Episode 3: Face to Face with Whitey Bulger

We're continuing our conversation about the new book, Face to Face with Waddy Bulger, which was written by the former FBI agent, the head of the Bulger task force, Rich Tehan, and of course, Boston 25's own Bob Ward, as they teamed up to write this book together. You want to learn about how that happened? Well, that's in our first episode. But we want to talk now, as we've continued, we've learned about his life on the lam, how he was able to do it, how he was funded, how he was well-armed. But also, what we want to talk about in this segment is how there were other opportunities to get him. And there was one in particular because, first of all, Rich, tell us when you're in a situation and you've tried everything and nothing's coming together and you feel like forces are working against you, what is the process like of like coming up with plans and you sit down as a group and kind of just sort of spitball things, if you will, about, okay, well, what else can we possibly do here? Who's got ideas? And is that what it came to at some point during all of this for you guys? Yeah, for certain. I mean, you know, a case that as large as this, you know, for 16 years, we had well over 125,000 documents in the case file, volumes and volumes of testimony. And we had to come up with projects inside of the case that would ultimately, you know, One of the ideas, and, you know, this was an investigative step that people do utilize. And when you do go after fugitives, you look at the family first, and then you work your way out. One of the steps we took was to try and indict Billy Bulger for perjury and obstruction of justice for taking phone calls from his brother. Which he had denied. Correct. Correct. And, and ultimately, we went to the US Attorney's Office, and we wanted an indictment. And ultimately, you know, we thought that was going to work, because it would, it would draw him out. And I really think it would have worked after speaking with him. He didn't want his brother to take the heat for him. So you the thinking being, okay, we go after Billy, why he doesn't like that. And he says, Okay, I'm protecting my brother, I'm here to stop what you're doing with him. And, and you got me now. And Billy was taking a lot of heat before, you know, as all this is going on, if you remember, the Boston Globe ran story about grand jury testimony about that phone call, and there were congressional hearings, and he got called Billy Bulger got called to Washington to testify. And that's when he said, I don't recall, I can't seem to recall this, that other thing, pleading the fifth. And it was, that is what prompted then Governor Romney to push to have Billy Bulger removed from the presidency of the UMass system. So Billy was already paying a very high price. He was on the ropes here. And at the same time, this plan was being hatched, if you will, put into play to try to smoke out Whitey by continuing to apply that pressure to Billy Bulger. And you've got you had what you thought was a pretty good plan. And everybody seemed to be on board. Yeah, almost everybody. Yeah, I mean, we had, we had been given an opinion by DOJ main justice, that it was a circumstantial case, but it was a tribal case. So the investigative team thought that would really work. And, you know, ultimately, it was decided not to indict him. They waited till the statute ran. And ultimately, the US attorney at the time decided, Michael Sullivan was at the time. Now, he did come to the task force and explain, attempted to explain his decision on that, right? He did. And, you know, we can agree to disagree on that all day long. With his opinion, and his justification for not, you know, prosecuting him, it's the whole blood is thicker than water, you know, opinion. And I don't think that holds any meaning, the jury would say, well, he was protecting his brother. So yeah, you know, you may not get the the end result that you were hoping for, you wouldn't get the jury appeal. Right. And I didn't agree with that. But I thought that was a tribal case. And, you know, at the end of the day, my opinion is that politics came into play. Right. And you and I want to follow up in just a second. But in the book, you say, you guys would get close, and you would have leads and you but something, you know, you couldn't quite put your finger on it was always not kind of getting in the way. Yeah, I mean, there were forces at play that were working against us. They just didn't believe that we were taking it seriously. And there were there were people out there that thought that we were hiding him. And, you know, I knew the real deal at the end of the day. And, you know, from everybody from the media, to other, you know, law enforcement agencies, they thought we weren't serious about it. And the other thing, too, and Bob, you guys write about this in the book, is not only was that an opportunity, you guys looked at it and miss, but you'd worked so hard on it. You've been so close before that it was demoralizing to everybody else on the task. Yeah, it had a devastating effect to the people on the task force, not just rich, we talked to other people around that task force. And they some of them had been on that task force for years. And there was enthusiasm. You were saying there was there was a lift in everyone's step, they felt we're going to get him out, this is going to work. And it was had a devastating impact on the task force. Some members said, that's it, I don't want any part of this. Because if we can't do that, we're not serious about finding whitey balls or bringing anyone to justice. What are we doing here? And I think that in the this first time that this has been reported in our book, that the impact of that decision not to prosecute directly led to whitey's capture in a roundabout way. And that it forced rich and the rest of the people who then there were other people then came into the task force that were from other places they come on, it forced them to say, what do we have to do to find this guy, we've tried all of this, we need to try something else. And if they didn't have that