Criticism & Features


NBCC Nonfiction Finalists Kevin Cullen and Shelley Murphy in Conversation with Ari Spool


Thanks to The School of Writing at The New School, as well as the tireless efforts of their students and faculty, we are able to provide interviews with each of the NBCC Awards Finalists for the publishing year 2013 in our 30 Books 2013 series.

Ari Spool, on behalf of the School of Writing at The New School and the NBCC, interviewed Kevin Cullen and Shelley Murphy, about their book Whitey Bulger: America's Most Wanted Gangster and the Manhunt That Brought Him to Justice (Norton), which is among the final five selections, in the category of Nonfiction, for the 2013 NBCC awards.

As I read Whitey Bulger: America's Most Wanted Gangster and the Manhunt That Brought Him to Justice, I kept having flashbacks. Every new name or location would summon a memory. At the book's first mention of Bulger's partner, Steve “The Rifleman” Flemmi, I remembered watching TV with my family during Flemmi's perp walk on the evening news. When Kevin Weeks entered the book's plot, I remembered the video of him leading the police to the beach where he, Bulger, and Flemmi had buried the bodies of many of the people they'd killed throughout Bulger's thirty-year career as a criminal.

Since I was so young, my memories of Whitey Bulger and his escape from justice are paired with the other scandals of the 1990s. I found myself thinking about the Big Dig, another thirty-year Boston saga,  which sank a highway called the Central Artery below the city itself.  I also remembered Tonya Harding's attack on Nancy Kerrigan, a native North Shore gal, and found myself unable to separate all the strands of these events. This book effectively straightened out these childhood recollections, but if anything, Bulger's mythology became even stronger. Bulger's history, before his famous escape from capture and subsequent on-the-lam lifestyle, is chock full of strange facts—he's like the Forrest Gump of twentieth Century Gangsters.

Born in the 1930s in Southie (South Boston), Bulger quickly became a delinquent. An early stint in prison first enrolled him in medical trials for LSD, which he claims gave him recurring nightmares for life; subsequently, he was placed in Alcatraz during the famous federal prison's heyday (Bulger claimed the food was better than other prisons). The 1970s found him back in Boston, lighting John F. Kennedy's childhood home on fire to protest mandatory school busing. He grew his own team of local hoods through cunning and killing. In the 1980s, the decline of the Italian mafia allowed Bulger to take a chunk of the profits on every ounce of cocaine that flooded his territory in South Boston, and sent him to Ireland to support the IRA in their efforts. A failed trans-Atlantic gunrunning attempt to those rebels was the beginning of his downfall—once he expanded outside of Boston, it was more difficult for the FBI agents who enabled his flagrancy to keep him out of the news.

Kevin Cullen and Shelley Murphy, two Boston reporters who followed Bulger's history as he made it, allowed me to ask them about both the mythology and the facts.

Ari Spool: You were able to conduct interviews with some of the people closest to Whitey Bulger, but not with Bulger himself. Do you think he's read your book? It seems quite probable, considering that, as you mention, he's read all of the other books about himself. What do you think his response to your reporting would be?

Kevin Cullen: We were told by investigators that Whitey and his brother Bill spoke in conversations recorded at the jail where Whitey was held prior to and during his trial very specifically about our book. At one point Whitey was considering talking to us for the book because, after he ignored several letters we wrote asking for him to cooperate, or at least read our manuscript for accuracy, I sent him a very specific letter asking to talk only about the Irish and IRA-related information in the book. I figured that might play to Whitey's pride in being involved in IRA activity. And he almost bit. But we were told Billy talked him out of it. Billy also declined to cooperate with our book.

Shelley Murphy: I believe Whitey has read our book. The day after it was released, he penned an indignant letter to an old friend, berating him for sharing letters with us that Whitey had written from jail after his capture in 2011. The friend shared the letters because they offered great insight into what Whitey thinks of himself and others.

