Robert Fitzpatrick was the dogged FBI agent who tirelessly followed the truth, and sought for decades to arrest the notorious alleged murderer and head of the Winter Hill Gang in Boston, Massachusetts. Jon Land is the thriller author who introduced me to Robert Fitzpatrick and the book, Betrayal, that they co-wrote about the Whitey Bulger case and how some FBI agents, for reasons of their own, allowed Bulger to continue to operate his crime syndicate for years after becoming aware of his illegal activities.
The subtitle of Betrayal is “Whitey Bulger and the FBI Agent Who Fought to Bring Him Down.” When I heard that Whitey Bulger had finally been captured, and that he was headed to trial, I immediately thought of my connections to the case and thought that here was another chance to let Jon Land and Robert Fitzpatrick tell the world about the Whitey Bulger case, and why Robert eventually felt a sense of betrayal by the very organization that he loyally served, the FBI.
What follows is my recent interview with both of the authors of Betrayal, Jon Land and Robert Fitzpatrick. I begin the interview with questions for Jon Land.
Douglas Cobb: Jon, could you tell our readers how you first heard about the Whitey Bulger case, and were you interested right from the beginning in co-authoring Betrayal with FBI chief Robert Fitzpatrick?
Jon Land: Well, it’s impossible to live in New England and not be familiar with Whitey Bulger—he’s been a staple in the news for a generation now. But what interested me in the book was meeting Bob Fitzpatrick. I had a gut reaction as soon as we shook hands and twenty minutes into our lunch I knew I was talking to the kind of real life hero I strive to have my fictional heroes emulate. Beyond that, this was one of one of those rare nonfiction stories that had three acts: a beginning, a middle and end. Even before Bulger was captured that end was a 2006 federal trial where Bob Fitzpatrick was finally able to tell the truth of what was going on in the Boston office of the FBI and headquarters in Washington for the first time, and it was stunning. I knew this story had it all, but most importantly it had a brave and courageous hero who’d risen from nothing as a boy to achieve his dream only to have it turn into a nightmare.
Douglas Cobb: Also, Jon, I’m sure that you had an opinion about Whitey Bulger before you ever began working on the book. What was it? Did it change by the time you and Robert finished writing the book?
Jon Land: Bulger was just another name in the news for me before BETRAYAL. By the time we finished writing the book, I knew he was a monster, a psychopath, and a cunning manipulator who had no boundaries. There wasn’t anything he ever did for anyone without expecting something back in return. And his arrogance was incredible; he believed he could get away with anything and, in large part, he was right because the FBI was protecting him. It remains amazing to me, even more so now with the trial getting underway, that Fitz told officials right up to the director’s office in Washington exactly what was going on—I mean, it’s not like they didn’t know—and yet they did nothing. They turned a blind eye and a deaf ear while Bulger went on murdering people and running a criminal enterprise, the Winter Hill Gang, that was even bigger than the guys they were trying to get in the Italian mob.
Douglas Cobb: You and Robert Fitzpatrick don’t live in the same state, right? This question can be for both of you.
What were the logistical problems, if any, writing Betrayal, and who did what as you wrote it?
Jon Land: I was fortunate in the respect that Bob had already penned lots of pages and chapters. Now, let me put this kindly, they weren’t exactly publishable. So my job was to sort through them and assemble them into a coherent neighborhood. In conjunction with that, Fitz and I met and spoke frequently to review my work and further delve into the complexities of the story. Because that was the biggest challenge: making sense of a tale so intricate that an intricate understanding of it had defied other writers for years. I think that’s what BETRAYAL does better than anything else. You come away from reading the book knowing the chronology of events and exactly who was responsible for what when. In large part, that’s because it’s the only book on the whole sordid era written by someone—Fitz—who was actually there and lived it, from the inside out instead of the outside in. Beyond that, my job was to find Fitz’s voice. His cadence, his tone, his word choice. This book had to tell his story in his words. In that respect the book almost reads like fiction and that’s why it’s so hard to put down.
