Matthew Cox | Inside True Crime Podcast - Whitey Bulger's Secret Confession to the FBI

Episode Date: September 29, 2026

Journalist Bob Ward reveals the untold story of Whitey Bulger’s years on the run, his secret conversations with an FBI agent, and the investigation that finally brought him to justice.⁣ ⁣ Bob'...s links - ⁣ Check out Bob's book here - https://a.co/d/07hBZ5qE⁣ https://www.linkedin.com/in/bobward3/⁣ ⁣ Get10% sitewide for a limited time. Just visit https://GhostBed.com/cox and use code COX at checkout. ⁣ ⁣ Do you want to be a guest? Fill out the form https://www.insidetruecrimepodcast.com/apply-to-be-a-guest⁣ ⁣ Shop my merch: https://www.etsy.com/shop/MatthewCoxCollection⁣ ⁣ Send me an email here: insidetruecrime@gmail.com⁣ ⁣ Do you extra clips and behind the scenes content?⁣ Subscribe to my Patreon: https://patreon.com/InsideTrueCrime ⁣ ⁣ Check out my Dark Docs YouTube channel here -⁣ https://www.youtube.com/@DarkDocsMatthewCox⁣ ⁣ Follow me on all socials!⁣ Instagram: https://www.instagram.com/insidetruecrime/⁣ TikTok: https://www.tiktok.com/@matthewcoxtruecrime⁣ ⁣ ⁣ Do you want a custom painting done by me? Check out my Etsy Store: https://www.etsy.com/shop/coxpopart⁣ ⁣ Listen to my True Crime Podcasts anywhere: https://anchor.fm/mattcox ⁣ ⁣ Check out my true crime books! ⁣ Shark in the Housing Pool: https://www.amazon.com/dp/B0851KBYCF⁣ Bent: https://www.amazon.com/dp/B0BV4GC7TM⁣ It's Insanity: https://www.amazon.com/dp/B08KFYXKK8⁣ Devil Exposed: https://www.amazon.com/dp/B08TH1WT5G⁣ Devil Exposed (The Abridgment): https://www.amazon.com/dp/1070682438⁣ The Program: https://www.amazon.com/dp/B0858W4G3K⁣ Bailout: https://www.barnesandnoble.com/w/bailout-matthew-cox/1142275402⁣ Dude, Where's My Hand-Grenade?: https://www.amazon.com/dp/B0BXNFHBDF/ref=tmm_pap_swatch_0?_encoding=UTF8&qid=1678623676&sr=1-1⁣ ⁣ Checkout my disturbingly twisted satiric novel!⁣ Stranger Danger: https://www.amazon.com/dp/B0BSWQP3WX⁣ ⁣ If you would like to support me directly, I accept donations here:⁣ Paypal: https://www.paypal.me/MattCox69⁣ Cashapp: $coxcon69 Learn more about your ad choices. Visit megaphone.fm/adchoices

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Starting point is 00:01:27 This family is on the brink of civil war. Mopland, the hit original series is now streaming on Paramount Plus. We are the Harrogans. Don't know the ant and Google us. From the underworld of Guy Ritchie. Do you want to step up the ladder? I won't call him dead. Starring Tom Hardy, Pierce Brosnan, and Helen Mirren.
Starting point is 00:01:47 Do I have to do everything myself? You want to want! I'll give you a... Blad, new season is now streaming on Paramount Plus. Whitey Bulger is a legend up in Boston. Rich Tien, the FBI age. why he opened up to him about his fugitive life. He reached out to me a few years ago and he said,
Starting point is 00:02:05 I know there are stories out there about his fugitive life, how he got caught, but I don't think that the story has been fully told, and will you help me tell that stories? I've been a reporter since 1983, and over that time, I've been covering some of the biggest crime stories in New England that have taken place over the last 30 years.
Starting point is 00:02:25 I just finished covering. Actually, finished is probably a loose word. I have been covering the Lindsay Clancy trial. I was in there every single day. I covered Whitey Bulger. I covered his fugitive years. I covered his trial. I covered the Boston Marathon bombing.
Starting point is 00:02:41 I covered Joe Harzaniath, the person who was convicted in that case. I covered his trial as well. So I've been up in Boston for a long time. Crime is basically my beat there. And I've covered some, like I say, some of the biggest stories that have hit there. And those are just the ones I think people in this audience would be familiar with. And you just finished this book? Or when did this get finished?
Starting point is 00:03:02 We published this book face-to-face with Whitey Bulger in April and working on it for a couple of years. Okay. How did the book come about? Rich Tien, the FBI agent, reached out to me because he felt the true story of what happened in Bulger's fugitive years hadn't been out there yet. But also, Rich wanted to get across that he debriefed Whitey Bulger for about five or six hours on board a Department of Justice private jet. And that debrief took place and he's flying back from L.A. to Boston and Whitey opened up to him about his fugitive life. And that's all detailed in this book. Whitey Bulger is a legend up in Boston. He was a gangster and rose to the top, Mob Boston, South Boston, and was an FBI most wanted fugitive for about 16 years. So it was a fascinating story that I covered all through the mid-90s going forward until his capture in 2011.
Starting point is 00:03:58 And I got to meet Rich Tien, who is the FBI supervisory agent, who headed up the Bulger Fugitive Task Force from 2006 forward. And Rich's experience, he reached out to me a few years ago, and he said, you know, I know there's stories out there about his fugitive life, how he got caught. But I don't think that the story has been fully told. And will you help me tell that story? So that's kind of how that's the background with this. Okay. So I have a quick question. Can you talk a little bit about Bulger's, you know, earlier life, like who he was.
Starting point is 00:04:36 But on top of that, the other thing I was wondering is, you know, like John Gotti was famous when he was running the mob. Right. You know, was Bulger famous? Like, if you were an average person, did you, like, if you were walking around New York, you'd recognize John Gotti. He was on this TV all the time. He was on, would you have recognized Bulger or was he kind of behind the scenes? Whitey Bulger was not like John Gotti or any of. of the well-known mobsters that we hear about in American history. He was a local guy in South Boston.
Starting point is 00:05:06 People in South East definitely knew who he was, but the average person could walk right past him at any time and have no idea who they were dealing with. And that's one of the reasons, one of the ways that I think that Whitey Bulger succeeded for so long, because Whitey Bulger was a ghost in a lot of ways. He was a ghost when he was running the streets in Southie, and he was a ghost when he was a fugitive. He was not flamboyant. We know that when he was a fugitive, he was holed up in a run controlled apartment out in Santa Monica. He did not have a posse of guys that were helping him stay hidden. He did not, he had plenty of weapons. He had plenty of cash, but it was just Whitey Bulger and his girlfriend in an apartment out in Santa Monica. He wasn't flashy. He wasn't throwing money
Starting point is 00:05:50 around. He didn't wear fancy clothes. He didn't have expensive cars. But he was just as ruthless as any of other well-known families that you hear about in New York or Chicago or wherever else. How did he kind of get to that position where he was running things? Yeah, Whitey, you know, he told Rich on the plane, and as you look back on Whitey's life, he kind of lived by his intellect. He felt like he was smarter than everyone else, and he kind of was. So he grew up in the projects of South Boston. He got arrested for the first time. He was about 14 years old. He goes into the Air Force. He has problems in there. And when he gets out of the Air Force, he comes back.
Starting point is 00:06:30 He gets involved with a crew and they're doing bank robberies and things. He ends up getting a stint in the Fed, federal penitentiary. He was at Alcatraz and Leavenworth. He was in Atlanta. It's a great photo of him in Alcatraz, by the way. There is in there. Yeah. Yeah.
Starting point is 00:06:45 I haven't seen his cell. I haven't gone to Alcatrash yet. You've never been to Alcatraz. I need to get out there. I need to go there because he's one of the featured guys. You can go see the cell that he was in. So he's, you know, he does his time in the Fed. And then when he gets out in about 65, he comes back.
Starting point is 00:07:00 And it didn't take long before. He just gets involved with the street gang stuff that's going on in Boston at the time. There's a war that took place among the Irish gangs. At the same time, the Italian mafia is operating freely up in New England as well. And so he has his rise. He gets involved in that life. He's involved in murders. He also allies himself with another guy from the projects, John Connolly, who
Starting point is 00:07:27 was an FBI agent that eventually was corrupted into their gang. He was able to parlay all of that and the information he was getting from the FBI to not only get rid of his Italian counterparts as the competition by beating information in the FBI leading to their downfall, but he also knows who's operating against him on the streets. And that allows him to continue his rise. And for a period of time, he and his partner, Stephen the Rifleman Flemmy, were the most powerful gangsters up in Boston. So did he had like an actual crew? And how many people?
Starting point is 00:08:04 He did. You know, it wasn't a huge crew. It was kind of like this confederation of guys. He had some strong people that he had with. It was Whitey and Stephen Flemmy had Kevin Weeks' enforcer. He had a hitman, John Monterano. They were kind of the core. And then he would have other people as well who were working, you know, making money.
Starting point is 00:08:23 on the streets, you know, all the different ways mobsters make money from loan sharking to drug dealing, all those sorts of things. You heard of Shea Red? Yeah, Red Shea. Red She said, right. And he kind of got involved, too. He was, I think he was paying Whitey tribute. And that's kind of how he was, he was sucked into that because he had to, he had to pay to
Starting point is 00:08:43 stay in business. What are they called it kicking up or something like that? Yeah, kickbacks. He had a, yes, they were skimming him and he paid and eventually he got caught, he got caught. Whitey didn't get caught. Did Fleming, did he know Fleming from like, you know, childhood or anything? I mean, he, I think, because in. Yeah, it's interesting.
Starting point is 00:09:00 Flemy was, you know, they were both, you know, they weren't, they were both running the streets, but they weren't with, Flemy was kind of, Flemy's Italian. So Flemy kind of had his hand in both camps, but eventually he aligned himself over with Whitey. Does that make sense? Yeah. So it isn't like a strict thing like the patriarch is into England or any of the families that you have in New York. but he was just as, you know, tight-fisted and ran, you know, if you're going to be in business, if you're going to be dealing drugs, if you're going to be doing anything, you know, card games,
Starting point is 00:09:31 anything, you've got to pay, you got to pay, you got to pay Whitey. Right. And that's just the way. What if you don't pay? You're going to, you're going to wish you paid. You're going to wish you paid. What about Connolly? How does he know Connolly?
