there, including behind the scenes interviews with the jurors and with the attorneys with the witnesses with the killers, a letter from whitey Bolger himself to myself, my co author, so a lot of good stuff in there.
Jason Hartman 25:56
Fantastic. Very interesting. And you also have your website, john lieberman.com, as
Jon Leiberman 26:02
well, right? That’s right. I do you can check that out for all of my other projects.
Jason Hartman 26:07
Fantastic. Well, john Lieberman, thank you so much for joining us today. Very interesting talking about some of these these critical issues. And we’ll hope that getting the word out there about this stuff moves the needle a little bit.
Jon Leiberman 26:17
I enjoyed it. Jason, thanks so much. Thank you.
Jon Leiberman 26:25
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