pivot, they may not have caught white. So the whole thing about not going after Billy Bulger, you know, for whatever reason that took place, it had, I think there was a direct line from that to, ironically enough, actually capturing whitey Bulger about five years later, I think it was. So as crushing as it was, it led to the it eventually did. But it was a long and twisted road to get there when it there's no, you know what, here's the thing. It's Monday morning We don't know if that would have smoked whitey out of Santa Monica. We honestly don't know. Jackie Bulger, his other brother, gotten all kinds of trouble for helping his brother with fake IDs. And he was brought in. He was arrested, he lost his pension, he did some time, I think that didn't smoke whitey out. Would it would Billy Bulger, who was already paying a high price, his whole career was blown up, his, his legacy was blown up. Why didn't come out of the woods for that either? So we don't know. All we do know is that eventually that decision turns out to have been a pivotal key moment in how this all ended up playing out. So something else we don't know. And again, it's speculating. Had you gotten the cooperation earlier from other law enforcement in the area, and then perhaps this situation? Is it possible why he could have been caught a lot earlier than he was? Yes, I believe so. If there was cooperation across the board, I think he could have been caught down in Grand Isle. I think he could have been caught possibly in Chicago. But everybody was siloed. Everybody was having competing investigations, which led to, you know, which led to him being able to be on the run for that long. And also in New York, in New York, the library when Kevin was bringing those raw materials to the IDs, no one was following that trail. And one of your informants was actually in Long Island saying, why don't you go up and touch the hood of the car because he's in there, go get him. And that all kind of fell apart. And it's, it's very frustrating, heartbreaking to think that why he could have been caught, I believe, within the first 12, 18 months, something like that, he could have been caught and brought in. But then that's the lesson of the book. You know, that when law enforcement is not all on the same page, bad things can happen. And it did. And he just ran right up the middle and was able to get away. And there was another huge lucky break in this. And that was Teresa Stanley. When she got upset when she found out about Catherine Gregg, she revealed the ID not directly to the FBI, but to an informant who told the FBI. And when she figured out what happened, she told Kevin Weeks, Kevin Weeks got that message to Whitey. And that forced him to change everything. He was no longer Tom Baxter after that. But also it forced him to cut all his ties back to his, his people up here in South Boston. He knew he couldn't, he couldn't trust anybody in his crew. Once he, so once he got on that train, he and Catherine got on that train and went out to California. That was it. There was no more Tom Baxter. There was no James Whitey Bulger. And he went out to California. I think he still had the Baxter ID or one of the other ones, but he wasn't sure who he was going to be either. He just knew he had to rely on his smarts and nobody back here knew what, where he was going or what he was doing. It was just him. And that's another reason why it took so long to catch him. One of the other things too, in the book, which is, it was just a great story, a couple of things related to Las Vegas. He would have that old cash. And so he would take that old cash, go to Vegas, get some chips. And then after, you know, whatever tournament and get fresh cash, so that wouldn't be able to track him. It wouldn't be like, wait a minute, this money's old. It's out of date. It's uncirculated. He had money that was actually going on then. But the other part of the story is that one time, I think it was going back to California from Vegas, where there were people on the side of the road, had a flat tire. And in the story he claimed to you, Rich, is that, you know, he kind of helped them out. And those, again, people had no idea who he was, but that potentially could have ended badly. It could have, but you know, he, he had faith in his, in his alias ID. He had faith in that Lawler ID. So he traveled with impunity. And it turns out for good reason. I mean, yeah. Yeah. Yeah. And, you know, he talked about, you know, driving back to Boston or coming back to Boston to settle old scores. That was pretty bold. That was a bold move. Sure was. But it shows that he had faith in what he was doing. He said he claimed that he came back to Boston disguised and armed to the teeth to, to find somebody he had beef with. We think we know who it was, but I don't want to say because it could be wrong about that, but he came back here. And I, I've since, since we wrote the book, I've since talked to other people in Southie who said, I've heard about Whitey being here. I know people who have seen him when he was here for however long that was, we don't have a timeline on when that happened or how long he was here, but it appears that he was here in disguise. He liked to wear disguises and wore disguise in one of the hits and on the sea, in the seaport. So all of that, I, you know, you might think he's lying about that. He's being, you know, an element of bravado, but I, he was telling the truth about everything else. I don't know why he would make up a story about coming back here. He had Lawler's car, he had a disguise, he had another ID and, um, you know, it's, it would fit his, his personality to just go do this. I'm going to travel 3000 miles and go back to Southie and I'm going to, I'm going to go after whoever it was. Couldn't find them and had to go back. Yeah. We tried to press him on the aircraft and he would not talk about it. He wouldn't elaborate on it. He wouldn't tell us when, uh, it was, you know, I pressed him pretty hard and he just would not elaborate on who, when, how and why that was his unfinished business. And who knows, maybe he thought I'll find another