By Kevin Cullen and Shelley Murphy
He sat in the back of a black SUV wearing blue jeans, handcuffs, and a scowl. After sixteen years on the run, Whitey Bulger had returned to the South Boston waterfront, to a town that had changed so much that he stared uncomprehendingly out the window. He no longer really belonged in this place, where once he had wielded such power, and nothing about it now belonged to him. The city’s history had outrun him, even as his own had caught up with him.
The case against Whitey had originated in the old downtown courthouse named for John McCormack, the US Speaker of the House who was instrumental in building the South Boston housing project where Whitey grew up. Now he was on his way to the new federal courthouse on the Southie waterfront named for one of his neighbors from that housing project, Joseph Moakley, the longtime congressman. When he was a young bank robber, driving an Oldsmobile convertible at a time when hardly anyone in the neighborhood could afford a car, Whitey would pull over if he saw Moakley’s mother walking home with groceries and give her a lift.
It was a small world, Whitey’s world.
The courthouse was just up the street from the spot where, in 1982, Whitey used a rifle to kill a hoodlum named Brian Halloran who had tried to turn him in to the Federal Bureau of Investigation (FBI). Halloran had stumbled into the crosshairs because he didn’t know that the FBI was willing to let him die to protect their secret, that Whitey was their informant. An innocent man, a truck driver named Michael Donahue, had also fallen that day, killed by the same spray of bullets—and now his family was waiting inside the courthouse, waiting to lay eyes on the man who had ripped hope from their lives twenty-nine years before.
The faded, peeling waterfront where Whitey Bulger gunned down those two men was long gone, replaced while he was on the lam by sprawling restaurants, gleaming bars, and high-rise hotels that cater to the young and the moneyed, the new Bostonians for whom the name Bulger means little or nothing. As he eyed this shiny new section of town, Whitey said a few words to his guards about the stunning transformation, about the new Boston he didn’t know.
As the SUV pulled into the courthouse’s underground garage, a Coast Guard boat idled in Boston Harbor, behind the courthouse, an officer manning a machine gun mounted on deck, an almost ludicrous show of force. The idea that anyone would mount a daring or suicidal operation to kill or spring Whitey was preposterous. Sixty-five when he fled, Whitey was eighty-one years old now, and everybody had turned on him—everybody except his girlfriend, Cathy Greig; his immediate family; and John Connolly, the FBI agent who grew up with the Bulgers in the projects and then used his badge to protect the Bulger name. Greig, who had been captured along with Whitey in Santa Monica, was in custody in the courthouse, too. Connolly was also locked up, doing forty years in Florida for helping Whitey kill a potential witness, someone who could have exposed Whitey’s Faustian partnership with the FBI decades earlier. Whitey’s younger brother Bill was a few miles away, getting ready to leave his South Boston home for the short drive to the courthouse.
Whitey rode the elevator to the fifth floor, surrounded by deputy US Marshals who kept their sunglasses on indoors. As he waited in an anteroom for his case to be called, Michael Donahue’s widow, Patricia, sat in Courtroom 10 with her three sons, Michael Jr., Shawn, and Tommy, who had grown up without a father. The special agent in charge of the FBI in Boston walked in and took an empty seat on the right side of the gallery, directly in front of the Donahues, but said nothing to them. He didn’t know them, or any of the families of Whitey’s victims, who sat clustered together.
When Whitey shuffled into the courtroom, he quickly spotted his brother Bill out in the spectators’ gallery and mouthed a cheerful hello even before he made it to the defendant’s table. For many years one of the most powerful politicians in Massachusetts, Bill smiled and nodded back.
Whitey’s $822,198 in cash, hidden in the wall of his apartment in Santa Monica, was of no use to him now. The thirty guns hidden in those same walls proved useless, relics of a time when he’d always had a gun within easy reach. There had been no defiant, bloody standoff with the law before his arrest, a drama that would have better served his legend. His years of gunplay behind him, the old man had surrendered quietly and almost with a smile. The Whitey Bulger standing there in the courtroom, in his ill-fitting blue jeans, white smock, and sneakers, looked like any other casually dressed octogenarian or a Southern California retiree, which is what he had been just a few days before.