Starting point is 00:09:44 Well, they knew each other from the, from South Boston. And they were aware of each other. Connolly, the Bulge family was a fairly well-known family back in the day, just because there were six kids, mom and dad, and the other brothers and sisters did not follow this path. Right. So they were, you know, they were, they were, they were quote, quote, a good family. John Connolly, also from Southie, he goes into the FBI. And this is in the era in the 60s when the informant program is going on, the top echelon informant program, H. Paul Rico, head of John Connolly, and they were prized on, there was a movement to bring down the Italian mob. And the way to do that
Starting point is 00:10:28 is to develop these confidential informants. And John Connolly developed Stephen Flemmy first as an informant, and then slowly brought in Whitey Bulger in the mid-1970s. And he had other informants, too, on the streets. And that helped John Connolly's rise to power as the Enjulo family in Boston was taken down by a lot of information from Whitey and his crew, that raised John Connolly's profile. And John Connolly eventually was convicted for his role in all this. He was almost like an extension of the mob of Whitey Bulger's mob over time. So it was just a corrupt situation that was taking place. And Connolly was reaping the benefits along with his supervisor, John Morris, by this, you know, deal with the devil, if you will, getting this information off the streets,
Starting point is 00:11:19 it turned into a two-way street where they were also, he was also giving information to Bulger and his crew, not just taking information. And that's what ended up getting John Connolly in big trouble. You know, there have been a lot of FBI informant kind of, you know, cases out there where they get too friendly, they'd give them too much. They start to think they're, they're buddies. Right. And I understand from the FBI's perspective, or not just FBI, it could be anybody, it could be Secret Service, FBI, you know, Homeland Security, whatever, that you want this guy to think we're friends, right? You want him to do his best for his buddy. But the FBI needs to realize like, hey, this is just an act. This guy's a criminal. We're not friends. But sometimes it goes over, like, what is it? Was it Scarpa? What was it Scarpa that had given the agent was giving him information? on witnesses and he's murdering witnesses, you know?
Starting point is 00:12:14 And so, one, I'm wondering if, because I've heard that that was one of the issues with Connolly, was it gave information on some girl that ends up getting killed. And the second thing is that I'd watched a documentary where the whole documentary was set up. It almost seemed like it was as a result of Whitey's lawyers or something. And they were trying to say, like, Whitey never gave him any information that Conno. is getting the, and the same thing with the black mask does the same thing. He's actually getting information from other informants to make it look like Whitey's giving it to him to protect him when in fact, Whitey's not giving him anything.
Starting point is 00:12:54 Whitey Bulger to the very end said, I'm not a rat. Right. I was not an informant. He told Rich that on the plane. It was one of the first things he said. I'm not an informant. I'm not a rat. Right.
Starting point is 00:13:04 And he was killed for that. Whitey was murdered in prison because these other mobsters said, we don't like rats. And that's why Whitey Bulger was killed. Right. But Whitey maintained that to the very end. I asked Rich that. Rich Tien, who's the FBI agent, whose story we tell him the book, you know, Rich has gone through the whole Whitey Bulger file, and the Whitey Bulger file is still sealed with the FBI. So there's no real public access to that. Even though Whitey is dead, he's been adjudicated, they're in the process of unsealing it, but it's taking forever. Yeah, who are you protecting? Why is it sealed at this point? I don't know. So I asked
Starting point is 00:13:35 Rich about that, and he said, if you look at Steve and the Rifleman Flemmy's file, And you look at Whitey's file. Everything that's in Stevens' file is also in Whitey's file, word for word. That file was opened on Whitey Bulger, possibly without Whitey even knowing there was a file. But it helped John Connolly continue to meet with Whitey Bulger. He couldn't just, he was meeting Whitey Bulger frequently. Yeah, you can't just hang out with a guy. You just can't hang out with mobsters.
Starting point is 00:14:06 But if you have a file, you can. Right. And I think that was a vehicle for him to be able to do that. working him as an informant. I went to dinner with him. Of course I went to dinner with him. He's my informant. He's, we're talking about the mob. We're talking about the Italians. Exactly. And they were paying. They were paying Connolly. They were paying his supervisor, John Morris, who testified at the trial against Whitey Bulger. They were paying these guys. But in Whitey's mind. Who's paying? Whitey's flying. Right. They're paying for information. Whitey says that on the plane to Rich.
Starting point is 00:14:32 I didn't, you know, I was paying for information. I wasn't giving information. I was paying, you know, to get information from the feds what was going on. It's kind of a big no-no, too. Yeah. That's kind of a- kind of frowned upon in the FBI. Exactly. So that's, you know, it was that,
Starting point is 00:14:49 it really is this unholy alliance. And it looks like Connolly was just as much a partner as Flemmy and Bulger. I don't think, I don't think there's any question that Stephen Flemmy and Whitey Bulger could have stayed in business as long as they were without that arrangement, even more so than Whitey's brother, who was the president of the state senate at the time. Right.
Starting point is 00:15:09 But it certainly would help, you know, if anybody was thinking about crossing Whitey Bulger, your brother is who? Yeah. It might give you a pause. But I think that the active ingredient here is John Connolly. So they're in Boston. He's running a crew. Like, how does it start to go bad or go wrong?
Starting point is 00:15:30 Like, well, one, Connolly, what about the, at some point he gives or Connolly gives him information or something. And on the on on a, does he end up killing? There's a there's a number of things that started happening that led to the demise of Whitey Bulger's rule in the streets. And. Thank you for clearing Mac. Yeah.
Starting point is 00:15:51 Eventually John Connolly retired. He was no longer an FBI agent and Whitey was still out there on the streets. So that was a problem. I thought he was still an FBI agent when he took off. No. John Connolly was retired and he was working for Boston Edison at the time. He was running security for Boston Edison. and he still had
Starting point is 00:16:08 he still had information coming in still had friends with the FBI and he knew that the federal indictments were coming and that's how Whitey decided that's why Whitey decided to take off Stephen Flemmy hung around Whitey Bulger took off but leading up to that
Starting point is 00:16:24 the downfall of Whitey Bulger started with a couple of murders involving World High Lie the Roger Wheeler hit in Tulsa and then the John Callahan hit down here in Florida. Those things...
Starting point is 00:16:39 So what was... They were the... They were trying to... They were trying to eat... John Callahan was, for a time, was involved with World High Lie. And he was giving Flemy and Bulger a cut of the profits. Is that even still a thing?
Starting point is 00:16:55 Is Highlie even still a thing? Insurance isn't a one-size-fits-all. And shopping for it shouldn't feel like squeezing into something that just doesn't fit. That's why drivers, have enjoyed progressives name your price tool for years. With the name your price tool, you tell them what you want to pay, and they show you options that fit your budget.
Starting point is 00:17:16 Enough hunting for discounts, trying to calculate rates, and tinkering with coverages. Maybe you're picking out your very first policy. Or maybe you're just looking for something that works better for you and your family. Either way, they make it simple for you to see your options. No guesswork, no surprises. Ready to see how easy and fun shopping for car insurance can be, visit progressive.com and give the name your price tool a try. Take the stress out of shopping and find coverage that fits your life.
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Starting point is 00:18:24 What does the sunny getaway with Air Canada sound like? Sunny Jamaica moves to its own rhythm. Rio comes alive, long after the sun goes down. Philippines slows everything down. And just when you think you've heard it all,
Starting point is 00:18:43 there's sunny Lima. However you imagine your sunny escape, Air Canada can take you there. Book hot fairs and vacation packages today. Nice travels. Oh, not anymore. Back then it was. So they were trying to turn it into like this national sport or something.
Starting point is 00:18:59 Right, exactly. But the mob was involved with it. So Callahan, who was on the periphery of the Bulger crew, is a business person, not as a gangster or anything. He was mostly legit, but he was friendly, and he liked the lifestyle. He kind of admired what was going on. But he wanted some protection against the Italian mob, so he's giving the Bulger crew some money. Callahan gets ousted, and this new guy, Roger Wheeler, becomes the president of World Highlie. And then Roger Wheeler gets out.
Starting point is 00:19:30 But the crew thinks he's going to, he's going to spill the beans on this whole arrangement. He's going to look at, he's, he's looking at the books. He's going to spill the beans on this. Roger Wheeler has to die. So that was one of the big hits. And it wasn't a, it was a guy, it was a legitimate businessman from another part of the country. It wasn't a Boston guy. It wasn't a gangster.
Starting point is 00:19:52 So he's taken out. John Callahan now. They shoot him in the parking lot. In the parking lot at his car, right? They just walk right up to him. John Monterano. the hitman for Whitey Bulger's mob walks right up to him and shoots him right in the head. John Callahan is still alive, and there was a fear among Bulger's crew that he was going to say something.
Starting point is 00:20:13 Callahan and Materano were friends, but Bulger put out the hit on Callahan down here in Florida at the time where he was, and John Moderano went to go pick him up at the airport and instead murdered him, and he was found in the trunk of a car. those things kind of move the needle on Whitey Bulger. And those things, he became more notorious. Like you asked me before about was he flashy like a John Gotti? No, he wasn't. But here, this was different. The tide started turning away.
Starting point is 00:20:44 People were getting murdered. And John Connolly was giving information out about movements of these targets. And everything started to coalesce and turn the tide against Bulger and Flammy. At that point, what is that when the FBI kind of that gets involved? It still takes a lot of time for this all to bubble up. But it kind of was the beginning of the end for Whitey. But it took years for it to finally, you know, the things finally start happening. The Boston Globe did some great work exposing, you know, Bulger's status as a confidential informant
Starting point is 00:21:20 and the relationship between the Bureau and how every other major mobster in Boston is getting busted except Whitey Bulger and Stephen Flemmy. How's that possible? Exactly. It's not possible. And that had been going on for a while. So that's what... And this is when he's still actively...
Starting point is 00:21:37 They come up with his article? And his brother is the president of the Massachusetts State Senate at the time. Yeah, it doesn't look good for him either. It doesn't look good. But he wouldn't talk about his brother. Right. He just said, I love my brother, whatever he's into. And he was, you know, Billy was still...
Starting point is 00:21:51 Billy Bulger the brother. He was still doing the annual Irish Day, St. Patrick's Day, breakfast in Southie. Everybody jokes about everything. Governor Weld is showing up with him and doing things. And, you know, I think he published a book in that period of time. I can't really remember if it was exactly in that period, but he put out a book, issued a published a book about his life. And his brother's a serial killing mobster. And nobody's talking about it until the globe finally started outing it. And then that's another thing is, you know, Whitey's world started shrinking. Well, I'm thinking, when does your guy get involved? He gets involved.
Starting point is 00:22:25 The events that have happened that we're talking about are some of them are in here. Okay. He gets involved in 2006, when he hits the road in 94. Okay. So why, how does that, why does he take off? Right, right. We can get into that. Okay.
Starting point is 00:22:43 Yeah, that makes sense. And then while he's gone, that's when his cohorts start telling people where the body, literally where the bodies are buried. Right. So everything. All right, let's do that. Yeah. Okay. The other thing I wanted to mention is, what's up with the Irish?
