Episode 1: Face to Face with Whitey Bulger

Well, there's been no shortage of Whitey Bulger books over the years, but there's a new one out now that covers some ground that many of us haven't heard about and can only wonder what really happened. The book is called Face to Face with Whitey Bulger. It's written by FBI agent and head of the Bulger Task Force, Rich Tehan, along with Boston 25's own Bob Ward, and it covers Rich and Whitey coming back to Boston, flying from California after he was captured. We had him for six hours, Rich, captive audience there. Before we get into the book, though, Quincy guy, Franklin guy, this is as local as you get. You've covered the Bulger case for years. You obviously were right there knee deep in all of it. Tell us first how you guys wound up getting hooked up in this project. Well, I knew about Bob's reporting over the years. I came back to Boston in 2006 and he had a stellar reputation and I followed Unsolved, his Unsolved show. And so when I got the idea to start writing, it was funny. A mutual friend of ours, after Whitey was captured, he sent me a blank journal and he wrote me a note. He said, start your story. And I started it, but I didn't. I took my time and it evolved into wanting to write a book. And there had been so many books being written that I wanted to tell my story and it had never been told before. Somebody could trust you because I know as you write in the book, there were some members of Boston media who weren't as cooperative or wouldn't be as cooperative based on your experience. One hundred percent. Yeah. And Bob, you obviously, I mean, I would imagine jumped at this opportunity. Absolutely. When it came my way, I always wanted to write a book, but I never knew what I would write about. I knew that I needed a good story to write about to hold the public's interest. So our mutual friend recommended me. One day, Rich contacted me. Now, when the Whitey case was going on, I didn't meet you. I met you during the Whitey Bulger trial. I heard of him, but I never I didn't have a business relationship with Rich at all. So when Rich reached out to me, my first question is, all right, there are other books about Whitey. You know, what's different about your story? And I was a little skeptical. I needed to poke the bear a little bit and see what was there. And I think the, you know, the light went off over my head when I realized, wait a minute, you were six hours of Whitey Bulger on a plane. I don't know of any other lengthy interview with Whitey Bulger, whether definitely not with in the press, and I doubt highly there's any interview with law enforcement other than what you did. And when Rich started telling me more about his story, his time on the task force, how the task force was really divided and was almost fighting itself for a lot of years, I realized this is a story that needs to be told. So when you you got the call and you found out, first of all, you're going to be flying back with Whitey Bulger and the FBI plane back to to the G.V. Right. As we call it, sure. OK. Or the V for the V for victory. Yeah. He sits down and you're with him face to face talking about it. What was your impression of him, given you had learned so much about him through all of your investigation, all of the stories you heard, all the stories we all knew this was a guy who's been, you know, involved in all of these crimes, all of these murders. What struck you most about him when you saw him for the first time? You know, it was a surreal experience, to be honest with you, because as a fugitive investigator, it's not often that you can speak with your foe for, you know, six hours uninterrupted. He tried to control the conversation the whole time. We would have to bring him back on task. We wanted to know what his playbook was for being on the run for 16 years. And what struck me about him was how articulate he was, high IQ, but very, very, very narcissistic. Extremely so. And Captain Greg was along as well, who didn't participate in the interview while you were flying back, but she was present. We separated them by intent just so they wouldn't play off each other. And we isolated him on the back of the aircraft and he spoke for six hours uninterrupted, no break, no water, no bathroom, no food, no nothing. And going through the interrogation, if you will, Bob, what jumped out at you most from that, given your background and knowledge of the case? Just his change of mood, as described by Rich, how he could be sullen, one minute contemplative, and then just in a flash he would express rage and he would be really angry. And Rich and Phil Torsney, another agent who was on the plane, there were two of them on the plane, had to bring him back, had to ground him to make sure that he didn't go way off topic or didn't completely shut down and refuse to say anything. So it was all those mood changes in that short span of time that really struck me. And you saw the volatility there that he was notorious for. Yes. And it's funny, what I noticed about him is one minute he was emotional and crying when speaking about a person that he had manipulated, James Lawler, who had passed away while he was on the run. And one minute he's crying and then the next minute his eyes would change and his facial features would change and his eyes would turn color almost. It was quite something to see. But then he would