Robert Fitzpatrick: (laughs) We met for lunch and I handed Jon, what?, a suitcase full of chapters I’d written, so his recollection is generally correct. As I recall, there was a lot of back and forth where we’d talk so I could clarify material he’d either read of mine or researched independently. It was like a jigsaw puzzle, our biggest challenge being to fit all the pieces together. Because that was thing—nobody had ever made sense of the whole episode before. It’s so complex, even convoluted, with so many names and so many players. We were trying to create a program so people who read the book would finaly be able to get the whole thing straight
Douglas Cobb: Jon/Robert, do you think that you will watch the trial? Do you think there are any surprises in store for the American public, especially when it comes to certain deals that FBI agents sometimes make between each other?
Jon: I’m going to be honest with you here. My interest in the trial only pertains to how Fitz is treated when he testifies and what the whole process does for book sales (chuckles). Our great book is getting a new life and a second look because of the trial and if any book ever deserved to be a big bestseller, it’s BETRAYAL, and nobody deserved that attention and recognition more than Fitz. He sacrificed his brilliant career to do what was right in going after Bulger and the FBI vilified him as a result. So, in a lot of ways, this trial isn’t just about being Bulger to justice, it’s about justice for Bob Fitzpatrick. Because what you’re going to hear in the coming months will reveal how so much of this could have been avoided if the FBI had just listened to their own man and done what Fitz told them: close Bulger as an informant who wasn’t giving them anything of substance and target him as the criminal he was instead.
Robert Fitzpatrick: I’ll be testifying as an expert witness in the trial, as I have at others, especially the McIntyre trial which one of the cases where the FBI and DOJ [Department of Justice] was found to be complicit in the murder of an informant named John McIntyre I was involved with who was ready to give up Bulger, and ordered to pay damages in the millions of dollars to his estate. Interestingly enough, I’ll be testifying for the defense—kind of the ultimate irony, given my history with Bulger. But I don’t look at it that way, that I’m testifying for either side. I’m testifying to the truth, to what really happened and who was really responsible. Bulger’s a bad guy, a really bad guy—let’s get that straight. I mean he was the head of a criminal enterprise, the Winter Hill Gang, the whole time he was serving as an informant for the Bureau. But what allowed Bulger to be was the fact that he was protected not just by a few rogue agents but my direct superior, the head of the Boston office, and his superiors at headquarters in Washington that included some of the most important officials in the building. Here’s the thing, Doug, when you tell the truth, you never have to remember what you said and I intend to just tell the truth when I testify.
Douglas Cobb: Robert, when did you first hear about Whitey Bulger and his criminal organization, the Winter Hill gang (I think that’s what it was called–though, I may have that incorrect), and under what circumstances?
Robert Fitzpatrick: When I was a supervisor and instructor down at Quantico. I taught, among other courses, a major “death investigation” seminar for the National Academy of Law Enforcement Officers. One class included the colonel in charge of the Massachusetts State Police who shared with the class the fact that in Boston an FBI Top Echelon (TE) informant named Richie Castucci had been killed and the colonel suspected the FBI was to blame. You can imagine how shocked I was at hearing that. Later, when I was transferred to Boston, I learned that murder and other incidents were rooted in a culture of corruption that was festering through the FBI’s office there thanks in large part to the office’s insistence, and Washington’s I’d later learn, of keeping Bulger open as an informant even though he wasn’t providing any worthwhile intelligence or information. I didn’t write my report recommending he be closed as an informant and targeted as a criminal until I interviewed him personally to confirm my suspicions.
Douglas Cobb: How influential was Whitey Bulger and the Winter Hill Gang on the Boston crime scene, and that of Massachusetts? How many murders do you believe they were responsible for committing?
Robert Fitzpatrick: Bulger himself was alleged to have been responsible for 43 murders. Now what you’ve got to understand about Boston at the time was that you had two independent, essentially competing criminal enterprises in the Winter Hill Gang and the Italian mob. The FBI’s singular purpose at the time was to get the Italian mob through any means necessary, which explains why they brought Bulger on as an informant in the first place so he could help bring down, essentially, a rival gang. And that’s the key point since, as the Italian mob’s power eroded, his and that of his Winter Hill Gang expanded. So in essence the FBI was aiding and abetting Bulger’s power by eliminating his competition. As a footnote, when I arrested Boston mob boss Jerry Angiulo, I did it with no help or intelligence from Bulger whatsoever.
