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If it's eight plus, you are now listening to True Murder, The most shocking killers in true crime history and the authors that have written about them, Gasey, Bundy, Dahmer, The Nightstalker, Dck. Every week, another fascinating author talking about the most shocking and infamous killers in true crime history. True Murder with your host, journalist and author Dan Zufanski, Good evening for
the first time. Boston reporters Casey Sherman and Dave Wedge draw on exclusive interviews and exhaustive investigative reportage to tell the complete story of Whitey Bulger, one of the most notorious crime bosses in American history and a long time
FBI informant. The leader of Boston's Winter Hill Gang and number one on the FBI's most wanted list, Bulger was indicted for nineteen counts of murder, racketeering, narcotics, distribution, and extortion, but it was his sixteen year flight from justice on the eve of his arrest that made him a legend
and exposed deep corruption within the FBI. While other accounts have examined Bulger's crimes, this remarkable chronicle tells the story of his life on the run, his capture, and his eventual murder inside one of America's most dangerous prisons, Misery Mountain,
in two thousand and eighteen. Interweaving the perspectives of Bulger, his family and cohorts, and law enforcement, Hunting Whitey explains how this dangerous criminal a aided capture for nearly two decades and shines a spotlight on the dedicated TOTEM actives, federal agents, and prosecutors involved in bringing him to justice.
It is also a fascinating detailed portrait of both Balger's trial and his time in prison, including shocking new details about his death at Misery Mountain less than twenty four hours after his arrival. Granted access to exclusive prison letters and interviews with dozens of people connected to the case, on both sides, Sherman and Wedge offer a trove of fascinating new stories and create and an incomparable portrait of
one of the most infamous criminals in American history. The book that we're featuring this evening is Hunting Whitey, The inside story of the capture and killing of America's most wanted crime boss, with my special guest journalist and author Dave Wedge, welcome to the program, and thank you very much for a Greenness interview. Dave Wedge Ye good evening, David, Dave.
Going, how you guys doing very good. Thank you very much for this interview. An incredible book, and congratulations on you and Casey Sherman's book here Hunting Whitey remarkable, remarkable book.
And all thank you.
Sorry, go ahead, go ahead. I wanted to say that if we could first tell our audience a little bit about your background and your connection to Boston before we get right into this incredible book. Yeah.
No, So, I've been a journalist for fourteen years at the Boston Herald, and I started writing books with Casey back in twenty thirteen. We wrote a book about the Boston marathon bombings called Boston Strong, and that book actually was used for the movie Patriots Day starring Mark Wahlberg that came out in twenty and seventeen. Since then, Casey and I have written a few other books together, and we did a book about the young man who started the ice Pocket Challenge. His name was Pete Frady's. He
was a kid from Boston and he had als. He unfortunately passed away last fall, but that was quite a project to do too, and then we actually did a book in twenty eighteen about Deflategate and the whole saga there with the NFL versus Tom Brady and the fight between the union, the NFL union, and the league on that. And then you know, so this book here. You know, Casey and I both covered the Whitey Balger case for
many years as journalists in Boston. Case he was an investigated producer at the local CBS affiliate and me at the Boston Herald. And you know, we never really expected to write a book about Whitey Bulger. There have been many books written about his exploits over the years. But when he was murdered in prison back in twenty eighteen, you know, we just kind of thought about it and said, you know what, there's an opportunity here to finished this
story until the final chapter. And that's what we did.
Let's get right to the book itself, and you we jump in and with the reader right away and take you. Take us to February third, two thousand and eight and the first day on the job for Assistant Special Agent in Charge, Noreen Gleason. Tell us a little bit about this meeting and what Noreen's Gleason's job was according to Warrant Bamford, Yeah, so Noreen.
Was was put So, you know, the FBI had long had a White Bulger task force, and over the years that he was on the run, that task force would grow and shrink from time to time based on the special agent in charge and priorities of the office. And obviously, when nine to eleven occurred, the office's mission shifted drastically from you know, fugitive hunting and organized crime to terrorism.
And that's that sort of focus kind of persisted for many, many years in the Boston office, given that, you know, the planes flew out of Logan Airport, so the FBI's resources really needed to be used in that fight against terror.
But there were a lot of agents that still were, you know, really upset about the fact that the office was stained with this appearance of corruption from prior administrations with you know, John Connolly and John Morris and H. Paul Rico and some of the other agents that were
in bed with Whitey Bulger and his crew. And so Noring Gleeson was assigned to this task force, and it was really kind of a you know, no one looked at it as really a good gig at the time, because you know, everyone thought he was never going to be found, and they thought they were chasing Bigfoot, you know, this mythical creature that would never be caught. And but Noring Gleeson jumped onto the team, and you know, she made it her mission that you know, she wanted to change the.
Narrative before we talk about the team that she assembles. Let's you take the reader back and let's take the audience back to this trip that Whitey Bulger and his longtime girlfriend he's never married, but they lived like they were married. That she had four kids from a previous marriage, and they had taken a trip to Europe. Tell us a little bit about this trip as you take us back to Whitey before he went on the run.