Kevin Cullen: I'm sure Whitey read the book because he is a narcissist and reads everything about himself. I'm sure he would not like the unflattering things written about him, but so much of the book is based on well-established evidence and testimony. When it comes to Whitey, however, he claims everybody lies and he is the only one who tells the truth, but always in self-serving ways.

Shelley Murphy: He is desperate to convince people that he was never an informant and did not kill the two women he was accused of slaying, because he wants to convince people that he was a good bad guy, a gangster with scruples. He hates our book because we offer a true and honest portrait of him, with rich details from people who knew him intimately. He hates that we have read his letters, and spent hours interviewing his closest friends.

He has actually told his lawyer that he only killed people who deserved it and were part of the gangster life. Our book humanizes those victims, while simultaneously humanizing Whitey. After Whitey was sentenced to two life prison terms, one of his lawyers told a group of criminal defense lawyers in Boston that “Jim” had a murderous hatred of Kevin Cullen and demonstrated how he wanted to choke him to death. He tried to keep us from covering his trial by placing us on the defense witness list, then urging the court to exclude all witnesses. He once boasted to a friend that he wouldn't respond to our letters because that would make us important. In Whitey's mind, you are only important if he says so.

Kevin Cullen: The jury has spoken about his crimes, though I believe the crimes he was not convicted of were the result of uncorroborated testimony of other killers, most notably Steve Flemmi and John Martorano.

Shelley and I did a forensic examination of the jury's findings, based in part on interviews with a number of jurors, and they did not feel comfortable convicting him on the sole word of one or the other of Whitey's accomplices, even though they were under no illusions about his innocence in any of this.

He has always been good at sophistry and convincing people he is a man of principle, so he maintains because he never testified against anyone and nothing he provided to the FBI led to an indictment, he is not an informant.

Like everything with Whitey, that is a highly selective view.

Ari Spool: You reported on this story for an incredibly long length of time. What first tipped you off to Whitey Bulger's story, and why did you stay on the beat? How did you form close enough relationships with associates like Kevin Weeks, John Connolly, and Pat Nee (people who may not have been so excited to talk to reporters) to the point where they would consent to give you so many crisp details?

Kevin Cullen: My mother grew up in South Boston and my entire maternal side is still there. I spent a lot of time there as a kid, visiting my aunt and staying at her house a lot in the summer, hanging with my cousins. So I knew the town well even before I became a reporter. But when I arrived at the Boston Herald as the crime reporter in 1983, I struck up a source relationship with John Connolly, then a prominent agent in Boston's FBI office. Connolly trusted me because he knew my family was from Southie, and he went to Boston College around the same time as my cousin John Cunniff, an All-American hockey player, maybe the best player to come out of Southie. They were friends.

Shelley Murphy: I had heard of Whitey, the gangster, when I was a teenager. I grew up in Savin Hill, a Dorchester neighborhood that borders South Boston and I attended South Boston High School. Some of Whitey's victims were gunned down in my neighborhood in the 1970s, and there were whispers even then that he had killed them.

Kevin Cullen: After the FBI arrested the Mafia leadership in September 1983, I began looking at who was the biggest criminal in Boston, and the answer was always the same: Whitey Bulger. My State Police, DEA, and Boston Police sources told me that they had been trying to nail Whitey and his partner, Steve Flemmi, but they suspected the FBI was protecting Whitey.

Connolly would pick me up in his car and we'd drive around Southie, or downtown, together, but whenever I’d ask him about Whitey and Stevie, he’d steer the conversation away. It made me suspicious. And then Connolly was always talking about how great a guy Bill Bulger was, that he was smart enough to be president, but that he was punished for being principled and standing up against busing.