Over the next few weeks, there would be more court appearances as the feds tried to figure out what to do with him. Each time, the black SUV drove him up the Southeast Expressway, the main road into Boston, taking him past some of the spots where he had buried his secrets. To the right, next to a railway bridge over the Neponset River, were the soggy graves of Debra Davis and Tommy King. A little farther up, under the sand at Tenean Beach, there was Paulie McGonagle’s. Off to the left of the highway, beneath some mounds of dirt across from the firefighters’ hall, there was the oversize makeshift grave that held Deborah Hussey and Bucky Barrett and John McIntyre. They were just six of the nineteen people Whitey was charged with killing.
Whitey hid the bodies to lessen the risk of prosecution. It’s never good business to leave a corpse behind: no body, no case. But he also did it to preserve his image in the Town, as South Boston natives call their neighborhood. It was especially important to Whitey that his role in the demise of the two women remain hidden. He was a criminal, he would readily admit, but he was an honorable criminal. Gangsters with scruples don’t kill women, and Whitey insists to this day that he did not kill Debra Davis or Deborah Hussey. He says the last years of his life will be spent clearing his name, not just in the killing of the women but in this whole matter of his being an FBI informant. “I never put one person in prison in my life,” he claimed in a letter to a friend.
This is the illusion Whitey lived by and where his legend as the good bad guy began. He will most likely die in prison, no matter how he plays his final hand. Nothing seems more certain to die there with him than that legend.
There have been other books written about Whitey Bulger, many of them told through the eyes of people who worked for him or pretended to. Other, more serious accounts were written when knowledge of Whitey was limited or, in some cases, incomplete or incorrect. This book aims to provide the first complete and authoritative accounting of this man, of his rise, reign, and final reckoning. We aim, in short, to present Whitey in full. Many descriptions of him, and much of the lore about him, have traded in caricature, making him a two-dimensional figure more monstrous than human, if you hate him, more human than monster, if you don’t. Whitey was more complicated, more compelling, more frightening than that.
In the sixteen years that he was on the run, Whitey’s place in the public consciousness seemed to grow less, not more, nuanced. Popular culture cluttered public perception, as it evolved in his absence. Myth overgrew reality. Frank Costello, the venal, scheming Southie mob boss played by Jack Nicholson in Martin Scorsese’s film The Departed, was loosely based on Whitey. Costello was a sociopath, devoid of conscience or redeeming values, with blood literally dripping from his hands. Nicholson’s captivating and brilliant portrayal didn’t really capture the man it was modeled on. Others painted with an even broader brush. One former criminal associate wrote a book describing Whitey as a closet homosexual who once had a liaison with the actor Sal Mineo. The FBI, which used and protected him for decades, suddenly described the fugitive Whitey as a pervert who had sex with girls as young as twelve. After he disappeared, Whitey’s portrayal evolved from that of a cunning criminal to a sleaze.
A closer inspection of Whitey’s life reveals a more intriguing character, a strange and complex amalgam of the depraved and the blandly conventional. If Whitey spent his youth running away from the warmth and stability of his family home, he spent much of his adult life trying to re-create something he saw as a traditional, nurturing domestic environment. That he did so while maintaining two separate households with two separate women is just one of the many incongruities that define him. Whitey saw no contradiction in slaughtering someone with a machine gun and then, an hour later, sitting down to dinner with one of his mistresses and her children. At those nightly family dinners, he insisted that no one answer the phone should it ring during the meal and lectured the kids on staying away from bad influences.