go back and forth, go back and forth. And we had to keep him on task. But he was eager at the same time. Yes. And didn't say, well, I'm not answering that really. Although, as you said, he would take you down a different path, maybe from the question you're originally at. Yes. At points in time, he would say, you know, I shouldn't be speaking to you guys about this. You know, you arrested my brother, Jackie. And we would have to kind of like bring him back to to talk with us and and not shut down. And Bob, in seeing Whitey at the trial and knowing what Rich has written about him on that flight and told you about on that flight, he doesn't didn't really come across at that point anyway, as this notorious, bloodthirsty mobster. No. When I first saw him at his arraignment of federal court here in Boston, I was kind of shocked. I remember watching him come in right off the plane. Yeah. And I thought to myself, that's Whitey Bulger. And he kind of had a I thought he had a paunch. He had the beard and didn't look like the menacing guy that I'd seen in all those mug shots. And he even was kind of looking around and joking. And there was a question about whether he could afford an attorney. And he said he just said, oh, I could if he gave me my money back. And everybody laughed about that. And he kind of looked like this Southie Irish guy, witty. And, you know, that's what I think type of guy you meet at a bar. You didn't see the killer. You didn't I didn't see the volatility that day. Right. I did see it during the trial because during the trial, he was mouthing off to Stephen Fleming, to Kevin Weeks, and some of the victims would get up and yell at him and he would yell back throwing F-bombs. I finally was able to see that over time. Sure. Let's go back before the flight and talk about how he was finally captured in our next episode. We're going to get into the things you uncovered and how he stayed on the lam for 16 years. But when you finally said, OK, because you came up with a plan that kind of worked for you with pretty good success when you were in the FBI office in Connecticut and people were reluctant. You had a supervisor who was reluctant. I don't know if this is going to work. Should we really do it? But explain what you did and how it all did come to fruition. And you were able to finally track him down. The original plan and the original investigative goal was to capture him. Right around 2010, we started to focus on Katherine Gregg. She was a dental hygienist and she had had plastic surgery. And so the team, the investigative team, went out and got very, very enhanced digital photos of her. And we started with dental associations and we started with plastic surgery associations. We got some leads in Canada, up in Victoria, Canada, which turned out, you know, to be lookalikes. And so that so we decided as an agency to come up with a public service announcement. And it was 30 seconds. It was we had a budget of about fifty thousand dollars and we hit 14 media markets around the country where we had leads for Bulger before. And we focused on the daytime female audience. And lo and behold, we aired it on June 20th, 2011. And on June 22nd, we received a tip through that. The really cool thing about it was it had caught on because it had never been done. The FBI had never done this before. And so CNN caught on and BBC and national media paid the 50 grand for it. But you get a lot of free publicity from other news outlets that help spread the word. Yes. Yeah. Yes, for sure. And so it went worldwide. And lo and behold, we got the tip that that ultimately caught him. So I want to ask you something else. And Bob, you can weigh in on this, too, because you've heard the stories. All the FBI knows where he is. They they're hiding. Well, Whitey, for all we know, they're supporting him. And then you put this tip out. No, just two days later, all of a sudden this this tip comes in. How do you deal with that skepticism and that sort of criticism in a way? And does that even matter? Since at the end of the day, you got the guy you were after, albeit 16 years later, but you did get. Yeah. You know, we just ignored the noise. We really did. And we had people coming out of the woodwork, you know, both for the reward, but also to claim credit for for tips in the past. Right. And we just ignored all the noise and focused on who helped him, you know, be on the run for that long and who may have harbored him throughout his 16 year campaign. The only thing you write about in the book, Bob, too, is is all of the leads that you had to track down. I mean, you guys were truly this was truly an international operation on the part of the FBI. Yeah. I mean, I don't think there was a stone left unturned to try to find Whitey. The other thing, too, is that Whitey Bulger looks just like every other senior citizen. Right. He was in his 70s at the time. Right. When you were looking for him and and then you finally saw him when they caught him. I don't know if I would have recognized him if I was in Santa Monica and I actually saw him and I was looking at his pictures and doing stories on him. So they had a lot of lookalike sightings. Rich was even following up lookalike sightings when he wasn't even on the task force, when he was still in New Haven and and going abroad and trying to to run this stuff down. There was one store, one lookalike that made