Starting point is 00:22:58 Didn't he give a bunch of money for guns? Yeah, gun running with the Valhalla. Yeah, very, and that's another one of the hits in this thing, John McIntyre hit. Yeah, he was, you know, Whitey wasn't just a one-size-fits-all gangster. He was involved in lots of things. And one of them was running guns to the IRA. And he arranged to have a shipment of weapons collected and then sent on this ship called the Valhalla out of Gloucester,
Starting point is 00:23:27 and it was seized by the Irish Army off the coast of Ireland. And there was an, I guess the IRA had, it was an informant on the IRA. It gets really murky, really fast. But actually spilled the beans on this whole thing. And it led to this guy, John McIntyre, who I guess wanted to tell the feds what was going on or whatever. And when it got back to Bulger and Stevie, they had him killed.
Starting point is 00:23:53 a lot of people getting killed. A lot of people. If you crossed Whitey Bulger, if you crossed Whitey and you threatened to talk to the FBI or cut any kind of a deal to save yourself, you were as good as dead. You should probably move to Palm Beach. You end up in a pit in the quarries,
Starting point is 00:24:12 and the salt marshes and the Pound's at River and just outside of Boston, that's what happened to you. What kind of money is this guy? People are kicking up to him. and I mean, what are these rackets that he's running to make money? Is he, which is he extorting like the local bodegas? Or is he, because that always bothers me, but the guys that idolize the Italians, mob.
Starting point is 00:24:38 And I'm like, you understand that they extort people. Like you, you saved all your money to open up a bodega. And now this guy's coming in and saying, you got to give me $400 a week. And it's like, what are you talking about? Like, I've worked 10 years to save money to start this store. I got to pay you $1,600 a month to stay in business. Yeah, we'll just start throwing shit through your windows or burn your whole place down. And then people around the neighborhood are like, he's a great guy.
Starting point is 00:25:00 Why? Because he bought you some chickens or some turkeys for Thanksgiving. That's exactly it. That's exactly how Whitey made his money. When I sat through that trial, let me back up just a little bit. There was a myth that Whitey Bulger was, in South Eastee, there was a myth that Whitey Bulger was keeping the drugs out of South Boston. When, in fact, when I sat through that trial, he was making.
Starting point is 00:25:20 money hand over fare on you name it he was making money and he was making millions of dollars and he was also shaking down anyone that that he thought he could you know granted these you know a lot of these people are you know running rackets or something and that's where he's trying to get his money from but honestly if he thought he could get 10 bucks out of you he would get 10 bucks out of you and that's just the way it is it was fear intimidation and you're right there were these you know there There are people, these apologists, who thought he's a bad guy, but he's our bad guy. He's on our side. Whitey Bulger was only on his own side. And he made millions. I saw one estimate of up to $30 million that he had. They only found $822,000 in cash in Los Angeles in Santa Monica in
Starting point is 00:26:06 the hide in his apartment. Where's the rest of his money? He didn't spend it the entire, he did not spend those millions of dollars in 16 years because he lived, he lived, frugally. They found him stretching his socks over bottles of bleach in his apartment because he was buying cheap-o socks and he was trying to stretch them to, and we have a picture of it in the book, trying to stretch it so it'd fit his feet. Right. That's what he did. Yeah. He would cross the border down into Mexico to get heart medication. He would just kind of walk right across the border to get medication. So he was not living large at all. In fact, you know, you did Fed Time. You'd know better than me, But I would just say that in a sense, granted he wasn't behind the four walls of federal prison,
Starting point is 00:26:51 but he was living like a prisoner in an apartment in Santa Monica with his girlfriend, but he wasn't really living. He was looking over his shoulder the entire time. So how does it all kind of start to go down or fall apart at when the FBI gets involved? That's a, it's a long story. You're not going to believe this. It is a long story. We have the time. And it's all included in my book.
Starting point is 00:27:21 Well, Whitey, when he first took off, what happened was when the warrants went out, when what I understand, the state police were, they were tasked with getting Stephen Fleming. FBI was tasked with getting Whitey Bulger. So the warrants come out. Stephen Flemmy's brought in right away. Stephen Flemmy didn't take off. He was local. And he knew that this was coming. out. Right. And he didn't, he was warned just like Whitey was, and he thought that we'll get through
Starting point is 00:27:48 this. And why wouldn't he think that? Because every other time they got in trouble, something was arranged and they were fine. He didn't see the danger in this. Whitey Bulger, on the other hand, who had been planning for this, had been working on fake IDs for a good 10 years before this, and had a plan, decided that because I spent all that time in the Fed prison system and got out in 65, I'm never going back to prison. He worked on, he called it his little project with him and Kevin Weeks, coming up with the fake ID that he would need. It was really only one ID.
Starting point is 00:28:22 He had other, there's a whole thing about IDs that he had. He knew how important they were. But really there was one really good ID that he had. And he disappeared with it. He was out with one girlfriend, Teresa Stanley, and they were out traveling around the country. He kind of knew things were going to turn bad. And as he's approaching Boston coming home to Boston, he hears on the radio that the indictments are up and they're looking for him, he turned around
Starting point is 00:28:44 and took off. He ends up in Long Island, New York, where Kevin Weeks' cousin lives, and that was kind of where he hid out for a little while with Teresa Stanley. Then they started traveling. They ended up down in Grand Isle, Louisiana for a while, where they had a ton of cash, and they're thrown it around with a local family there, living as under the new ID, buying this family in refrigerators and paying for medical bills, this, that, and the other thing. And then before he got there, Teresa Stanley wanted to go home, she got homesick. So he dropped her off, picked up Catherine, Greg. Another girlfriend.
Starting point is 00:29:25 Another girlfriend. That's the one he ends up arrested with. Right. So real quick, the ID that he gets, what is this ID? It's a real guy. Yeah, it's a real person. His name is Thomas Baxter, lived in Massachusetts. And I don't know how he settled.
Starting point is 00:29:40 this guy but he got his birth certificate and made sure he got a driver's license in that name and renewed it every four years made sure had it on a calendar and just worked on that and once he was no longer james bulger he became tom baxter and he bought a couple of grand marquis but you're saying baxter is a real person was a real person right was like hey was he deceased or he also got the same driver's license i think he was dead at the time okay i'd have to go back and look but i think You know, that detail I just don't remember off the top of my head. But yeah, he was a real person. Okay.
Starting point is 00:30:13 And that was kind of his M.O was get a real person's information so he could start making. The only problem is that real person's still around, they figure it out. Like, or there's conflicting, you know, they get a DUI and you're driving around on a driver's license that, you know, has a, has been suspended for a DUI that two states over that you don't know about. You know, that's the problem with with those using a real person's ID or whatever, they get arrested or they, they die. and suddenly there's a death or there's a death certificate out there and you're trying to rent a room and they pull your credit and says this person's deceased because it'll show up on your credit so that's why i'm wondering like how did he you know figure that out yeah that's what he did i do remember rich telling me that um he was on there was one guy that bulger maybe it was baxter was using his id and every time
Starting point is 00:31:00 he was trying to leave the country they would get a call and they'd have to go down and make sure it wasn't whitey bulger so i don't remember if that was a tom baxter idea one of the other ideas IDs, but that did happen. Yeah. So anyway, he brings Teresa back, takes off with Catherine, and Teresa knows what the fake ID is. And she tells it to another street guy who's an informant, who's trying to make a name for himself within the bureau, tells him about the ID. He kind of hones in on Teresa when she's dropped off and kind of gets close to her. So she gives that information to him.
Starting point is 00:31:36 He tells it to his handler. And then Kevin Weeks back up here in Boston warns Whitey that the ID, Kevin knew about the ID because he helped him with it. On an arranged phone call, got the information to Whitey and said, you can't use that ID anymore. That forced Whitey to run and head out to eventually Santa Monica. And in between before he took off, he worked on getting more IDs. I went to his crew because they hadn't turned on him yet, trying to get other IDs to him that he could use. And eventually the smartest thing I think Whitey Bulger did was once he got what he felt that he needed, he and Kath and Greg got on a train and headed out to California.
Starting point is 00:32:16 And nobody back home, he didn't tell his old crew where he was going because he didn't really know where he was going. He just got on a train and went out west. He didn't really understand where he was going to hold up. So once everything went bad for him and people started turning on him, they did not know exactly where he was. and that protected him for a long time. Because once he got out to California, he worked on new IDs out there that nobody back here would know about.
Starting point is 00:32:43 Now, we don't know if his family knew. We do know about the IDs or where he was or any of that. There's no evidence that we know of, but we do know that what he was in touch with people in South Boston during his fugitive years, and some people actually saw him. He came back. He talked about it to Rich on the plane that at one point he did come back to Boston.
Starting point is 00:33:02 He was looking for somebody. And he wanted to kill him. And he was back here. And since the book has come out, we've talked to people, said we knew that was him. But we didn't want to say anything. He's still trying to take people out. Just there's one person. He claimed, Rich asked him when you were fugitive, did you ever come back to Boston?
Starting point is 00:33:21 Did you go anywhere else? And he said, I did. He said, I was quote unquote, armed to the teeth. I wore a disguise. And I went back looking to settle an old score. And he would not talk about who he was looking for. why do he consistently through this plane ride refused to talk about anybody who was still alive?
Starting point is 00:33:39 If you were dead, he would talk about you. If you're still alive, he would say, if it was Kevin Weeks, he would say, go ask Kevin. Right. I'm not telling you. So I think we have an idea who he might have been looking for, but I don't know and he wouldn't say. That's the problem in heat.
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Starting point is 00:35:43 However you imagine your sunny escape, Air Canada can take you there. Book hot fares and vacation packages today. Nice travels. Guy could have got away and he just couldn't let this old grudge. Couldn't do it. See some of these guys? You see the movie Heat? Yeah.
Starting point is 00:35:59 I mean, obviously, it's fiction. Yeah. I love that movie. But that's the thing. Yeah, he was very thin-skinned, very intelligent, but he was thin-skinned, and he wanted to settle an old squirt. They found in his apartment, you know, his book collection. And it was all about books written about Boston mobsters. And in the margins of the book, he's got things underlined.
Starting point is 00:36:20 This is BS, F-U, blah, blah, blah. You know, he had that. Angry, angry bulger. And then he also had a manuscript he was trying to write. He was trying to write his own life story. He didn't get very far, but he had a legal pad and he starts writing out his story. So one of the things Rich and I talk about is it's kind of amazing. This guy who didn't want to be a rat tells Rich Tien on a plane his life story after first getting arrested before even talking to a lawyer.
Starting point is 00:36:45 And, you know, we kind of think that maybe he felt, I'm done. He's got to know he's done. It's done. He knows he's never. He fell for the ruse in Santa Monica. Isn't that the oldest ruse in the book? Well, but it really happens. If you think you're 100% in the clear, if the leasing agent says, hey, we got an issue,
Starting point is 00:37:04 yeah, what's up? You know, how many times is somebody knocked on his door and they're like, hey, we're checking the plumbing or we're spraying for pest decks? And it's probably, you know, for pests and they've come in and spray it and left and nothing ever happens. So there's lots of interactions. Yeah. You know, where you have, if you have, the more you have, the more emboldened you become and start believing you're untouchable. And he had to think he was untouchable. Plus, he's got a fake ID.