So, you know, there's a lot of mystery out there about Whitey Bulger and what he had. You know, what he did and didn't do in his life. One thing for sure, he made millions and millions of dollars through his criminal enterprises, whether it be book making, drug dealing, gun running, extortion, and you know, fraudulent business activities. But you know him and Teresa Stanley, you know they traveled Europe extensively, and Teresa Stanley was his first girlfriend, the
one that he originally went on the run with. And you know, there's a lot of questions as to what he did on these trips around the world. A lot of people think and the FBI seems to have believed that he was stashing money in safety deposit boxes around the world. There was a trip to England where he is believed to have put some money into a safety deposit box near Piccadilly Circus. There's been some stories of him putting money in safety deposit boxes in Ireland as well.
You know, he famously was involved in a gun running scheme with Ireland, so he had very close ties to the IRA and an organized crime in Ireland. So you know, the big question here with Whitey Balder that the remaining mystery is where is that money.
You take us back to December twenty third, nineteen ninety four and again White Bulger leader of the winter Hill Gang in Boston South End, violent Irish mafia and he's out shopping Christmas shopping with Teresa Stanley, but he gets a deeper message from his longtime partner, Kevin Weeks tell us what happened to this meeting.
Yeah, So, you know, Whitey Bulger had several law enforcement, corrupt members of law enforcement on his payroll and at his beck and call. One of them was John Connolly, who grew up in the same South Boston neighborhood as Whitey Bulger and his brother Billy, who was a powerful politician in Massachusetts. He was the president of the Massachusetts Senate and the president of University of Massachusetts. And Kevin Weeks was kind of the go between for Whitey Bulger
and a lot of these corrupt law enforcement folks. And you know, there was a lot of chatter in the media and you know, just in criminal circles that there was indictments coming down against Balder and his crew, you know, sweeping rico cases. You know, people were being arrested and rounded up, and there was a lot of chatter on
the streets that people were talking. And you know, when Kevin Weeks gets that deeper message, it was an alert to Whitey Bulger to let him know that the indictments were coming and it was time for Whitey to put his plan into action, which was to go on the run.
And he had been planning for this moment. Really for many many years through what we just described, you know, you know, leaving money in safety deposit boxes around the world and around the country, and also having cash at hand, guns, fake identities and disguises, and a plan to get out of Dodge.
Whitey has a partner as well of associate named Steve Flemy, and so he contacts him as well and tells him about the indictments, doesn't.
He Yes, So Whitey got the tip from John Conley they were coming down, and he did let Steve Flemy know that that was coming. Steve Flemy was not as lucky as white Balger. He was not able to get out of Dodge in time, and Steve Flemy was rounded up while white he went on the run for sixteen years. Yeah.
Now, when we talked about that trip that I mentioned with Teresa Stanley, the reason for part of one of the reasons for the trip was to strengthen their relationships. What was wrong with their relationship? What had Teresa found out and what was the situation between them?
Yeah, so she knew about Catherine greg and they had had a confrontation the two women where they were basically fighting over Whitey Bulger. You know, and the research that we did for this book and the interviews that we conducted, one thing was very clear to the people that were closest to Whitey and Catherine was that they had a
true love. And you know, while Teresa Stanley spent more time in her life with Bulger than Catherine Gregg had up to this point that we're discussing, he really, I believe, you know, my opinion is that he trusted Catherine Moore and that he actually loved her more. Him and Teresa
had a very volatile relationship. There's a lot of uh, there's a lot of violence in the relationship, a lot of control, and you know, I think a lot of it was centered around the issues here that that he had another woman in his life and that was Catherine greg.
Right when he decides that he needs to go on the run and leave Boston, he doesn't immediately go on the run because he gets this head's up. But what was the situation with Stanley. You talked about that he had more love for Katherine greg But why was it, at least on the surface, the reason why Teresa couldn't join him on the run.
So Teresa had children, and she had family ties and She was not ready to give those up and just go on the run and disappear forever and not see her family and friends anymore. She was She expressed that to Bulger, you know when when this plan was first enacted, and he was furious, obviously, and he brought her back to Boston and he dumped her off and he picked up Catherine Greg under the cover of night. He picked her up in Boston and he took her on the
run with him and left Teresa Stanley behind forever. And it was It's a weird thing, you know, because I think Catherine Greg feels like, you know, felt like at that moment that she had won. You know, she won the battle for Bulger and she was now his number one mall for lack of a better term.
You talk about his age and the age difference between them. What is the age difference between them? And also you you write about a son that he had with a former relationship, Douglas Glenn Sear. Tell us what happened there and his reaction to that.
Yeah, so White and Catherine. There's there's a big age difference there. I believe it's about twenty years. But yeah, you know, one thing, a lot of people don't know about Whitey Bulger is. You know, he was never married. You know, he Teresa Stanley was could be kind of considered like his common law wife, but they never formally married. They never had any children, but white he did have a child. He had a boy, and and that boy got very sick, he had high fever and uh and
the kid ended up passing away in the hospital. And that you know, a lot of people that know Bulger in his story point to that loss of his sons as a pivotal moment in his life that really pushed him from being just another organized crime figure to really be in this ruthless, ruthless gangster that was really heartless and had no no mercy, no moral compass anymore.
You know.
And not only did he play law enforcement like a fiddle, but he would really go out of his way to exact revenge on people, particularly cruel to women. Throughout the rest of his life. He blamed the mother of his son for that boy's death. He blamed her for not helping the kid get medical help fast enough. And it really changed the He was on a bad path anyway, but I think it really pushed him further into the Abyss.