way to get to my target. Right. We talked earlier in an earlier episode about the corruption with the FBI, with the John Connolly, John Morris as well. Uh, his handlers tipped him off. John Connolly did that, put a stain on the FBI. It led to some problems. People trusting the FBI with state police and other things here. Um, that's in the past has the reputation of the FBI. Uh, and I know you're out of the game now. Has it improved? Has that stain been removed? Or is that sort of a wound that will fester and bleed, but never heal? I think it has, I think it's been removed. I think that we have good partnerships with state police and the DEA, other federal agencies. That's my opinion. You know, I've, I've been retired since 2017, but I think the best thing that could have happened was that the FBI arrested him and, and they arrested him in, you know, without injury and without a confrontation out in LA. And I just think it was a full circle moment for the, for the Bureau. And I think it really, um, showed the public that we were serious about finding them. Interesting, Bob. And I know you love this aspect of it. Rich takes down, brings in one of the most notorious mobsters in Boston history, but his dad also was involved in a similar case years before in the sixties with Albert DeSalvo, the Boston strangler and a pretty remarkable picture. Talk about that. It's one of those things that, you know, Rich, Rich is a humble guy, you know, and I was, we had hours and hours of interview sessions. And one day we were just talking about his past and he just brought up how his dad, we talked about his dad and he said, Oh yeah, dad was a, on the state police. And he escorted Albert DeSalvo out of the Lynn police station, right. For a court hearing. And I said, what do you mean? And he said, and I'd forgot about all this. So DeSalvo had been captured, but then he escaped and then he gave himself up. And so it was a big deal back in the mid sixties. And he said, Oh, and I've got a picture. It's a, it's a big deal in our house. This is my dad right next to Albert DeSalvo. And sure enough, there it is. Your dad escorting Albert DeSalvo, the Boston strangler into a cruiser in Massachusetts back in the mid 1960s. But even before that, Rich had a run-in with, not a run-in, but kind of met, knew who Whitey Bulger was when you were just a boy, right? That whole Joe's off of the expressway exactly. Yeah. Your dad took you there and then there, he said, look at these guys over here. Yeah. We went out to breakfast every Saturday or Sunday and we would go to Hojo's. It was nice and close to my house. And one day we were sitting in there and he just said to me, you know, there was a group of older guys in the corner and he just said, you know, look over there, Rich, those guys, you don't, you know, you don't want to be involved with them. And he told me who they were. And I, you know, I filed it. I was a little kid, but you know, it's just ironic that I, you know, I ran into them. And then you wind up being, you know, the guy who, who brings him home to face justice. That's, that's pretty remarkable. It is remarkable. It's funny how life works sometimes, you know. I want to ask you both this final question as we wrap this up. Could it be possible for someone like a Whitey Bulger to exist now? Could this whole situation ever happen again? With all of the crimes he committed, with the corruption that helped him get away with things, to him being on the lam and hiding in plain sight for as long as he did, is this a sort of a one-off or have we advanced to the point now with cameras everywhere, with the technology we have, with phones, that we'll never see this type of thing again? No, I believe that we will not. With the advent of social media and with the technology behind cell phones and literally there are cameras everywhere. I don't believe this will happen again. I don't think law, I think law enforcement has advanced itself so much so technologically that I don't think it could ever happen again. And a lot of amateur sleuths out there too, Bob. Yeah, there are a lot of eyes out there looking and there was a two million dollar reward here. So there's a good, you know, people, amateur sleuths have a good reason, good motive to try to find somebody like a Whitey Bulger or whoever the fugitive is. I think the only way a Whitey Bulger could exist now is if they were somehow able to get themselves out of the United States to some remote place where they don't stand out and they can just live off the grid. Because you're right, there are cameras everywhere and every year there are more and more of them. I remember covering the Tsarnaev trial and I was looking at the evidence in that. I could not believe all the photos there were out on Boylston Street around when the bomb, those bombs were actually exploded and what happened. It was brutal seeing all those images and that was back then. And now here we are in, you know, 2026 and there are even more cameras out there. So it would be really difficult. I think it'd be a lot more difficult too just to create a fake ID the way he, you know, the way he did. I'm sure, I know it can be done, but it's just not easy. And whoever the person is trying to stay on the land would have to be incredibly tech savvy, I believe, to be able to be as successful as Whitey was. The book is Face to Face Whitey Bulger. It's fantastic. You're going to learn things about this case. You think you know everything about Whitey Bulger. This book covers some new ground and you'll be glad you picked it up. And by the way, we're getting closer to the summertime. Couldn't ask for a better beach read than this. So I can't say enough about it. And I'm not just saying that Bob, because you're my colleague. I told you it's terrific storytelling in here too, besides getting all that information out there. I think folks are really going to enjoy it. And again, some ground that has not been covered is covered in this book. Rich, congratulations on the book. Great job. Appreciate it. Bob, I see you every day. I'll see you around. All right. Thanks a lot, guys. You got it. Thank you.