Starting point is 00:37:29 I'm living in this place. I got this chick. I got a bunch of money. Got a bunch of guns. Like, these guys are never. I've been on America's Most Wanted. Like, they're never going to catch me. However, the PSA had just come out and he was aware of it.
Starting point is 00:37:42 And he told Catherine, I think this is it. So you think that when the superintendent or whoever was a building manager calls him and said somebody broke in your storage locker, can you come down and check this out? You think that a light would have gone off. What's he going to do? Not go down there. No, fuck. That's it. Tell them to come get me. I'm going to hold up. I'm done. I'm the old whitey. I think the old white he would have never fallen for it.
Starting point is 00:38:06 That's all I'm saying. And I think he was, I think there was a side of him that was tired, was ready to go. He actually talked about his own what would happen if he died out in the road, as a fugitive. If he died, what he would have done. And he talked about it on the plane. So I think it was on his mind. The fact that he's writing about it in his manuscript, the fact that he's writing things in the margins, it got to the point where he just wanted to tell the story.
Starting point is 00:38:28 He never testified at his own trial. He was given the opportunity. instead of testifying and taking the stand and bringing down everybody in Boston, which is what we were all in the media waiting for. We wanted to hear that it wasn't just John Connolly and John Morris. We wanted to hear more names. And instead, he stood up and he said, this trial's a sham. And he sat down and took his punishment.
Starting point is 00:38:48 And that was the end of it. That's the end of Whitey Bulger. He wrote some letters, too, when he was in captivity. There were some people that wrote to him and he wrote back. And you'd get little glimpses of the whole thing of what was on his mind. Well, wait a minute. Wait, he wrote when he was on the run? No, no, when he was in prison.
Starting point is 00:39:03 Okay. So let's go back to the, how do they find him? I mean, we talked about it earlier, but there was no camera then. How did they narrow down? Because this is what, 15, 16 years on the run? Yeah, he got a year 16 and a half is when he finally got caught. Did he ever leave the United States other than walking across the border? Other than walking across the border?
Starting point is 00:39:23 No, he did not. We thought there was a real feeling that he was abroad and was trying to get back to the United States, but couldn't because of 9-11. And that he, you know, whatever passport he might have been using was an old passport. It wouldn't be legit, obviously. It would be an old passport. He wouldn't be able to get a new one to get back or whatever. I don't think it would be hard for him.
Starting point is 00:39:42 If you can get a driver's license, you can get a passport. Right. Without a doubt. Right. It's very easy. He didn't do it. He did go before, just before he became a fugitive. One of the last things he did was he and Teresa went on like a little tour.
Starting point is 00:39:55 And they were in England. He was checking on a safe deposit boxes in Dublin and London. And then he came down here. There was one in Clearwater. There was one here. And he was visiting all safe deposit boxes, moving money around. He was doing that. And that's what he was doing when he found out he was indicted.
Starting point is 00:40:12 So he turned around and just stayed back out. So he's with Teresa. She thought she was just going on a road trip. She didn't realize this is the rest of my life. That's why she wanted to come back. She's lucky he didn't kill her. Yeah. And, you know, so what ended up happening was,
Starting point is 00:40:28 everything that they were trying to do to try to find Whitey didn't work. There were sightings of Whitey that were always months old. So we in the media would go out. We'd have almost every year there'd be an effort by the FBI to publicize it and there'd be a big banner. Where's Whitey? We had a map printed out of all the legitimate sightings. And I think there are about a dozen sightings of Whitey over the years. We're always wondering about the latest one.
Starting point is 00:40:53 Where's the most recent one? So it come to find out, you know, I don't. think they were ever close until this they finally got him i don't believe they were ever close to finding him there was no um there was no moment where if we were just an hour earlier we would have had him that sort of thing none of that ever happened he was he was gone but he was hiding in plain sight out in santa monica so in 2006 rich gets on the task force and rich had been a fugitive hunter in new haven connecticut and he was involved in a couple other top 10 investigations so he comes up to Boston. He's a Boston guy. They bring him up there and he's bringing them all together.
Starting point is 00:41:30 And there are different agencies involved. It's not just the FBI. Some people on there for the DEA, Department of Corrections, State Police. And they're trying to work together to formulate some kind of plan to get Whitey Bulger. And one of the plans that they tried to do was to go after Billy Bulger, Whitey's brother. And they were prepared. The idea was we should get him for harboring on a harboring charge because Billy got in trouble for the information to come out that he had lied to a grand jury or spoken to a grand jury about taking a phone call from Whitey at a lawyer's house and then when he was called before the grand jury wasn't truthful about it that led to these congressional a congressional hearing and around 2002 I think it was that harboring
Starting point is 00:42:15 not sure I'm not sure what the legal aspect of this way you know what I'm saying well he was he knew he was and he wasn't being honest or maybe lying to congress that doesn't that phone That phone call doesn't mean he knew. That just means I accepted a phone call. Right. They were working on something. I don't know what the evidence was. They were trying to do something.
Starting point is 00:42:31 They were trying to do something. And that's why it didn't. And what you bring up is why it didn't go forward. Yeah. So what happened was the people on the task force thought this is a solid plan. If we can go after Billy, who's kind of, you know, like a Irish cousin of Whitey, he's not going to let his brother take the fall. He's going to just come in out of the idea was that he would just commit.
Starting point is 00:42:53 out of the cold and say, you know, you're after me, not my brother. Yeah. It's over, okay, and drop the charges against him. Something will happen. We'll force Whitey to do something and might lead to his capture. But what ended up happening was the U.S. Attorney's Office in Washington told Boston, this is your call, it's a jump ball. We think it's kind of circumstantial, probably the things you're talking about.
Starting point is 00:43:18 We don't feel comfortable with it, but if you want to go forward, we'll support you. And the U.S. attorney at the time decided on the 11th hour not to do this, just as the statute of limitations was about to run out. But he did go up to the task force, which was meeting off site and spoke to them and said, we're not going to do this. Nice try, but we can't do this. We don't believe in it. We don't think it's a solid enough case. We're not going to do it. And almost blew up the task force because some of these people had been on it for, you know, 10 years and they were frustrated and thinking nobody wants to catch them.
Starting point is 00:43:49 We can't believe this. And that Rich was there, my Rich Tien, the co-author here, he was there for that. And he witnessed that firsthand. And there was a big fallout. A lot of people left. They just, I don't want to do this anymore. And they regrouped. And over time, they decided to focus on not Whitey, but on Catherine Gregg.
Starting point is 00:44:09 So all the efforts, every time we in the media would do a story about where's whitey, it was always where's whitey, never where's Catherine. Right. There might be a photograph, an old photograph of Catherine Gregg, but not a, not a, not anything in depth. So what ended up happening was they developed some plans. They found some photos of Catherine Gregg when she had plastic surgery done and some dental work done that were really good 3D images, high, you know, high resolution images,
Starting point is 00:44:37 I should say. And they use those images. Have you seen this woman? Exactly. And they have a picture of her. Nice picture of her, put her in the trades. Of her teeth. Exactly.
Starting point is 00:44:46 Her whole face, though, looking this way, almost like a mugshot. Right. And in color. And they put those out there in trade magazines and for plastic surgeons and also dentists. And then they developed a public service announcement, TV ad, if you will, 30-second thing, that utilized that those images, plus some video of Whitey that was taken back when there was a surveillance of him, some video of him back from the 80s, I believe, old black and white stuff. And they made this very, you know, very jarring attention-grabbing. PSA, and they aired it in some of the markets that they suspected where he might be, one of them being LA.
Starting point is 00:45:24 And the coverage of that PSA, the news coverage, brought forward the tipster, who said that they, they were, they saw Catherine. They believe that it was this, this woman that they befriended over a stray cat, and whose name was Carol, was actually Catherine Gregg. And I think the tipster had seen Whitey, who was Charles Gasco, but he was kind of standoffish. And that's the tip that ended up being the tip that led to the ruse in the garage in Santa Monica that brought Whitey Bulger down. So that PSA aired. And then about two days later, Whitey Bulger's in custody after 16 years of knowing where he is or any close calls or anything. So they just go to the leasing agent.
Starting point is 00:46:19 And they just asked to call him and say, hey, look, your storage unit was broken into. Right. Exactly. They were set up in the basement. Right. There was also a $2 million reward on Whitey's head. So I got to mention that too, which was the highest reward at the time. There was a $2 million reward.
Starting point is 00:46:33 So they were serious about this. Rich is in Boston. He's taking tips that are coming in from the PSA. First one comes in about somebody a look-alike in Biloxi, Mississippi. It takes a little bit of time to run that down. Second one is the good tip. And Rich and his team here start trying to work on who's Charles and Carol Gasco. Who were they?
Starting point is 00:46:54 And you come to find out that they don't have a previous history. There's nothing. And that was the red flag. That he contacted the LA office of the FBI, Scott Garriola, who was a fugitive hunter out there. And he spoke to Scott and Scott said something like him on vacation. And Rich said, you've got to do me a solid man. You've got to come down here. You've got to do this.
Starting point is 00:47:15 So Scott marshaled the plan. And, you know, they set up down in the basement. They made the move on the building manager who calls Whitey Bulger and said, look, somebody still broke into your storage locker. There's a problem. Can you come down here and check it out? And Whitey gets in the elevator, comes down. And as soon as the elevator door opens, he's arrested.
Starting point is 00:47:35 And you knew it. You knew it was all over. Catherine was still up there. And they had to work on getting Catherine to. But inside that apartment in the hides that he hand cut himself, was $822,000 in cash and a lot of weapons. What do you mean to hide? He cut holes in the walls of his bathroom.
Starting point is 00:47:54 And he stuffed cash, $822,000 worth of cash into those holes along with weapons. He also had underneath his bed, he had a duffel bag with ammunition, more weapons. I think he had a live, I think he had a loaded gun on his nightstand. I mean, the guy was ready to go. It's almost, you know, and I was thinking about the Valhalla, the types of weapons he tried to send to the IRA, he had a similar stash, maybe not as large, but a similar stash with him up there in the apartment in Santa Monica. So he was ready.
Starting point is 00:48:24 If they were coming for him, if this was going to be a traditional, you know, SWAT team kind of operation, he wasn't going to go. Like, you know what I keep wanting to say is we have a guy that comes on. He's a retired FBI agent named Tom Simon. Mm-hmm. I keep wanting to say, you know, Tom Simon would have caught him. He's got all these cases where he would, he had caught these guys that had been on the run for 10 or 15 years. And like everybody just kind of gave up.