You're right that Kevin Weeks is a free man, but Steve Flemy is in jail, so hesits him business them This isn't very often. What had Whitey done to alter his appearance of anything? And what was the situation in terms of what the FBI contained in terms of photos.
Yeah, so Bulger when he went on the run was a very different appearing man than he was in the surveillance photos that the FBI had of him. Remember that, you know he went on the run in nineteen ninety five. Most of the surveillance photos that the FBI had of him were from the seventies and eighties and even sixties. And you know, his mug shots were ancient. They were from the fifties and sixties. So Whitey Bulger was very smart. He hated having his picture taken. He avoided it. There
there aren't many pictures of him that exist. They were able to find a couple. There's there's one infamous one that we have in our book from Christening of John Moderano's son. John Monerano was one of Whitey's and forces. Who's a guy that killed over twenty people for the crew. And there's a picture that we have in the book of Bulger holding John Monarano's son at a christening. That's one of the last known photos of Bulger from before
he went on the run. So when he went on the run, you know he was he was notoriously wore a bucket cap, sunglasses, grew a beard, and he just appeared like an old, older, you know, retiree that was kind of in these you know, Southern states and and and you know, tropical climates he kind of fit in. He hit playing site.
What was the alias that he used? Uh that Teresa knew of as well, that Catherine and Whitey were using. What was the alias that they were using on the run?
So the first alias that he used was Thomas Baxter and that that name almost got him caught in New York because you know, the FBI was able to and the the you know, the law enforcement that was that was trailing and was able to find that that was a fake name, and they were able to tact the track to a vehicle. But whye he was managed to stay a step ahead of them every step of the way.
There's a lot of questions as to why that happened, whether or not early in the investigation if he was getting, you know, continuing to get help from law enforcement, from you know, the likes of John Connolly. And you know, it appears that that is the case, that early in his flight from justice, that Whitey was continuing to get inside information from Lauren Wilson authorities. So Bulger changed that name,
and he used several different names. One name that he used was James Lawler, and then there was another one that he ended up using at the end, which was Charles Gasco. And he had used a variation of that at times as well, Charles Gasca with an A on the end. But in the end, when him and Catherine greg were in Santa Monica, they were Charlie and Carol Gasco and that's that's how people knew them out there.
Now, at the same time, you've talked about with Norien Gleason assembling a team to start re evaluating and re invigorating this this mission to try to find Whitey Bulger. So what was the what was the wisdom at the time where he might have gone? He had all this money, they reckoned, But where did the FBI believe he had gone to?
Likely, Well, there were you know, there were sightings all over the world of Bulger and Catherine greg and he in fact holds the unique distinction of being the most featured criminal ever on the old show America's Most Wanted. He was on there more than a dozen times and it generated literally thousands of thousands of tips over the year. So I said earlier that you know, it wasn't really looked at as a plum gig to be in the
Whitey Bulger Task Force. But there was a time when it was looked at as a plum gig, not because you had the opportunity to catch white Bulger, but because you got to travel the world. And a lot of the agents would joke about it that, you know, he joined the Bulger Task Force and see the world. You know, agents were going to Cuba, they were going to Ireland, they were going to Aruba, they were going to remote Caribbean islands. They were sent to Italy to check out
these and all of them proved to be false. None of them proved to be accurate. And in fact, it appears that Whitey Bulger never left the country. That's actually you know, we have some letters, exclusive letters that have never been seen before. In the book where he says that you know, he never left the country and they were chasing his ghost.
I talked about this team that was assembled by Gleason with a guy named Tommy McDonald that she knew from the past, and a couple other people that she agents that she trusted. What was a person named Charles gian Turco was one of these people. Now, what was the mindset that these people put together and what was the the I guess the pivotal decision that they made in terms of the new direction for this this hunt for Whitey.
Yeah, well, I think all these agents came in with the same mindset, which was, you know, enough's enough. You know, the Bureau has been smeared enough over this case. Let's find a way to end this once and for all. And the pivotal decision that was made was to stop chasing Whitey and stop chasing Catherine. And that was a decision that was that was made by that group you mentioned,
led by Nora Gleason. And what they did was they started tracking down every bit of information that they could find about Catherine greg And what they found was that she had that she had received extensive plastic surgery and they actually were able to track down her plastic surgeon and get some pictures of her that they later used for a famous public service announcement that was broadcast across the country. And that's really the break in the case
that had never been done before by the FBI. They had never you know, funded their own PSA. They spent fifty thousand dollars to make it with a video company, and then they spent another fifty thousand dollars buying ad time around the country and white Bullsrom himself saw that when he saw that PSA, he looked at Catherine greg and said, this is it.
They also the fortunate thing about this PSA as well, because they had a limited budget, and it had such a limited budget that they couldn't afford to run ads in the Los Angeles because the ad read revenues were so high or the rates were so high. So what happened in terms of this fortunate break as a result of this unique approach with this commercial to try to find Whitey, Well.
Because they used this innovative tactic, you got a lot of media coverage, and that media coverage spread the ad into areas that the FBI couldn't afford to buy ads in. So the Los Angeles market was one of them, and you know, it received pretty widespread coverage in the news
in Los Angeles. And that's how the ultimate final break case came was when one of the residents, a woman from Iceland that lived in the Princess Eugenia Apartments next door to Whitey and Catherine, who she knew as Charles and Carol Gasco, she saw the ad and she called the hotline, and that's how the case really unfolded.