He considered himself more paternal than pathological, nothing like the other bad guys. Yes, he was a criminal, but to hear him tell it he only hurt those who threatened his business. Whitey, though, was expert at blurring that line. Two accomplished men assisted in this preening self-portrait: Bill Bulger, who could never fully face what a menace his brother was, and one of Bill’s protégés, FBI agent John Connolly. Connolly cast Whitey as an indispensable ally in the FBI’s war against the Mafia. The truth was otherwise; almost everything Whitey knew about the Mafia he gleaned from his partner, Steve Flemmi, who enjoyed similar protection from Connolly and the FBI. Connolly reaped the rewards of being one of the FBI’s top Mafia fighters, but his ulterior motive was to ensure that the Bulgers, the family he’d grown up with and which had helped him in his formative years, would not suffer the ignominy of seeing Whitey publicly accused of sordid crimes. To understand why Connolly would risk his career and ultimately his freedom to protect the good name of the Bulger family is to understand South Boston, whose residents valued loyalty to family, neighbors and neighborhood over all else. Like the waterfront Whitey came home to, that South Boston is largely gone today, a victim of demographics and time. It is the town Whitey looked for out the window of that black SUV but didn’t see.
If this book is the first comprehensive biography of Whitey Bulger, it is also a social history of a time in Boston when a life like Whitey’s was possible. It begins during Roosevelt’s New Deal, which brought the Bulgers to South Boston in the first place, and encompasses the years when the city’s working-class enclaves were still places where political loyalty ensured jobs and social mobility, the years when the Irish took full control of Boston’s politics and sought control of its criminal rackets, too. Whitey’s rise also embraced the divisive era of court-ordered integration of the city’s schools, when those working-class enclaves felt besieged as never before. Whitey joined that struggle, waging a symbolic, sometimes violent battle on behalf of Southie—a story this book tells for the first time. Whitey Bulger also encompasses the years during which ethnic divisions pitted Irish and Italian gangsters against each other, a fight the FBI joined on the side of the Irish, enabling Whitey’s rise and ultimate hegemony. Whitey, in fact, is facing criminal charges now only because a confederation of Massachusetts State Police, Boston police, and federal drug agents dared to challenge the FBI’s role as the nation’s, and the region’s, premier law enforcement agency.
And so, in his own bloody way, Whitey Bulger’s life was fused with the modern history of the city. During his career he became one of its most recognizable icons. Boston is the city of John Adams, John Kennedy, and Ted Williams, but there are few names better known or more deeply associated with the city than Bulger’s. Certainly he is Boston’s most infamous criminal. After his capture, he suggested to a friend that he might have now replaced Al Capone and Machine Gun Kelly as the most intriguing of Alcatraz’s former denizens. He might be right. And yet so much of what is known about him is crudely embellished or simply wrong.
We grounded our understanding of Whitey Bulger in our decades of covering his career as reporters for the Boston Globe and other Boston media, but not with any direct input from our subject or his family. Whitey Bulger refused to be interviewed by the authors. He ignored letters written by us to him in jail. Indeed, Whitey was more than uncooperative; he was outright hostile to this project, as he spelled out in letters to a friend from his Alcatraz years. Whitey will never forgive the Globe for the way it covered the court-ordered busing that desegregated Boston’s public schools and championed it on its editorial pages. Busing, he maintains, ruined South Boston. He has said he hates Shelley Murphy for writing stories about him and his brother Bill that were, in his view, hurtful to his family. He also considers her a traitor: Murphy grew up in Dorchester, attended South Boston High School, and was herself caught up in the busing crisis. She has also broken many of the most important stories about Whitey over the years. Kevin Cullen, part of the Globe team that outed Whitey as an FBI informant in 1988, was, Whitey said, “another lowlife…who has lied about my family and me.” Cullen lived in South Boston through much of Whitey’s reign, and many of his relatives still live there.
We believe Whitey saw a request for an interview for this book not as an attempt to get his side of the story but as a threat. “I hate the Globe,” he wrote to a friend. “Shelley, Cullen . . . they will twist my words and sensationalize it.” Despite his cynicism about our motives, we have sought to be fair to Whitey in this book, though of course there is no diminishing his crimes. We have tried, above all, to describe him in all his complexity.