Starting point is 00:48:52 They're like, yeah, he's wanted, you know, if he gets picked up. But they're not looking for him. And he would find him. Like he would. Right. And they would give it to him because he was a new guy. Like a new, you know, he'd been there, whatever, weeks or months. And, you know, they'd say, you know, I was assigned this case.
Starting point is 00:49:04 What do you think I should do? And they would be like, a 15 year old. This is 15 year old. The guy went to Mexico. He's Mexican. He's gone. It's never going to get him. He's like, no, no.
Starting point is 00:49:13 And then he would. figure out a way to find the guy and actually get him. And it would fly in and the guy would actually fly in. Like he thought he's being contacted to be a part of a documentary because he was the, what was the, he's like tango dance. The tango king. Yeah.
Starting point is 00:49:27 Yeah. And so they were closing this, this dance hall and they were doing a documentary and he contacts the guy. And he actually figures out a way for that guy to kind of reach out to him. Because he knew, he knew he had a magazine. He found out that he had a magazine subscription. Didn't even know if he had the subscription.
Starting point is 00:49:44 but thought he probably does. And he'd know that he had written a letter into it like 10 years earlier. He's like maybe he still has a subscription. So he puts out a thing, finds out he does have it, writes him a letter. We're doing a documentary. But we'd love to have you. We understand that you won you were the tango queen king two years in a row. I'd love to.
Starting point is 00:50:05 And the guy actually flies himself in and he gets arrested at the airport. And then when they're driving to the FBI building, the guy says, listen, is there any way we can stop by the such and such ballroom to let them know I'm not going to be able to be interviewed for the documentary. Oh, my God, when a moron. Yeah, he's like, we're going to let him know. A moron. But there's, he's got a bunch of people that he tracked down or just made so miserable that
Starting point is 00:50:30 they turn themselves in or. Yeah. You know, they say that, you know, people, it's easy to become a fugitive. It's harder to stay a fugitive. Because people plan for the escape, but they don't plan for what happens after that. Yeah. And that's really the problem. Don't I know it?
Starting point is 00:50:45 Yeah. Whitey, though, was an exception because he did plan for it. He was gone forever. Yeah. I mean, that was, I remember when he got... Insurance isn't a one-size-fits-all. And shopping for it shouldn't feel like squeezing into something that just doesn't fit. That's why drivers have enjoyed progressives' name-your-price tool for years.
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Starting point is 00:52:43 We follow the money. Learn more at Bloomberg.com. I arrested one of my buddies came up to me and said, bro, they got your boy. And I went, who's that? And Whitey Bulger, I went, no. Like, at first of all, it's not my boy. I just know who he is. But I was like, are you seriously?
Starting point is 00:53:01 Yeah, he's like one of the longest running fugitives. It was 16 years. I was like, wow, that's crazy where they find him. And within a week or so, there was a bunch of programs on how they call him. Yeah. I always remember one of the ones was. I forget who they interviewed where they said they pulled the guns on them and they said, you know, get on the ground or get on your knees. And he said, I'm wearing white pants.
Starting point is 00:53:22 Fuck you. I'm not getting on my knees. There was an oil slick or something in the garage. Yeah, that's the way he was. He was badass right to the end, as long as he could. As long as he could. So they grab him and they bring him downtown, right? I'm assuming they bring him straight to the FBI headquarters.
Starting point is 00:53:41 Oh, they brought him to the courthouse. They brought him to the court house, right? And that's where Rich comes in and finds him and sees him for the first time and hold up, lockup before his initial appearance out in L.A. And he goes in and Rich described that when he got there, of course, the whole world's press seemed to be there. And they were all looking for something. And he gets led downstairs and he meets Whitey Bulger and explains to him who he is. And he said, Bulger just looks totally defeated. Catherine looked defeated, not defiant at all.
Starting point is 00:54:11 And Bulger understood why he was there. And he said, I'm going to be taking you back to Boston. And we'll see you after the proceedings are over. And then the arraignment happens down in, or the initial appearance, I should say, happens out in LA. And he waived his extradition rights. And the next morning, they're on a private government jet, added back to Boston with Rich. How old was he? I think he was 79 years old.
Starting point is 00:54:37 He's an old man. Yeah. Old man. And then on the, on the. plane that's when he what is he makes him offer or right so rich said to whitey bulger i want to talk to you i'd like to talk to you about what's happened and immediately whitey goes into let's make a deal and he said i'll tell you everything you want to know but i want immunity for her for kaffirn who was sitting at the front of the plane and rich just said listen um i'm not authorized to make a deal like
Starting point is 00:55:07 that, but I'll definitely take your concerns higher up, but I want to know if you will talk to me right now. And why did he agreed? Waved. He signed any paper he needed to sign and agreed to talk. And it's almost like he, Rich said it was almost like he was finally putting on a show. It was like his legacy. He wanted to speak. Now, Rich was there, along with another FBI agent, Phil Torsney, they were there to talk about the fugitive years. They specifically were not there to talk about the case. Because that was the open charge. And they wanted to know who was helping him, who in Boston was still, they knew where
Starting point is 00:55:46 he was supporting him. And they wanted to get those sorts of details. And why he talked about a lot of things? And sometimes he would stray into some of the old cases, but not in any kind of depth, not in any kind of detail. And he would only talk about people who were dead. He wouldn't talk about people who were still alive. Okay. And he breaks down exactly the whole thing, the IDs, the, you know.
Starting point is 00:56:11 Yeah. And so over the course of time, the story unfolds how white he lived his life. Where did he go? And how did he live his life? And that's where we find out that once, one of the interesting things is when he first gets to California, they get a hotel. And the next day, they wake up and to the sound of helicopters overhead. And they look outside the, window of the hotel and there's massive amounts of reporters, crowds, helicopters overhead, and he shuts the shades and he says, Catherine, they're here for us. We're done. And what is something completely different? What is it for? OJ.'s civil trial. Oh, this is a courthouse across the street from his hotel. Wow. Can you believe that? So he said, okay, fine. Then they snuck out of a door and got down to Santa Monica. They were going to go to Venice. He had traveled.
Starting point is 00:57:03 to Venice and he liked it there, but he just figured he couldn't really fit in as well as he could in a place like Santa Monica, which he also liked. He liked Santa Monica because there was there were a lot of older retired people. And he could just fit in. And he did. I mean, he's just an older white guy. People just walk by him on the streets. So I have a quite, I have a something I'll tell you real quick. When I was on the run, I went to Nashville, right? I had actually been caught in South Carolina in Columbia, South Carolina, and got out and handcuffed, brought downtown, convinced them. I don't know if you know anything about my story, but I convinced them that I hadn't done anything wrong. They had the wrong person. I had a fake ID and the whole
Starting point is 00:57:42 thing. And they, and I convinced them that the bank had made a mistake, you know, and they said, okay, we're going to look into it. And they, we did a police report and let me go. I then, of course, get all my stuff, grab some money and take off. I end up in, in Nashville, Tennessee. And I'm in Nashville and I keep going, I go to a Starbucks and I would go in every day for, let's say a week. And I hadn't been there long, maybe a week or so. And I go into the Starbucks one day. I remember walking in and there's this guy that almost looks homeless. We're both walking in at the same time. And he kind of walks in behind me. I'm standing in line in Starbucks. I'm waiting. And there's two cops that are over here. But I'm not, you know, this is back probably kind of before like social media. So it's like I'm, I'm in the newspaper, but I'm in, I'm in the Atlanta newspaper, and the Tampa News. This is not every. You're out of the area. Yeah, you could go online and look for people, but it's not like it's, there's
Starting point is 00:58:37 TikTok and everything. Right. So I'm sitting there. I see the two cops and I think, no big deal. Keep in mind too, I've had a nose job. I've had plastic surgery. I've had my teeth done. I've had my hair done.
Starting point is 00:58:47 I've had done everything. So I'm sitting there. And I remember a couple of college, there's like young girl college students who kind of glance over at me and they look and they stare at me. And they're like, they say something. And they're like, oh, my God. They keep staring. Then the two cops look at me.
Starting point is 00:59:04 And I'm sitting there going, holy shit. And then somebody else looks over at me. And I think, oh, oh, you fucking idiot. Like, for all you know, you're on, this is, they're still printing newspapers at this point. Yeah. Like, for all you know, you're on the fucking front page of the newspaper. You know what I'm saying? Like, what are you doing?
Starting point is 00:59:26 Like, you've, you've come in there. the same place every day, because I never worried before, right? I wasn't clearly, but I'd never been in this position. So I've now got six people in this Starbucks that's crowded in the morning, looking and looking and looking and looking and kind of glancing up. And I'm like, finally, and the cops are staring at me. And my first thought was, I take off right now. I will never get into my truck.
Starting point is 00:59:51 Like, I might be able to get into my vehicle. But I'm going to have to back up. And these guys are like, I'm not running over some cops. Like, I'm not doing it. And I was like, there's no fucking, you're done. You're done. And at that same time, one of the college students, she stands up, walks over to me, looks me right in the face and says, oh my God, I'm a huge fan.
Starting point is 01:00:15 Can I have your autograph? And the guy behind me says in an Australian accent, of course, love. I, you know, of course, you have a pen. Do you sure, I'll have no problem? I turn around and it's Keith Urban. The guy that walked by, I was staying in an area called Green Hills, which was right next to Music Row, which was a very nice. All these houses are multi-million dollar houses around me, you know, and I'm just like, I was like, I mean, I recognize him immediately. But I didn't, I recognized him when he started talking, I realized like, holy shit.
Starting point is 01:00:50 He had blue jeans that are torn, but I realize now like, yeah, they're $500 blue jeans that are torn. They're professionally torn. You know, and I just remember thinking, oh, my God, oh, my God. So, yeah, I was terrible. So that whole looking at the window, they're here for us. They're here for us. Right. I could totally see that.
Starting point is 01:01:06 Because you're already semi-paranoid. Right, right, right. Oh, my God. That's hilarious. So did you get your coffee? Oh, yeah, I stayed there. But, I mean, I was sitting there. It's the first time I ever, it's funny.
Starting point is 01:01:16 The first time I ever really felt like, like, like, this, like that, like, fuck, I'm like, I'm done. Like, even if I run right now, I'm not getting it. I'm not going to go anywhere. Where am I going to do? Right. Yeah, if you saw the area, like this is a nice, beautiful landscape, well-planned-out area. Like, I'm not out-running two cops. Right. I'm certainly not out-running radio. Right. Like, I'm done. Where are you going to go? Yeah, I'm not going to do that. So did it change your plan after that? Like, did you stop going to Starbucks or what did you do? What it did was, no, of course not. What it made me think is un-untouchable. Oh, wow. Because here's the problem is that, you know, being as high as I am on the, you know, sociopathic scale. You know what I'm saying? Like, I just be. became more emboldened thinking. Interesting. Even when you, for sure, the cops are looking right at you.