Now you talk about their time, you and Casey chronicle their time in Santa Monica, but before that, there was a close call. They were in Louisiana. So just tell us about this close call and then tell us a little bit more about their life in Santa Monica at this Princess Eugena apartments.
Sure. Yeah, So, you know, as I said before that, you know, it appears that Bulger was still getting some help from law enforcement early in his flight from justice. One of the first places they went after leaving the Northeast was to Grand Isle, Louisiana, and they lived down there in a seaside IU community and they befriended a family down there, the Gatrol family, And we have interviews with the Gatrol family that you know, they they just knew them as this kindly old retired couple that would
you know, spend time with them. They took them shopping. You know, Bulger was very generous. He took their son under his wing and and kind of, uh, you know, tried to teach him life lessons on how to be a man and stay in school and that sort of stuff. And you know, they there was an FBI agent that that got some great information that they were in that area. And the agent actually made it down to Grand Isle
and was was staking out the area. He was unable to get back up from the FBI and he's actually pulled off the case mysteriously. And in that time that he was pulled out of there, he was planning to put together an operation to try to move in and get Bulger. He thought he knew where he was, he was in the right town. But Bulger got the tip again and got out of got out of town before
that arrest was made. And you know, as a result of that, Bulger continued his flight from justice for another, you know, more than ten years, and they migrated west and they landed in Santa Monica, which was somewhere that he had been familiar with. It's interesting, you know the parish in South Boston that he grew up and was known as Saint Monica's and he ends up hiding out in Santa Monica. And he had some relatives that had
lived there in the past. His niece lived there, and they assumed this quiet life of retirees in a nondescript neighborhood and Santa Monica right near Palisades Park, ironically less than a mile from the local police precinct, and there's surveillance cameras on every corner. And he was literally under surveillance the whole time, but no one made him until that ps A was put out.
When we talk about the PSA and also the task force with Norien Gleason and company, that they wanted to focus on Catherine greg But they got a break when we didn't mention this. They got a break from a dentist because they had heard that they were are not a part of me, another dentist, a person a plastic surgeon. Now, what was important about that contact with them, other than the information that she had indeed got plastic surgery. What was the crucial thing that he provided and why.
Yeah, the crucial piece was this plastic surgeon that had treated Katherine greg and actually gave her breast implants. He had multiple pictures of her, and they were very clear, up closed photos, unlike anything that the FBI had before. You know, the pictures that they had of Catherine before were like old family photos. They weren't, you know, up to date. Some of them were kind of grainy, but these were very clear, almost like mug shots, and those
are the ones that they used in the PSAs. And that's really the picture that the woman from Iceland was able to recognize. And you know when she called, she said, I'm not one hundred percent shorts them, I'm two hundred percent sure.
Right now with this information, of course, they have to make sure this is the people, and they find out that these people are like ghosts. They don't have any background information under the alias that they're using at this apartments. So how do they proceed to capture Whitey Bulger and obviously reduce any possibility of anybody getting harmed in the process.
Yeah. So, you know, they knew that Whitey Bulger had an arsenal of weapons, and they assumed that he was ready for war and in fact he was. The fear was always that he would take Catherine hostage and use her as a human shield so he could escape. So when they made the approach to the Princess Eugenia apartments there in Santa Monica, they had to come up with a ruse to lure Whitey Bulger out of the little
apartment there on the third floor. And the way they did that was they had the manager call him and say, Hey, I'm sorry to tell you this, but someone broke into your indo a storage locker. Can you meet me down in the garage, you know, and I'll help you out. And Bulger did not pick up on the suspicious nature
of that request, and he it's funny. We have a great letter in the book that Whitey Bulger, in his own words, describes his arrests there in the garage, and he talks about being in the elevator going down and how quiet it was and he felt like something was off. But even though he says that he didn't pick up on it at the moment, and he walked right into that trap.
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So you know, this was really the trial of the century in Boston. No one expected that this trial would have ever happened. It was held at the Joe Moakley Courthouse on the South Boston Waterfront, which is named after the famous United States Senator Joe Moakley, who grew up in South Boston, not far from where White Ball during and his brother Billy grew up. So the courthouse is a very high security event at the courthouse because it was shortly after the Boston Marathon bombings, so the entire
city was really on a heightened state of alert. And Joe Carson, I have the bomber, the Boston Marathon bomber, the one who survived and was a waiting trial was actually at the courthouse as well when that trial was going on. He was he was being held there. Well, he was a waiting trial. So it was a pretty uh, you know, incredible time in Boston's criminal trial history. The harbor was shut down, there were boats that patrolled with armed officers on them.
Uh.
The perimeter around the courthouse was sealed off with with barricades. There were canine units that patrolled the neighborhoods surrounding the courthouse. So there was a lot of concern for not only terrorism and retaliation against Joe Karsanaya, but also whether or not there would be a hit on a guy like Whitey Bulge's life.
Right now, the prosecution team is Fred Whitechek and Brian Kelly, but they also have the agent Dan Daugherty, State Trooper Steve Johnson, Department of US this investigator Jim Merhra and I R. S Agent Sandy Lemansky putting this whole thing together. Also a person named Prosecutor Hayfer as well.