Shelley Murphy: As a reporter, I started focusing on Whitey in 1985 when his name was mentioned during Boston's first big Mafia trial. A Boston Mafioso boasted during an FBI-bugged conversation that Whitey, leader of the so-called Irish Mob, would kill people at the Mafia's request. Over the next several decades, I covered organized crime—writing stories about the Irish, the Italians, IRA-gunrunning, drug trafficking, FBI corruption, and gangland murders. I covered every twist and turn of the Whitey saga—the criminal cases against his associates, the wrongful death suits, the international manhunt.

Kevin Cullen: At some point, my State Police sources were more specific in their complaints: they said that the FBI had compromised their investigation into Whitey and Stevie. When I confronted Connolly with that allegation, he said the Staties were incompetent and needed someone to blame for their own fuck ups. But I kept hearing it too many times and places and I eventually came to the conclusion that the only explanation for Whitey's charmed life was that he was an FBI informant, because I knew the FBI didn't target its own informants. In 1988, I went to Globe editor Jack Driscoll with my suspicions and he decided it was worth commissioning a lengthy investigation by the Spotlight Team, the Globe's investigative team. I was assigned to the Team with Gerry O'Neill, as editor, and Dick Lehr and Chris Chinlund as reporters. We were able to confirm that Whitey was an FBI informant, but in the process of reporting that, the FBI caught wind of what we were up to and an agent named Tom Daly called me at the Globe and said I'd be murdered if we wrote that Whitey was an FBI informant.

Shelley Murphy: I was there when investigators dug up secret graves. I got to know all of the players connected to the story, on both sides of the law. John Connolly, Pat Nee, Kevin Weeks, and many others spoke to me because they respected me. They might not always like what I wrote, but they knew it would be fair and accurate.

Kevin Cullen: One of the reasons I felt so strongly about staying on the Whitey story is the idea that a federal agent would threaten me and, by extension, my wife for exposing the truth. My wife and I lived in Southie at the time and were extremely vulnerable. One of the things I struggled with in going forward with this story, especially exposing Whitey as an informant, is that I was fond of Connolly, and he was friendly with some of my cousins. I also worried that Whitey would be murdered by other criminals, but he told his FBI handlers that the other criminals wouldn’t believe the Globe story. And he was right.

Pat Nee and I always got along, even though I knew he was a criminal and was under no illusions about what he was capable of. Frankly, Pat liked my reporting from Northern Ireland. Unlike Whitey, who exaggerated his connections to the IRA, Pat was very seriously involved in the IRA. He and I knew an awful lot of people in Northern Ireland, so we shared that, and Pat told me he was appreciative of the fact that I stayed on the FBI about Whitey being an informant. Kevin Weeks said the same thing, though I think Kevin really disliked me before Shelley stuck up for me and told Kevin that I wasn't a bad guy.

Kevin [Weeks] wrote in his book that I was so afraid of them that I “ran away” to England. I called him up and said that my moving to London came ten years after the threat to my life, and that in my business, getting posted to London is called a promotion. Kevin fixed that in his paperback.

One final reason I stayed on Whitey is because I so deeply resented the myth, propagated by his brother Bill and other apologists, that Whitey had nothing to do with drugs. I wrote the first stories about Whitey getting a cut of everything that moved in Southie, and Bill Bulger approached me specifically to complain that I was maligning his brother and by extension his family. I had cousins from Southie who died of drug abuse and it really bothered me the cult of silence that surrounded that issue in the years that Whitey was king of Southie. Perhaps the greatest satisfaction I took from Whitey's trial was his admission that he made millions from the drug racket.

Ari Spool: The story of Whitey Bulger is a story of an entire ecosystem of Boston patriarchy. Do you think that any of these types of attitudes remain in Boston? Or do you believe, as Judge Denise Casper told Bulger at his sentencing, “You, sir, do not represent this city.”