Starting point is 01:02:02 Like nothing. Like, oh, you're, you're stupid for thinking they're going to catch you. You're just that good. Wow. You'll never, they'll never catch me, coppers. So interesting. So stupid. Yeah. Well, why do you, why do you went through the same thing? The exact same thing. You also had another brush with the law. He tells a story about to Rich on the plane about how he stopped at one point to help somebody with a flat tire. and the cops came. And meanwhile, he's at the front working on the tire, and the cop eventually left.
Starting point is 01:02:32 And they asked him, they said, did you have a gun on you when that happened? He said, yes, I did. What would you have done? Would you have shot the cop if he asked for your ID? And he denied it. But what do you think he really would have done? It was a stretch of highway in a desert. I'm not even sure where this happened.
Starting point is 01:02:46 Right. But it's out in the middle of nowhere. And that's where he was. It would have just been him, the cop, and the two people in the car. Who knows what would have happened? Had he actually, like killed people himself. Oh yeah.
Starting point is 01:02:58 Okay. Oh yeah. He killed two women with his bare hands. He was shooting people in the back of the head with, he used an ice pick in another one. Because I know I saw, you know, I, it's funny with Black Mask. When the move, when the book came out, it was going around the compound. I was like a.
Starting point is 01:03:12 And, uh, and then when the movie came out, I saw the movie, but you just, you don't know. You don't know. They exaggerate things. No, he, he physically killed people. Right. He wasn't just ordering hits and some higher up. He was, he got his hands dirty and everything. thing that he did right he didn't just rely on other people to do things for him he wasn't this
Starting point is 01:03:30 you know spengali kind of guy or you know mob boss just sits back and people pay him tribute that's not what it was at all yeah then i wonder if he would have uh the cop asked for his id he would have had a fake ID but what if the cop recognized him you know what if he gave him like that yeah because to me i'd give him the ID and kick back and wait because you know that if there's an issue with the ID you have the cops at least very least he's going to go back to his vehicle to check so So you know you've got time because to me if you're in close proximity, he doesn't even have a chance to pull his weapon. He goes to grab something that cop's going to grab him. And he's going to overpower him.
Starting point is 01:04:03 He's an old man. He's in his 70s. Yeah. Well, even if he was in his 60s. In his 60s, I think of that time. But it just is, it's just an interesting, you know, thing for him, sort of like you, you know, are they, you know, you know who you are. Yeah. Nobody else does.
Starting point is 01:04:17 And you're in that situation directly with a police officer. Oh, I got pulled over multiple times with, with driver's licenses that I, but I got them all from the DMV, right? So I'd get pulled over and the cop would walk up and you know how fast you were going. I was like, how long you've been behind me? I was, I think I was doing 90 at one point and they're like, my gosh, at 82. I give him the ID and but I also know it's a real ID. Right. I know it's going to be fine. The car's in the say. I brought the car in that driver's license, that name's name. I've got full coverage insurance. Like I, I think I'm just think I'm that good. I wasn't concerned. Wasn't concerned because the cop didn't seem concerned. So I think that he probably would give him the
Starting point is 01:04:53 idea. And if he started feeling uncomfortable, like it's going wrong. Like, but the problem is too, you don't really know it's going wrong till the second cop car pulls up. And then you're like, ah, fuck. Now what do you do? Now there's, now there's possibly two to four cops, probably another car coming. What am I how many of these guys can I possibly get away? Right.
Starting point is 01:05:13 Am I going to go out in a blaze of glory? Right. Am I going to go back to prison? That would have been flashing through his head. Once again, he's older. He's older. Age changes you. Right.
Starting point is 01:05:21 The things that I did when I was in my late 20s and 30s, I look at at now and think, what an idiot? Like, what were you thinking? Like, I would never. But, you know, and he may be in the same way, like, fuck, you know, you start regretting your, your past decisions and what led you to that point in your life. So who knows what he was thinking. Yeah. Yeah. Doesn't mean you're not still an asshole. Um, so, okay, so they've got him. He talks, he talks, and he, for how long has he talked to him? He talked to him for the entire flight back. Right. And another interesting little thing that took place is as they're taking off, pretty early on in the flight, they're flying over the Grand Canyon.
Starting point is 01:06:01 So the other agents are looking out the window and Whitey Bulger said, what am I boring you? I'm sitting right here and he got pissed at the agents. What are you doing? You got me here to talk to. Who gives a crap? What's going on out the window? He wanted to talk.
Starting point is 01:06:17 And he never, Rich said he never stopped for a water break, never took a bathroom break, never asked for food. They offered him repeatedly. Do you want to take a break? And he's like, no, let's keep talking. He never fell asleep. If you sleep hot at night, you know how disruptive that can be. When you're not resting well, everything else feels harder. Your focus, your mood, even your recovery.
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Starting point is 01:07:50 bed in the world. Some exclusions apply. See sight for details. Which I probably would have. Even in Gustay, I probably would have dozed off. But he didn't, and he wanted to tell his story. And over the course of the flight, you know, his moods would change. He'd be reflective and then he'd get really angry. And there were a couple of times where he actually cried because he was talking about some things that happened while he was on the road and as a fugitive. And so it was kind of amazing thing for him to be, you know, talking about like that. So, and to see those change of, the change of attitude is hardened criminal, but an old man, like you say, just looking back. And I do think that he wanted to get something out there and that's what this was.
Starting point is 01:08:34 Yeah, I'm sure. So what? He gets back to Boston and he's, gets lawyers. Like he did, yeah, immediately. I'm assuming they don't let him use any of his own money to hire attorneys. He was asked that in Boston. They were asked, can you afford a lawyer? And he said, I could if you gave me my money back. Right. Everybody laughed, you know, a funny Irish little thing. And then they let him out. And so, yeah, so he ended up getting Jay Carney and Hank Brennan, who were two really good attorneys back home in Boston.
Starting point is 01:09:03 And they represented him during the trial. And why didn't he just plead guilty? Good question. You know what I'm saying? Like, why go to trial? I'm sure they're just offering him a life sentence, which he knows he's getting anyway. Right. They didn't cut a deal with him.
Starting point is 01:09:15 I guess the government didn't want to cut a deal with him after all this time. They wanted it out there. The government wanted a lot of this information out, too, because one of the things with the Bulger, the legacy of the Bulger, it's hard to overstate the legacy of the Bulger disaster for the FBI up in Boston because it totally compromised that office. Right. It destroyed its reputation in Boston. And it wasn't just Whitey Bulger. It was John Connolly. It was the previous guy, H. Paul Rico.
Starting point is 01:09:43 It was the whole informant program. There was a lot riding on it. Um, so they had to catch him. And then once they did catch him, they had to prosecute them fully. I don't think they were in any mood to get cut any kind of deal with Whitey Bulger. And they had the evidence. They had plenty of evidence. They had his old cohorts that literally told the FBI and the state police where the bodies were buried.
Starting point is 01:10:05 Right. And they were digging up those bodies in, in and around Boston while Whitey Bulger was still a fugitive. Um, yeah, but you still, I mean, you still have the right to just say, I'm not going to go to trial. I'll just plead guilty. Like, what is the charge? Like, so I'm, I'm wondering if he had an agenda when he played, I mean, when he went to trial, if he was like, no, I'll go to trial, was he thinking, I'm going to prove that this is all bullshit. And then I was actually a good, I was actually living off of, you know, taking care of my mother and living in her spare room. And I never did any of this stuff. And, you know, there was talk. And it was the subject of hearings back in, um, in federal court in Boston, that when Flemmy, before Flemmy decided to cooperate, he was making the claim that he and Boulder had a license to kill from the FBI. And they try to trace it back to a U.S. attorney, A. USA, who was dead. But that went on for a couple of years saying, we had a license to kill. We had this agreement with John Connolly, John Morris, and also now this
Starting point is 01:11:11 dead U.S. Assistant U.S. attorney, never written down anywhere. But that was the focus of a lot of things that were going on, a lot of hearings up in Boston. That kind of spawned the whole Black Masked book. That's where a lot of the stuff comes from. What are they called the, that, it's a public, there's a name for that when the FBI can't actually give you the right to break the law. Yeah. It's called, it's public something. I forget, but it's actually where they can say, hey, look, we're going to allow you to continue to sell drugs. When typically, if you have an inform, they go, okay, you understand you can't do this anymore, which they kind of know they're going to do it anyway.
Starting point is 01:11:50 But they can't condone it. So that's what that was their, that's what they were trying to do. There's no proof. There's no proof that there was any kind of agreement anywhere, and everybody ends up getting prosecuted. So maybe it was, you know, and that was the thought that when Whitey got caught, now all the chips are going to fall, now we're really, he must have a, the receipts that Flemy didn't have. Now we're going to find out, is there any kind of an agreement? Who else is helping him? So when Whitey got caught, a lot of people thought the FBI
Starting point is 01:12:19 was hiding Whitey the whole time. People still think that. The only reason why do you get caught is because the FBI said it's time to come in, let's go. But the truth is that when he had his moment to speak and he could have stood up in that courthouse and said, what are you talking about? You knew where I was. The only thing he cared about was that he was not. He was not, he was not remembered as a quote-unquote a rat. Right. That's the only thing that he cared about. What about, so that was kind of the agenda, his, his agenda, or his defense attorneys,
Starting point is 01:12:51 that's what they were pushing, was that, I'm assuming, during the trial. You know, he was, he was an informant, not that he necessarily didn't do these things, but, you know, the government is just as bad as what he bulger is. And, you know, there was, there's, that a defense? You know what I'm saying? That's what they were trying to say, you know, and that, and that, that, and that, was the focus of those that trial is his corruption trial for all those months did they ever call his brother to the stand no no what about uh connolly like he was connolly was incarcerated at the time
Starting point is 01:13:24 he wasn't called uh it was step and fleming you know they can call him i yeah but they didn't because that because he would have that would have made him eligible for uh uh uh rule 35 yeah he's out now yeah he's i mean i think if they had called him then they would have had to have given him something. Yeah. Most likely. Flemmy testified against him. All his old, all his old partners all testified. They all cut deals. They all testified against them. The deal with Materanah was especially tough for the feds because he was he was on the hook for like 12 murders and he got he got very little jail time. And he testified. Kevin Weeks testified. Flemy testified.
Starting point is 01:14:04 John Morris testified against him. John Connolly's supervisor testified against him. It was kind of a who's who, the Irish mob in Boston kind of lining up. They did call Patrick Knee, who was another kind of a rival to Whitey Bulger. They did call him and he had to show up to the courthouse and then they ended up not calling him to the stand. So that was kind of a interesting little development there. We all chased Patney around him outside the courthouse for a little bit. That was a little bit of drama.
Starting point is 01:14:30 Right. Why did he not get called? He wasn't cooperative. Who knows? Who knows what that was all about? And Pat is still alive and still and selfie. And not much is said about Pat to this day. And he was eventually found guilty and given what, how many life sentences.