Yep.
Now, the various charges of racketeering, extortion, and the nineteen murder charges, how were they, What was the strategy in terms of at trial and what were the as you right, the cast of characters that were going to make appearances and including the star witness against Whitey Bulger.
Well, there was you know, there certainly was a cast of characters that came through. It was almost like an episode of this is your life, Whitey Bulger. And I think that's how Bulger looked at it. You know, he sat at the at the defendant table and watched this parade of people from his past come up. You know, you had bookies, you had you know, the drug deal as, you had the relatives of those that he was accused of killing, you had law enforcement folks, you had medical examiners,
and it was it was really uh uh. You know, there were days where it was very arduous and agonizingly in depth, and there were days that it was high theater, and we describe a lot of that in the book, where you know, there was moments where Balder disrupted the courtroom with laughter, bellowing out about you know, little anecdotes that would come out from different witnesses. There was other times where he would trade expletives with his former criminal
cohorts that had now turned on them. And remember, Bulger built a reputation of being this you know kind of noble, valiant gangster. But once it was revealed that he was in fact an FBI informant, a lot of his his criminal partners then turned their back on him and they were no longer afraid to testify against him. Those those those associates included Kevin Weeks, who was really like a
son to Whitey Bulger and was his top henchman. John Moderano, who we mentioned before, who killed at least twenty people, admitted it and served only twelve years for those murders and was released in exchange for his testimony against Whitey Bulger and Steve Flemy, and then also Steve Flemy who also cut a deal to avoid the death penalty in
exchange for his testimony against Whitey Bulger. So you had, you know, really the top three people closest to Bulger throughout his criminal life all testified against him in this case.
And you take the reader right into the courtroom with the testimony of John Martrano, Mara Torano and the things that he not only had witnessed himself in terms of being involved with the murders, but also all kinds of, like you say, vivid stories, and regaled the courtroom with his gangster tales. But basically he was a star witness against for the prosecution against Whitey Bulger, wasn't.
He He was? Yeah, John Monorano is you know, your classic kind of hitman gangster. He's a big, you know, big brawny guy that filled up the witness box and dark hair and dark eyes and talked very candidly about people that he killed over the years for Whitey Bulger,
talked about shootings that he committed with Whitey Bulger. He also, would you know, admitted on the stand that he you know, killed over twenty people and and that he received a reduced sentence in exchange for his cooperation, which speaks to the severity of the case against Whitey Bulger. I mean, if they're gonna cut a deal with a guy who's killed twenty people, white Bulger must have really gone bad person. And that was a loud and clear message to the jury,
I think. During that case, it was also revealed that Moderano sold his life rights for a book that he did with a Boston news columnist, and they also tried to, I guess make a movie out of it, but it never happened, and he received over one hundred thousand dollars for those projects. I mean, he's a guy that you know, served He served only twelve years for twenty murders and he got one hundred thousand dollars on top of it.
Yeah. Some of the most chilling testimony at this trial was from him, though, because he talked about the truly atrocious murder of Flemy, Steve Flemy's step daughter, Deborah Hussey, and also about the murder of his beautiful girlfriend, Debbie Davis, and it really demonstrated and illustrated the evil that personified Whitey Bulger. What did he have to say say about those specific murders that again was sent a chill through the jurors and everyone in the courtroom.
I believe it was Weeks and Flemy that testified about those murders, because John Moderano I don't believe was present at either one of those murders. I may be mistaken on that, but I know that Steve Flemy and Kevin Weeks were present for those murders, and you know they they both. Kevin Weeks was a little wishy washy about it.
He just said that she was strangled in the basement, that he helped to bury her with regard to Deborah Hussey, and he was unclear as to who actually strangled her, whether it was Bulger or Flemy, but the Flemy was clear that it was Bulger that did it and that he was was angry about it. Bulger's contention was that Flemy was the one that did it because he had more to lose. But you know, the theory was that both women knew too much and they were risks, you know,
for for Steve Flemy with Deborah Hussey. She was the daughter of Steve Flemmy's longtime common law wife Mary and Hussy, and Steve Flemy started a relationship with that girl when she was underage. She was only I believe like sixteen or even fifteen, And that was that was something that was discussed at length at the trial, and it was it was creepy, creepy stuff. And you know, the way
that she was murdered was very violent. She was strangled and then she was buried there, you know, in the in the in the basement.
It was strange that you write that some of the people that went to testify against Whitey Bulger he seemed to be friendly with and and even instructed his attorney to do what on there when they testified. This was unusual.
Yeah, yeah, yeah, no, some of them. You know, it's funny. It was almost like Bulger was the puppeteer with his defense team and would kind of instruct which witnesses to
go hard at and which to leave alone. And there were some that Balger would nod and say, hey, good morning, you know, and these guys would go up there and testify about all the stuff that Whitey Bulger did illegally, and Balger would basically call off the attack dogs with his lawyers and just you know, tell them, you know what, don't worry about him, you know, basically because he felt that some of the witnesses against him were people that he liked, frankly, and he didn't really have a problem
with them. They would just answer the questions that they were asked, but they didn't go out of their way to to cross Whitey Bulger. But there were others that he did feel that way about, and he, you know, he made that known in the courtroom.