Douglas Cobb: What do you think, Robert, are some of the reasons that it took so long to finally catch Bulger and bring him to justice?
Robert Fitzpatrick: Well, first he had been planning his escape for some time and had plenty of cash on hand to fuel his efforts. But there’s also the possibility that both DOJ and the FBI didn’t want him to be caught, precisely because the specifics about their mishandling of him as informant are now going to come out at trial. I have heard it reported that a number of tips as to Bulger’s whereabouts were ignored, including several about him when he moved to Santa Monica. The tipping point came when fugitive apprehension was taken out of the FBI’s hands and given to the Federal Marshall’s Service. At that point, the Bureau could no longer cover their tracks, if in fact they were turning a blind eye to his potential whereabouts. But there’s no doubt in my mind they would’ve been a lot happier if he’d stayed on the lam and never got the chance to tell the story he’s going to tell now.
Douglas Cobb: What were the years between which Whitey maintained his criminal organization?
Robert Fitzpatrick: My recollection is he took over the Winter Hill Gang and continued to run it even after Howie Winter was released from prison. I left the Bureau in 1986 and I can tell you with certainty that Bulger ran the gang for the whole six or so years I was in Boston and continued to do so for several years afterwards, until he disappeared in 1995. And, remember, FBI regulations prohibit using the head of a criminal enterprise as an informant, so by employing Bulger in that capacity they were clearly breaking their own rules—something else that went ignored.
Douglas Cobb: How did certain FBI agents interfere with the case, and why? Is their interference why you call the book Betrayal?
Robert Fitzpatrick: We called the book BETRAYAL because that’s the dominant theme; the betrayal of not only me, the agent they’d sent to put the Boston office on the straight and narrow, but also the entire country since by enabling Bulger to basically kill and commit crimes at will, the Bureau was betraying a sacred public trust. And it wasn’t just the Bureau. It was the Organized Crime Strike Force under Jeremiah O’Sullivan. It was the U.S. Attorney’s Office under future Massachusetts governor William Weld. In Washington, it was Sean McWeeney, John Otto and Oliver Ravell. A culture of corruption is what allowed Bulger to be and in allowing that to happen, the FBI betrayed each and every one of us.
Douglas Cobb: Robert, while you worked on the case, did you ever at any time feel like you were in danger or that your life was threatened in any way?
Robert Fitzpatrick: In retrospect, yes, because I’d become so much of a thorn in the Bureau’s side, I guess maybe they would’ve let Bulger target me the way he’d targeted the three informants I’d turned who were ready to give him up. But I think from the time we met for the first time Bulger knew better than to try. He was a street kid from south Boston, I was a street kid from Hell’s Kitchen. He had a rep and I had a rep, so maybe he knew better than to take me on that way. And he probably figured he didn’t need to because he had plenty of higher-ups in his pocket already. Bulger was a supreme egotist, never thought he could be touched by me or anyone else.
Douglas Cobb: Robert, have you been asked to testify in the Whitey Bulger case? Also, with Bulger’s capture, have you seen sales of Betrayal increase yet?
Robert Fitzpatrick: As I said before, I’ll be testifying for the defense but to the truth. And I wait for Jon to tell me about how the book is selling (laughs).
Douglas Cobb: This is the final question, Robert. Could you tell our readers briefly how Whitey was finally captured?
Robert Fitzpatrick: I believe a tourist visiting Santa Monica, California from Iceland called in a tip. Ironic, isn’t it, that one of the most notorious gangsters in American history got nabbed because of a foreigner.
Douglas Cobb: I thank you both for taking the time out of your busy schedules to let me have this exclusive look into the Whitey Bulger case. Also, thanks, Robert, for your service to the United States of America, and to always pursuing the truth, no matter where that might take you.
Written by: Douglas Cobb