Starting point is 01:14:48 You got two consecutive life sentences. Yeah, he knew he wasn't going anywhere. And that was it for him. You know, like I said, you know, why did he talk to Rich on the plane? Why did he detail all this stuff? And I think he wanted to get it out. He just wanted to get his story somehow out there. And it went into a 302 FBI file.
Starting point is 01:15:09 And that's what this is. So the 302, I think it just recently became public. Rich wrote that. But it's very matter of fact. You've seen those things. They're not the easiest things to read. And so, you know, luckily I was able to have Rich there with me. And he's the one who wrote and he had his notes and his memories and everything and
Starting point is 01:15:27 could kind of say, this is how this all went down. Here are the other things around it that took place while we were on the plane that are not in the 302. It's funny. I mean, I can see him wanting to tell the story because, I mean, first of all, he's famous. So he wants his version out there. And like, look at his brother who was a career politician and nobody knows who he is. If you know who he is at all, it's as a result of he's Whitey Bulger's brother. You know, he was, it's hard to overstate, too, how powerful he was.
Starting point is 01:15:59 up in Boston and to the point where when there was a presidential debate taking place at UMass Boston and Billy was the one who organized the whole thing. And at the same time that they're having that debate, just up the road, they're digging up the death pits. I've heard that in the backgrounds, like the you can see the Capitol building or something where they're digging up something. Yeah, yeah, yeah, you couldn't see the state house from there, but that's all happening right there at the same time. And it's just, it kind of tells you everything, doesn't it? Well, yeah, but it doesn't, I mean, it's when people say stuff like that. It makes you, it's like you're alluding the fact that maybe he was powerful and could have protected him, but I, that why would he, I don't, I, do you
Starting point is 01:16:44 think he would protect him at any point? Doesn't sound like he needed protection. It doesn't, you know. Why do you need a protection? Yeah, that his brother would have, was helping him in some way politically. Like, I don't see that he's in a position to really do that. Well, there was a story about Whitey leaving, going through Logan Airport with a bag of cash. Okay. And a Stady who worked there stopped him. And it was a whole scene. What he takes the bag, throws it to his cohort, Kevin Weeks, who takes off, whydy takes off and everything. And the Stady, who did all this, ended up getting demoted, getting sent to an.
Starting point is 01:17:23 another part of the state and eventually committed suicide. Now, there's a lot, we write about it in the book. There's a lot around that. That state he had some issues too. I think he had some PTSD. But there are a lot of people who believe that that happened because Billy wanted to know who it was that put the screws to Wighty at the airport that day. So, you know, you didn't have to go out and advertise it.
Starting point is 01:17:52 You just knew what he bought. is a powerful mobster and his brother happens to be one of the most powerful people in the state and i think people just kind of respected that that boundary you didn't have to put a sign out there might have to watch black mass again yeah uh it's not a horrible thing to do no so so why he ends up going to he gets sentenced then he goes to where does he go with prison yeah i did he go right to coleman i don't think you go right to Coleman, do you? He was out there for a while. And then he got in trouble because he was having relations with a female psychiatrist. Was he? And he got transferred out of there.
Starting point is 01:18:34 I think that's where he ended up. Where was he? He was in Florida, right? Yeah. So Coleman's about about an hour north of where we are right now. Oh, okay. So I'm getting it mixed up. He was out in Arizona. Okay. For most of his time. And that's where he was having the problems with the psychiatrist. Doesn't sound like you had a problem with it or all. Not at all, but when it got on Earth, then he comes out here to Coleman. So just a side note real quick. I was at Coleman in the medium when Whitey was at the pin temporarily. This is my understanding.
Starting point is 01:19:10 I'm almost positive. He was at the pin because this is what I had heard when I was there. Johnny Depp had made numerous requests to meet with him. He wants to get his mannerisms down. and Whitey would not meet with him. So what they did was the warden let Johnny Depp go to the pen and watch him on the video cameras for like an hour. Interesting. Where he was able to kind of watch his mannerisms, how he walked around and get as much as he could information as he could.
Starting point is 01:19:39 But I always thought that was funny because when that happened, like the guards were walking around the next day like, bro, Johnny Depp was next door. Yeah, he was there for like all day, maybe an hour. But yeah, they were like, yeah, they're doing some moody movie on Bulger. I don't know how long he was there because he wasn't killed there. No, no, he was at Hazleton, right? Right. Misery Mountain. Was that what it is?
Starting point is 01:19:59 But anyway, I thought that was interesting. Yeah, it is very interesting. And the Whitey Bulger that Johnny Depp saw isn't necessarily the Whitey that's in our book. And I first saw, he was an old man. He was in his 80s, right? And when I first saw Whitey at the courthouse in Boston when they brought him in, when they, you know, I didn't know what to expect. That was, you know, I had only seen Whitey in the, wanted posters and the handouts that the FBI would give, old photographs and everything.
Starting point is 01:20:25 You got that mean-looking young guy. And when he walked into the federal courthouse in Boston for his initial arraignment on these charges, he just looked like an old Santa Claus. He had the beard. He actually looked like he had a bit of a punch. And he almost looked like he was a little bit off, like mentally off. But I mean, a lot of criminals just age out of it. Yeah.
Starting point is 01:20:45 I'll tell you what, though. As the trial moved on, that was just my first time seeing him, which would have been at 2011. A couple of years later, he goes to trial. In between, there are other hearings that you go to. And the more I saw him, and granted, it was from a bit of a distance in a courtroom, but the more I saw him, the more you could see the actual gangster come out. And during his trial, you know, he was, he was mouthing off to some of the witnesses,
Starting point is 01:21:08 throwing F-bombs at people and, you know, kind of out of control. He wasn't really out of control, but he was showing his power. Do you know what he still had? Even at that diminished level, it was still there. I had a weird experience with him as that trial was getting started. And maybe this is nothing, but it's just weird. When they were in jury selection, I found myself in the courtroom before they were bringing in all the potential jurors with another reporter. And sitting at the defense table was Whitey Bulger and his defense attorney Hank Brennan.
Starting point is 01:21:43 And they're kind of deep in conversation. I'm in conversation over here with another reporter. When I just start looking at Whitey again and Whitey starts looking at me, then he looks at his, he starts talking to his defense attorney who then turns around, looks at me. You know, I can see what was going on. He was asking the defense attorney, who is this? I said that to the other reporter I was talking to. I said, Whitey's talking about us right now. And then I looked, I looked back at Whitey and now he's glaring at me. Right. And we locked eyes. And I thought, this is strange. what do I do?
Starting point is 01:22:18 Well, I'm just going to look back. He didn't do that. He didn't do that. He was more like this. And it was odd. It was weird. And then finally, eventually, he just kind of looked away and started talking to his lawyer. It just, there was no need for that.
Starting point is 01:22:35 It was strange. And it just made me think, you know, that's a side of Whitey. Rich mentions in the book that when Whitey was on the plane, that his emotions would change like that. He was crying at one point about a dead dog and about one of the people that helped him while he was a fugitive. And other times when he's talking about people he didn't like, he would throw into a rage. And Rich said it was almost like he was, you know, it looked to him like his eyes were changing color, but it was that kind of death glare. And so when Rich told me that, it flashed me back to my own experience, minor as it is. I don't want to overstate it or anything, but I said, you know what?
Starting point is 01:23:12 I think I saw a side of that personality when I was in the courtroom. Then he gets up, you know, they end up moving him for reasons we still don't know why. I think first to the Midwest for like a medical thing and then they send him out to Hazleton. He's killed within hours of getting there. Richard also. Who killed him? Sorry. Oh, some members of the Springfield mob up in Massachusetts who were tied to the, think the Genovese family.
Starting point is 01:23:36 They had in New York, but that's where they were. they were in Hazleton and Whitey just got was sent in general population and the word was out before even Whitey got there the word was out that he was coming to Hazleton and nobody knows why to this day nobody's sure why he got transferred there and why he wasn't segregated when he had enemies in that prison and he wasn't there very long before he was killed you know what's interesting about that is that because he's so old even though he has two life sentences he could go to a medium or he could go to, he could even go to a low. Like, there were guys in the low that had life sentences, you know, or they might have had 75 years or 40 years. I think there were guys, several guys
Starting point is 01:24:16 that had life sentences at the low. And at the medium at Coleman, like, there's almost no chance you're getting hurt. I mean, like, we're talking about like, even him, even if he was, even if there was a head out on him and everything, there are cops walking around. There are, there, there are DEA agents walk that are former DEA agents. And, and, and, FBI agents and police officers, police officers that had set up people, like drug dealers. And they're walking around with drug dealers. Like, they're like, there's, like it's nothing. So there are places they could have sent him where he would have been safe.
Starting point is 01:24:52 And the Bureau knows that. So it's odd that the Bureau would send him somewhere where they thought, hey, let's, and even to keep him in a pin, he's 80. Yeah. You could put this guy in a low. he's never leaving the low. If you made every mistake in the book, he's never getting out of that low. If you removed all of these COs for a week straight,
Starting point is 01:25:16 he could not get out of the low. I mean, there are multiple fences with barbed wire. Then they have the barbed wire ring where there's two layers of fence with Constitino wire and Constitino wire in between the two of them that there's no way you're getting through. and they're motion sensitive. Wow. The wind used to blow hard, and they'd call recall and lock everybody up.
Starting point is 01:25:40 Wow. Because the wind, it would shake it, and it would slightly shake it. That's sensitive. They're that sensitive. Wow. That at least during certain points of the year, at least four or five times of the year, because, you know, all it is is it's a tube with a wire in between something. So if it rocks and it hits together, it says, boom, this perimeter there,
Starting point is 01:26:02 but they would realize like, it's a fucking. win. You can see how bad everything's shaking. There's no ways getting out. You're just not getting out. And by the way, they have that perimeter trucks driving around. Yeah. So you're never getting out. So I don't know why you would put him in such, in a position where he's going to get killed. That's the open question. We don't know. So.
Starting point is 01:26:21 But you said, you said Rich was. So Rich was listening to, he was at, so during the trial, what he was held in Plymouth County up in Massachusetts. And that's where he would be at night. And then they would fly him or, drive him up to Boston for the trial, then drive back and forth. So Rich was listening and watching Whitey while he was in Plymouth as well. And he heard some conversations that what he was having with his brother while he was in custody waiting for the trial to end. And I just thought it was interesting.
Starting point is 01:26:52 You know, he did, there was something being said about, Rich thinks there's missing money. There's a lot of missing money out there in safe deposit boxes they were never able to find. and he listened to a conversation between Billy and Jimmy about a trip that Billy was going to take for Catholic charities that would take him to Spain, but he would have to transverse through Paris for some reason. I don't know why he flew into. I don't know the whole details of it, but Rich talks about it. And he thinks that Billy, he suspects Billy was checking on some money for him somehow. What he was going to do with it? How he was going to get the cash?