Sometimes you write that he seemed disinterested in the people, certain people's testimony and the proceedings in general. But there were times when there were outbursts at trial. Tell us about a couple of those outbursts.
Yeah, one occurred with with with Kevin Weeks. You know, again, Kevin Weeks was like a son to Whitey Bulger. And at one point they had a stare down in the courtroom and they swore at each other, explained, exchanged expletives and actually Weeks appeared to challenge him to a fight and and said what are you going to do? You know, And and this was in the middle of the court,
in front of the jury. It was certainly a very explosive moment in the trial to see these two criminal partners who built this criminal empire that resulted in so much death and destruction in Boston for so many years, and now they're sitting having a head to head in the courtroom. It was striking, you know, high theater, as
I discussed. And there was other times that there was a bookie that took the stand and told the story about how Bulger was extorting another bookie in a hotel room and threatened to kill him and uh and it may you know, made some colorful comments about what he was going to do, and Bulger got a real kick out of that. He laughed very loudly, he bellowed and
pounded his fist on the table. He just thought it was, you know, the funniest thing he had heard, and it disrupted the court room and the judge was pretty mad about that. But you know, that's the kind of guy he was. You know, he was brazen when he wanted to be, and he was just mysterious and creepy at other times. But during that trial we saw at all.
With the testimony of a person like Kevin Weeks and others at this trial, what was also established and what we didn't go into, is the connection between Billy Bulger being this very prominent and influential politician in Massachusetts, and also Norma and Gleason and other agents hounding the family at least trying to embarrass the family and trying to find out he get any evidence that Billy and brother Jackie or any family members were in contact with Whitey
on the run. So at the trial there is quite a bit of this established by witnesses. Then embarrassment and an involvement by Bulger's family.
Yeah, absolutely, yeah, absolutely, Well, his brother Jackie Bulger was a court clerk magistrate at one point in his life, and he was actually convicted of aiding and abetting as his brother when he was a fugitive. Billy Bulger was never charged, but you know, a lot of these FBI agents that we interviewed for the book were very clear with us that they wished that he had been and
they think that he should have been. Billy Bulger testified before Congress that he and that he did receive a call from his brother while his brother was a fugitive, at least once. You know, there's a lot of information, you know, from the folks we interviewed that that there was more than just that one call. You know, that that they think that Billy was in touch with his
brother more regularly than he would ever admit. You know, Billy Balger when we interviewed him, was evasive on that topic, but certainly yes, during the trial, there was a lot of testimony that Billy Balder was close with John Connolly and was kind of instrumental in forging that relationship between the corrupt FBI agent John Connolly and his brother Whitey.
And also there was some pretty clear testimony that that some of these agents thought that Billy Balder had a lot more to do with his brother's life was a fugitive than was ever really acknowledged, and they, you know, many of them think that he should have been charged.
Also with for the media and the public, they heard about the FBI disgraced former members Paul Rico, John Morris. So the media and the public and the jurors got to hear about the Chickane every going on in the FBI and all of these disgraced agents and including a state trooper named Schneiderham. So this is what for the first time Boston and residents in the world got to hear the actual truth about this mythological almost folk hero. And it was quite the opposite of the myths, wasn't it.
Yeah.
Absolutely. You know, he was showering these agents and law enforcement offices with gifts over the years, paying them off, bribing them, you know, hanging out with them at fancy dinners, buying them Christmas gifts. Whitey Bulge had is saying that, you know, Christmas is for cops and kids, you know, and he would give them envelopes filled with cash. It was disturbing stuff to hear for anyone that likes to
believe that law enforcement is above reproach. It was not the case in Boston in the seventies and eighties and even into the nineties, when you know these corrupt rogue agents, you know, we're cutting devil's deals with people like white Bulger.
You know.
It was Honestly, I think the prosecutors on the case and the young, newer FBI agents that helped catch Whitey Bulger, I think for them it was cathartic to air it publicly once and for all, get all the facts on the record and clear the air and let people know, Yeah, this happened, and it was unacceptable and despicable and criminal, and we're not going to let it. We're not gonna let it go. We're going to expose it and make sure that everyone's held accountable to Canby. And I think
that was a big part of the trial. The other pieces from Bulger's side. His attorneys absolutely wanted to turn this case into putting the FBI on trial. In fact, they went so far as to try to insinuate that Bulger had immunity from prosecution because of his arrangements with the US Attorney's Office and the FBI. And they also tried to create a fictional narrative that Whitey Bulger was not an informant. You know, they tried to put out there that Bulger never gave the FBI anything of substance.
All he gave them was rumor and innuendo and tips that he had heard from other people, and you know, tips of information that they already knew anyway. So it was just really a ruse to try to appease their client, to make him feel like he wasn't the rat that he was.
You talked about that contention, because that was a big part of the potential or their planned defense, was to say that this Jeremiah O'Sullivan had granted him immunity, so they were hedging their bets. But Judge Casper, I believe, shot that down early. So that was when that was defeated. There wasn't much they could do with that because they could not provide any evidence, any documentation whatsoever of that, and the judge ruled on it accordingly, didn't he Yeah, that's right.