Kevin Cullen: Boston is still very patriarchal, with few women in positions of power. But I think Whitey's Boston is long gone and hard to find. That said, the FBI would create another Whitey if they could, and they routinely do, though never on the same scale as Whitey. A couple of years ago, I wrote a series of columns on a mini-Bulger, a Mafia guy named Mark Rossetti who is suspected in a half dozen murders but was protected by the FBI as an informant. But I think that Whitey was a product of a certain time and place in Boston that has passed. He would not have been released from prison if his brother wasn't so politically connected. He rose quickly in the underworld because of gang wars that took out competitors, and those gangs don’t exist to the same extent, and organized crime's real moneymaker, the number, has been taken over by the government. Basically, all the gangs have left is sports book and drugs, and the latter is rife with so much risk. Whitey could only be protected under the guise of being used to get a bigger threat: the Mafia. But the Mafia is a shell of itself. And the patronage that his brother used to create a healthy stable of apologists/sycophants has been destroyed by anti-corruption laws and ethics commissions. Whitey could only exist with Billy and Billy's political world has been almost totally neutered.

Bottom line, Whitey could only make the money he wanted to make by being a drug dealer today. Of course, he was a drug dealer, but back in the day he had the cover of the other rackets to use as his beard. Those other rackets are gone.

Shelley Murphy: I agree with Kevin Cullen when he says Whitey was a product of a particular place and time. Boston is not the same. South Boston is not the same. Whitey has been exposed as a master manipulator who cultivated a Robin Hood image while making millions from drugs that he pumped into his own neighborhood.

Ari Spool: As a native of the Boston area, my 1990s childhood was dominated by two news stories: that of Whitey Bulger and his associates and that of the Big Dig. To me, they always bore a connection—unwilling burial. Do you think that these stories altered the collective psyche of the Hub? If so, how?

Kevin Cullen: I never really looked at it that way. I think Boston is a much better looking city without the Central Artery, and it's brought the waterfront more into play with the rest of the city. So there is that similarity: the ugliness was buried, like Whitey's victims. The price tags are similar too. At $15 billion, the Big Dig was the most expensive public works project in US history. I don’t think we can toll up the cost, both monetary and human misery, when it comes to the federal government's protection of Whitey and their desecration of the victims and the victims' families.

One of the things Shelley and I felt strongly about doing, and really focused on it, was explaining that the corruption of the FBI and Justice Department went well beyond enabling Whitey to murder with impunity. It was, after this scandal was exposed, the Justice Department continuing to libel and smear the dead and their loved ones. A few years ago, a Justice Department lawyer accused Patricia Donahue of being a racist, saying that's why she left for the suburbs with her three sons. They moved to the suburbs because Michael Donahue was murdered [by Whitey Bulger] with FBI connivance and they couldn't afford their house in Boston anymore. In trying to avoid paying the family of Debbie Hussey any money for her murder, a different Justice Department lawyer referred to her as the girlfriend of Steve Flemmi. Actually, she was Flemmi's stepdaughter and sex toy.

He raped her from the time she was thirteen or fourteen, even as he slept with her mother. Flemmi is foul, but so is a government lawyer who would smear a dead girl.

Bottom line, in getting back to your metaphor, Boston is a much more open city, in terms of confronting an ugly past, whether it's Whitey or racial intolerance. And it's a lot easier to get to the airport.


kevincullenKevin Cullen, a Pulitzer Prize-winning journalist who has written for the Boston Globe since 1985, was the first to raise questions about Whitey Bulger's relationship with the FBI. A frequent commentator on NPR and the BBC, Cullen has won major journalism prizes including the Goldsmith Prize, the George Polk Award, and the Selden Ring Award.


Shelly-MurphyShelley Murphy has covered Whitey Bulger and organized crime in Boston since 1985, beginning at the Boston Herald and moving to the Globe in 1993. She has won a George Polk Award for National Reporting.



Ari Spool is the Mayor of New York City. In the past she's written for Interview, The Stranger, and BOMB Magazines, and was the managing editor of Impose Magazine and 'SUP Magazine. She is currently a scholar in the Riggio Program for Writing and Democracy and concurrently pursuing her MA in Media Studies at the New School.