Starting point is 01:27:31 where it would go, don't know. But there's an, you know, like I said, there's $822,000 in cash. I showed you some pictures of it in the book. Whitey had millions. Where is it? Right. And, you know, there's a judgment for the families. They sued the federal government.
Starting point is 01:27:48 And they're, you know, they're supposed to get any of this money, but it's still out there somewhere. I think that's the last great mystery with Whitey Bulger is where is all that money? There's no way, you know, even though he said you should have caught me, you know, You know, if I had access to my money, he should have caught me 15 years ago. He said a lot of wise guy things after his capture. But he did not spend $20 million on the run. Yeah.
Starting point is 01:28:11 He did not live in the way it was not. Not living the way he was living, right? He didn't even have a computer. He didn't have access to the internet. I mean, he and Catherine, it was very analog. They were just analog in a digital age just living together. He would send her out on errands. He wasn't, they didn't go on vacations.
Starting point is 01:28:27 They didn't go anywhere. They went down to Vegas. He would cross, you know, to launder money. through the casinos, he would, like I said, would walk across the border. He didn't feel comfortable driving across the border into Mexico for his heart medication. And when he got older and he couldn't do that anymore, he had, under a fake name, he had Catherine go and get prescriptions. They did get a doctor to give prescriptions for his heart. But that was it. It's like any other retiree living on a fixed budget. Only this guy has access to at least 800,000 in his wall and possibly millions
Starting point is 01:28:59 more out there. And Rich said, you know, the thing after talking to him, he always realized that Bulger had a plan B and a C and a D. So if the heat was turned up on him in Santa Monica, which it had never happened in 16 years, but he likely planned for it and had an idea where he would go if he got wind of any kind of an effort of law enforcement honing in on him in Santa Monica, where would he go next? And Rich thinks that possibly somewhere else out in the southwest would be a likely landing spot for Whitey. How long did he stay in that? In Santa Monica, I think we're like five or six years.
Starting point is 01:29:32 He was there a long time. Right. In that apartment. Yeah. Yeah. That's probably a mistake. You know, if he had changed more, probably less likely that. It can't be easy to keep on the run when you're that old.
Starting point is 01:29:45 Yeah. And you also have somebody with you the whole time, too. And you're trying to keep her. Love, she seems like she has not spoken. She's out now. She did all of her time that she had, she got one of the longest sentences ever for harboring a fugitive. How long? I think it was over eight years. And it was extended because they were trying to find out where all this money was. So they were calling her before a grand jury,
Starting point is 01:30:08 and she refused to testify. And she said, I refuse to talk. Kevin Redington, actually, Lindsay Clancy's lawyer was her lawyer at the time. And I talked to Kevin about it. And he said, yeah, she just wouldn't talk. She wouldn't give up anything on Jimmy. So she did more time. But she's out now. We think she's living with her sister, who also was in communication with them. So I think the immediate Billy Bulger, I think the sister, McCusker, I think she also was in touch with them as well. But it seems like it was a one-way thing, arranged phone calls from somewhere else. It wasn't, I don't think they could pick up the phone and contact them. I think it was the other way around.
Starting point is 01:30:50 They had to go to, they went to somebody else's house and accepted and agreed to take a phone call. call from someplace. And that's how that was done. How did the how'd the book come out? How did it? Did you already know Rich? Did you already say that? I knew who Rich Deanne was. Okay. But I, I only met him briefly during the trial. And during the trial, he was tasked with bringing all the Whitey's guns and money into court every day. And then he was tasked with bringing it back and making sure that all $822,000 was accounted for and all the guns were accounted for. So I kind of chatted with him in the hallway a couple of times. And that was the extent of it.
Starting point is 01:31:27 I never interviewed him. Rich reached out to me about five, six years ago because he wanted to tell his story. And he felt that the story about Whitey's fugitive life about that flight back from Boston hadn't been told in the right detail. So he asked me if I wanted to work on a project with him. And for me, the first thing was, my first hurdle was, well, I'd love to work on a book. But what are we going to talk about Whitey Bulger? What are we going to say in this book that hasn't been said in Bolger? Black Mask the movie or Black Mask the book or any of about a dozen other books that are out there about Whitey Bulger.
Starting point is 01:32:01 What makes your story any different than that? Because I'm not interested in just telling the same old story. So then Rich started telling me about the flight, what happened on the flight. I got to look at some of his files. And then I realized that, yeah, we can talk about the fugitive life, what Whitey said. There's more information in the book, too, about why it took 16 years to find him, where Whitey went when he left Boston. that hasn't really been out there before. For example, the first time Whitey Bulger was on America's Most Wanted,
Starting point is 01:32:32 the FBI now knows that Whitey was in a hotel in New York City watching the show with his girlfriend. That had never been out there before. Is that groundbreaking new information? No, but it's interesting. It's interesting, isn't it? It tells you that he was aware of what was going on, obviously, in the news, and also he was aware on his own level that he was a wanted man and people were looking for him. Yeah, I remember watching that one.
Starting point is 01:33:02 They had sightings of him like in England where they believed. I remember thinking, wow, this guy is like he's in Europe right now somewhere, probably, probably retired somewhere there. He was in Europe, but it was before he was a future. And he got into a fight with a guy out there in England. He got a fight with somebody who called him a Yank. and he got in fight with him on a train. And, you know, blood was drawn. And this guy was kind of, obviously,
Starting point is 01:33:27 he had to be kind of crazy for what he, you know. Right. But he was hot-tempered guy. And, you know, all that's in the book. He talked about it. And he talked about his perceived near misses when he thought he was being recognized. Or he would start arguing with somebody, throwing F-bombs and everything. And then he had to cool down because I realized I'm going to get some attention.
Starting point is 01:33:46 Yeah, I can't have the cop show up here. Can't have this. And that all happened. But from what we understand, the entire time Whitey Bulger was a fugitive, he was in the United States other than crossing over the border to get some heart medications from time to time. And he never, and he never wanted to leave. Like, you never thought, hey, I'd do way better internationally. Oh, well, it's interesting. When Whitey was trying to figure out where he wanted to land and spend his time as a
Starting point is 01:34:14 fugitive, he did think about the Northwest, maybe into Canada, but he didn't like the weather. Right. He thought it was too cold, too rainy, too depressing. And just like every other retiree decided, I can't do that. Now, there's another, when they were looking for him, one place that they looked for more clues was in Montreal because he had a safe deposit box up in Montreal, Canada. And the person that was kind of not in charge of it, but he was a member of the Boston Bruins is Chris Neeland. That was his kind of his son-in-law. And they interviewed, the FBI went interviewed Pat Burns, who was the coach of the Boston Bruins. You ever see Jim Bolter?
Starting point is 01:34:56 And he said, we thought that was Uncle Charlie. He would be in the locker room with us and he'd go out to dinner with us. And there was $15,000. Chris Neeland told them that he got in trouble with Whitey because when he got traded to another team, he was on the Canadians at the time. He cleaned out Whitey's safe deposit box, which had $15,000 in cash and brought it back. and why he just about lost his mind? You're like, don't you ever touch my money again?
Starting point is 01:35:23 And it freaked kneeling out. Right. Yeah, I had heard that one of the places they thought he might be was Ireland. Sure. Right. Made a lot of sense because of the Valhalla. Right. Right.
Starting point is 01:35:36 But then you wonder, you know, would the IRA want that kind of heat? Right. For a guy who's running some guns and that what happened, the boat got intercepted and the whole thing blew apart. But do you know that were there ever, well, first of all, he was willing and offered, whether it worked or not, that's not his fault. Right. And but secondly, were there other successful missions? It's possible in that he may have given money prior. He may have done, you know, supported them in other ways. And that would be a reward for your loyalty to us back during the troubles. Maybe, maybe. But I just wonder, you know, is that more trouble than it's worth.
Starting point is 01:36:12 Yeah. No. Somebody like that there. Your best bet is to just go where nobody knows you. Stay away from everybody because at some point these fear, oh, no, these criminals will hide me. No, these criminals will eventually get caught and they will use you as a bargaining chip to get out of what they've been arrested for. So that's probably wise not to. Plus, you know, most people think it's very difficult to get a passport, right? Like he doesn't have a passport in this, this, these fake IDs names. Really, he has all the, he has all the tools he needs or all the documentation he needs to get a passport. He probably just thought, Jesus, people think there's a huge amount of scrutiny,
Starting point is 01:36:51 but the real scrutiny is the driver's license. Once you've got that and the birth certificate and social security card, you really don't need anything else. You're going to get one unless this guy owes back child support or back taxes or something, which I'm sure he doesn't. So, you know, I think he, you know, like we said before, it's easy to plan to make an escape, to make a break, to get away. And he did all that.
Starting point is 01:37:13 He had money squirled away in different places, but he didn't really have a plan of where he was going to go. And he kind of just settled on Santa Monica. And once he got comfortable there, that's just where he stayed. And maybe, you know, leaving the country at some point to go start all over again, maybe that just didn't appeal to him. Guy in his, you know, mid to late 70s pushing 80 at the time that he was caught. Maybe he was just like, I don't need to do that. I'm just going to stay right here. Yeah.
Starting point is 01:37:38 There was a, there's a sports bar near where he was caught. and it's a Boston sports bar. And I went there in 2018 because the Red Sox were in the World Series. Whitey Bulger was still alive. And we're just doing these fan stories. I don't always do crime stories. Sometimes I do very light stories. And I was sent out there to do stories about the Red Sox in the World Series.
Starting point is 01:38:00 And I went over to the bar and I talked to the owner. I said, do you think Whitey ever came here to cheer on the Patriots when they were going through their thing in the Red Sox and all that sort of thing? And he said, you know, you never know, maybe. He also had a, I think he had a niece that lived out there, too, not that far away. So it's not inconceivable that he had some visitors out there during his time. And he wouldn't talk about people who were alive, so he didn't talk about it to Rich. If someone wants to buy the book, where can they go? Yeah, the name of the book is Face to Face with Whitey Bulger and FBI agent's account of capturing
Starting point is 01:38:31 and debriefing Boston's most notorious gangster, written by myself, Bob Ward, with Rich Tien, who's the FBI agent, who's the subject to this book. The book is available on all the major online retailers on Amazon, Barnes & Noble, anywhere. You can order it there. And also from our publisher, which is McFarlane Books Exposite as well, which is an imprint of McFarland. They're selling it as well. I think it's on sale right now, too. Hey, you guys.
Starting point is 01:38:57 I really appreciate you watching. Do me favor. Hit the subscribe button. Hit the bell so get notified of videos just like this. Also, if you want to contact Bob or buy the book, go into the description box. We're going to leave all of his links and the Amazon link directly. to buy the book. Thank you.
Starting point is 01:39:12 Do you have an, do you have an Audible version? Not yet. We're working on it. What's, what's, people love Audible. We'll chat about that. Anyway, thank you very much.
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