So you know, Bulger's attorneys put forth again this narrative that Bulger met with Jeremiah O'Sullivan. He's deceased now, but he was the district attorney. I'm sorry the US attorney at the time in Boston, and he claims that he cut a deal with Bulger saying, keep feeding us information on the Italian Italian mob and I won't prosecute you for anything. There's no evidence to that agreement. There's there's no paper trail, there's nothing. It was just simply the
words of his attorney. They put in a motion, but there was, you know, no way to ever prove whether or not it was true or not. And ultimately the judge, you know, threw it out as an invalid defense because of that reason, because there was no corroborating evidence that that it was true.
It's very interesting exciting moment in this trial is that a person named Stephen Rakes, one of Bulger's extortion victims, and you say, a potential witness and he'd been tending the trial. What happens to him? And what does it lend people to think about what might have happened.
Yeah, So, so here we are in the middle of the trial of the century in Boston, where you know, there's all sorts of witness intimidation, accusations, and you know, people being killed, you know, bodies being on earthed and lo and behold in the middle of the trial, one of the witnesses and one of the people that a victim, actually someone that Whitey had extorted, a guy named Stipo Rake. Stephen Rakes, turns up dead and Stephen Rakes was a
He was murdered. He was found on the side of a road in a suburb of Boston during the trial. And when that happened, it sent shockwaves through the media and through the general public, and it just had everyone saying there for a couple of days, jeez, does Whitey Ball just still have the reach? Can he still you know, get outside of the prison and reach out for me on the walls and have someone killed, because Rakes was
set to testify in the trial. But it quickly was investigated by the police, and to their credit, they shot that down pretty quickly during the trial and said this is unrelated to the trial. What actually happened was Rakes had a dispute, a business dispute with another gentleman, and the guy actually had poisoned Rakes's coffee and and that's how he was murdered. And it was it was put out there pretty quickly that it had nothing to do with the Bulger trial, and.
That guy was that guy was convicted that life.
You know, it was a crazy story. It was a really it really was a wild couple of days there in the trial when that happened, and I think it scared some of the jurors for a few minutes.
Absolutely, Yeah, absolutely. Now the prosecution has a difficult time getting convictions on all of the murders despite all this eyewitness to themoni from Flemy and Weeks and other testimony that seemed to corroborate those indictments. But tell us what happens in terms of the actual indictments that were successful out of those nineteen murders.
Yeah, So they ended up convicting Balger on eleven of nineteen murders, and then there were two that there was no finding, one of them being Debbie Davis, which was very upsetting to the Davis family because at the very least Bulger was there and commissioned that murder, which should be enough for a murder conviction. Is as you know, your listeners know that you don't have to actually be the person that kills the person in order to be
convicted of murder. If you participate or facilitate the killing, then you are guilty of murder if that can be proven, and the Davis family certainly thought at least that was proven, but beyond that, they believed that it was proven that Bulger was the one that actually strangled her. So that was a real and the prosecutor taught to us about
that for the book. The prosecutors found that to be very disappointing as well, that the jury did not find him guilty of that murder because they believed that they proved that beyond a reasonable doubt. But you know, the jury spoke.
What was the end result in terms of the sentencing and where does Whitey Bulger head to in terms of prison.
So he was convicted of those eleven murders and also you know, a slew of gun and racketeering charges, extortion, drug trafficking, all sorts of stuff, and he got multiple life sentences without parole per the law. He sent off first to be classified and then he's sent to a prison out in Tucson, Arizona, where you know, he walks into this prison and he's suddenly, you know, the most
notorious inmate in there. He had a target on his back from day one, and in fact, we report in the book for the first time that there wasn't a tempt on his life. I don't want to get into too any details on it. I think people will get a lot out of reading that part of the book. And then after that happens, he's he's moved to a prison in Florida where he has more troubles.
What about Catherine Greg? What's her sentence and where does she go?
So Catherine Greg had a separate trial and she was convicted of harboring a fugitive and aiding in a betting a fugitive. So she was given I believe the sentence was eight years, and she was sent to a female, a women's prison, federal prison out and I believe it's in Wisconsin. I'm pretty sure. But she, you know, she served her time and actually she's she's since been released and she was she was transferred to a halfway house here in Massachusetts last year, and then she was subsequently
released and now she's out. He's living just south of Boston. Was actually a member of Bulger's family.
Incredible, what was the They had an opportunity to correspond and communicate through the help of a first or attorney and then later a psychologist and you were maybe to some of that information and some of that correspondence tell us about their relationship once they're incarcerated, what does that look like.
So Bulger was clear when he was arrested that he said he would accept the death penalty if it meant that he could have Catherine released. He tells people in the letters that we have in the book that you know, she didn't deserve to be punished. She didn't do anything wrong all. Her only crime was loving him, you know. And he said that she didn't do anything to keep him,
you know, to to facilitate his criminal career. So you know, once they get into their separate prisons, you know, they obviously they had been on the run, spending every waking moment together for sixteen years. He missed her frankly, and his lawyer felt bad for him and allowed him to write letters to Catherine and allowed Catherine to read them
and send them back and forth. And the lawyer provided that cornduit for them, and he said that, you know, Bulger was very emotional when he was reading these letters. I mean, he you know, one thing's clear from our research and the letters that we have was that Bulger's love for her was was very profound, you know, and he expressed that frequently in these letters.
You talk about. By the time he gets the Coleman Correctional Complex, there is Hollywood buzzing again. Hollywood had made a movie Martin Scorsese called it Departed, which is the fictionalization of the Irish mob in Boston. Yes, you could call it that. And but there was Hollywood making a movie with Johnny Depp I believe, called Black Mass. Maybe Matt Damon was involved. Tell us a little bit about this venture from Hollywood and who participated.