international news of a couple in Sicily, Taramina, because there was somebody on vacation, took some video and thought that could be Whitey, that could be Catherine. And they had to run that down. And it took a long time to run that down. But that was major news. So just think of the effort it takes to chase down some of these lookalike sightings and and how you sift through and find out which one is legit and which one isn't. And that noise that you talked about was really deafening. You know, I was there for that. That's when I was covering it. And that that attitude that the FBI is no interest in catching Whitey because of John Connolly, the corrupt agent who gave Whitey the the slip and gave them the advice he and Fleming that the indictments were coming and then previous cases ahead of that. There was good reason to be skeptical about it. But these guys just went and did their job. And in the book, it isn't just Rich's word. There are other people that were on the task force that don't get a lot of attention and a lot of acclaim. They were working it, too, from the very beginning. And they were running into some serious problems with other law enforcement. So it seemed like for the longest time before Rich got there, law enforcement was fighting amongst themselves. It was the FBI over here and the state police over here and the marshals over there and no cooperation, even though there was a task force. And it was so bad. The task force within the FBI itself, you guys had to move out of the FBI headquarters in Boston to an entirely different building because there was concern there, you know, there could be more leaks or someone else digging information. And who knows? Yeah, it was an offsite location. And we kept all the files in a vault inside of our office. And we just didn't want anybody compromising anything, leaking information, that type of thing. We were separate from the office itself. And even after Whitey was caught, one of the first calls he got when he got back to Boston was from the FBI director who wanted to know, what did he tell you? Who else is he talking about? And that just shows you that even within the bureau all the way to the top, there was that there was some doubt. Who else did Whitey Bulger corrupt? How deep is this? Right. And that was a concern because you didn't know who you could trust. Correct. Yeah. So I mean, that's pretty, pretty remarkable. Yeah. And then you talk about quickly also the relationship or lack thereof with some other law enforcement and state police. You guys kind of you could you need the spirit of cooperation. You need to share information. You need to tell each other what's going on because ultimately the goal is the same. But that was not the case at all. No, we had a dedicated task force with and there were agencies that would flow in and out. Boston PD, Department of Corrections was there throughout the whole task force life of it. And the Massachusetts police did represent, but there were elements with the state police and the DEA that just did not think the FBI was doing the right thing. They thought that virtually the entire core of FBI were were corrupt. And they put stuff together without telling you guys and trying to, you know, the situation with Kevin Weeks, where they had him under surveillance and then he got away and then the whole driver's license situation as well, Bob, that that really you look at it now and go, well, if you had maybe cooperate and everybody's on the same page, yeah, maybe this would have ended a lot sooner. When Rich first told me about some of these ideas that the state police were doing, I thought, well, that seems like a good idea, you know, on the surface. I'm not I'm not a law enforcement guy, you know, and the idea was if we can get Kevin Weeks to unwittingly pass along, we'll get him some I.D. material, the raw material for I.D.'s like a birth certificate. Whitey makes an I.D. out of that and then he gets pulled over for speeding or tries to get on a plane. Bang. We got him. We know who he is and we'll go get him. And that is what they tried to do. It was a legitimate birth certificate that was torn out of a register. And we have a picture of it in our book. It was entered as evidence in the trial, but it didn't come up in the trial. That was secretly passed to Kevin Weeks through certain channels and out to Whitey Bulger. And you had heard about it when you got there. He couldn't believe it. And when you went to Whitey's apartment and saw everything laid out, sure enough, there is that birth certificate and that picture is in the book. But explain, Rich, why that was not a good idea, why that could have ended in disaster. He could have committed crimes using, you know, alias names that that he had been provided by law enforcement. And simply put, you know, it just was not a good idea to give him fake names, you know, legitimate alias names for, you know, use that he could manipulate. Wasn't there a concern about him creating a passport and getting out of the country? Yes. And then he never find him. He was using multiple. Yeah. All right. So we got much more to talk about. They're going to take care of our first episode, our next episode. We're going to find out exactly how Whitey Bulger managed to stay on the run for 16 years based on the conversation he had with Rich on that six hour flight back to Boston after his death.