Yeah, so you know, Bulger talked in letters that we have in the book about the Black Mass process, and he talked about, uh, you know, Johnny Depp wanting to meet with him and play him in the in the movie. But I you know, he mentions Ben Affleck and having some involvement, and you know, but Bulger did not want to participate with that project because he didn't like the Boston Globe, which is the newspaper where the writers of the book Black Mass were employed. He hated the Globe,
He hated the writers who wrote Black Mass. He he trashed the book in his in his letters, said that you know it was fiction and they got it all wrong and all this stuff. But so it's kind of funny that, you know, Johnny Depp wanted to meet with him and Bulger refused to take that meeting.
What age is Whitey Bulger? Once he gets the Coleman Correctional Complex and you talk about the care level just the categorization of inmates, tell us a little bit about care level three and how is he considered in terms of risk.
So when Bulger gets to Coleman, he by that time he's had multiple heart attackses on multiple medications. He's actually using a respirator, He's in a wheelchair frequently, if not all the time. He required daily nursing attention, not quite round the clock, but pretty close. So he was in the highest risk category as far as health classifications go
in the federal prison system. He had some difficulties with a nurse there at at Coleman in Florida, where he threatened her, and after that happened, Bulger's health classification was oddly reduced. He suddenly was deemed that he was healthier, even though his age was advancing and nothing had changed.
And because that classification was reduced, that permitted the prison system to allow him to be moved, and rather than move him to a prison medical facility where he probably should have gone, they sent him Hazelton, West Virginia, to a prison called Misery Mountain that was riddled with violence and was in the middle actually of a of a of a real crisis with staffing because of budget cuts, and you know, there had been a couple of inmate
murders there, there was some guard attacks. So it was really a powder keg that Bulger was being sent to.
Why do you think, and you you speculate here or you theorize why he shouldn't have been sent to this prison specifically, and that there are prisons that somebody in his condition and somebody that's considered an informant would go to. Now, why would he be transferred to Hazelton? And what do you think about Hazelton and some of the inmates there in terms of why he wasn't they shouldn't have been sent there.
Well, you know, there's three prisons in the federal prison system where they send high risk inmates, especially informants. There's Tucson, There's Coleman, and there's Terre Haute, Indiana. It's known as the Triangle in the Bureau of Prisons. Misery Mountain is not one of those three prisons. Misery Mountain at Hazelton is somewhere where an informants should not be sent. It's
somewhere where informants will be targeted and killed. And you know when when they sent Bulger into that prison, they sent him into a prison that was filled with organized crime figures, including many from the Italian mafia, including many from Massachusetts, who were well versed in Whitey Bulger's lore. And to put him into that prison under those conditions, at his advanced age, with his health problems and knowing all that they know was was nothing short of a
catastrophic error, if not outright uh negligence and incompetence. And I think that you know, no matter what one person thinks of Whitey Bulger, you know, we live in a civilized society and we should not be intentionally putting prisoners into harm's way, and they should be the prison system should be taking steps to make sure that you know, the piece is kept and putting Bulger into that situation was not in line with those ideals.
And in October twenty ninth, twenty and eighteen, you chronicle what happened, and we will just leave it at that for people to discover all the details. And I know some people are clamoring. I've seen the just clamoring for those details. So needless to say, he was killed in prison, as we all know. October twenty ninth, twenty and eighteen. Did you succeed with this book in what you wanted to convey and what you wanted to demonstrate?
I think we did. You know, our goal with this book was, as I said, to tell the end of the story, you know, the final chapter in this twisted criminal saga that has really riveted you know, true crime officionados for decades, and certainly it's been a massive part of the media reporting here in Boston. For de k It's you know, forty years plus. So we really wanted to put the exclamation point to the end of this story.
We also wanted to dispel the myth in the notion that Whitey Bulger was this benevolent, good guy gangster, you know, a Robin Hood type figure. He was not that at all. And I think in the book people will get a good sense, a better sense than ever before, of what type of a person Bulger really was because you know, we have some of the most insightful letters that anyone's ever seen that reveal his character and it's right from
his own words, and that's really why I think. You know, this book gets to the heart of the matter like like none other before it.
And you also have included some fantastic, fantastic photos as well that the audience will get to see. Is the reader will get to see credible?
Yeah, there's never before. You know, the last known pictures of Whitey Bulger they were taken in prison, and we have those in the books, So I think people really like to see that.
Absolutely. I want to thank you very much, Dave Wedge an incredible interview Hunting Whitey, the inside story of the capture and killing of America's most wanted crime boss. I know people will go to Amazon, and I know this will be an audiobook as well. Is there a website or a Facebook page that people might take a look at this.
Yeah, I mean people can go to the HarperCollins website and just do a search for the book Hunting Whitey, and they can get more information. They ere they can track Casey and I down on Facebook just by our names, and we try to respond to everybody that reaches out.
It's been fantastic speaking with you, Dave Wedge, thank you very much for this interview. Hunting Whitey, The inside story of the capture and killing of America's most wanted crime boss. Incredible book. Thank you very much, Thank you. I have a great evening.
Thank you you two.
Good night, True