The public record about Whitey has changed considerably, and deepened greatly, over the last decade, when the first books about Whitey Bulger appeared. The passage of time has made it easier to parse what is true and what isn’t. Many who once lived in fear of speaking publicly now open up about him. We grounded much of this book in the accounts of some of the principals in Whitey’s life, including some of his key criminal comrades. Their still vivid recollections help to flesh out long-ago scenes and dialogue. Also, some of those principals—Whitey’s criminal associates Steve Flemmi, John Martorano, Kevin Weeks—have testified repeatedly in court, making it possible to corroborate their claims in interviews with their sworn testimony. We have made every effort to verify their words and deeds, but there are times when they are the only source for what was said or done. Their recollections are detailed—almost photographic, in many cases—and they ring true, or we wouldn’t have used them. But the reader, like the authors, should bear in mind that these are what they are—recollections, from men, in some cases, with mixed motives. Others—including Weeks; Patrick Nee, one of Whitey’s rivals turned associate; and Teresa Stanley, Whitey’s girlfriend of thirty years—gave multiple interviews to the authors. Richard Sunday, Whitey’s prison friend, gave the authors many interviews and access to a series of letters Whitey sent him after his June 2011 arrest, which serve as a window into Whitey’s own version of his story and his thinking.
But the bulk of the book is based on the authors’ long and detailed knowledge of Whitey Bulger, the fruit of more than twenty-five years of reporting on his exploits, interviewing the FBI agents who protected him, the criminals who worked with him, the lawmen who hunted him down, and the families he destroyed. We have covered dozens of hearings and trials, from Boston to Miami to Los Angeles, and followed his story from Massachusetts to Florida to Ireland to Louisiana to California to Iceland. It is an account made richer by interviews with some of those who spent time in prison with Whitey and by the examination of thousands of pages from his prison file. It is a story bolstered by interviews with those whom Whitey and Catherine Greig met and befriended during their sixteen years on the run, from the bayous of Louisiana to a modest apartment complex a few blocks from the beach in Santa Monica. And it is a story underwritten by the institutional authority of the Boston Globe, which first exposed Whitey’s deal with the FBI and has driven understanding of the narrative of his life ever since.
More than anything, this book tries to capture the contradictions that fill in the silhouette that is Whitey Bulger—a man who considered himself a patriot even as he used murder and the threat of it to amass a fortune, a man who could fall asleep moments after killing someone but couldn’t watch a sick dog be put down, a man who held loyalty to be the highest moral value even as he traded damning information about friends to the FBI. There is great sweep and nuance to his story, but it is striking, in the end, how small Whitey’s world was, just a couple of miles, as the crow flies, from the soggy graves of Neponset to City Point, where Whitey regularly had dinner at the home of his politician brother. It is an epic tale with many characters, but one ultimately sketched on a very small canvas.
Shortly after his arrest in June 2011, Whitey was flown by Coast Guard helicopter from his jail cell in Plymouth, south of Boston, to the waterfront courthouse, giving him an aerial view of the shoreline. Those old graves had been dug up, the bodies exhumed, while Whitey hid in open view on the other side of the country. Now he was back in South Boston, his hometown, in chains, made to answer for those bodies and thirteen others. As he looked down from the helicopter, it may have dawned on him that he might still be in charge in his corner of this world if he had never stepped beyond those few square miles where all the shakedowns and killings were plotted and carried out, where Whitey first met his FBI handler, where, for all his misdeeds, he was embraced and not shunned by his brothers and sisters, his nieces and nephews, and his women.
Inside that narrow space, he was untouchable, protected by a tradition of neighborhood loyalty fostered on the stoops of that housing project in Southie, protected by the arrogance and corruption of an FBI and a Justice Department that tolerated murder as an acceptable price of doing effective law enforcement. His capture after a worldwide manhunt that was, by turns, intense and incurious, epic and inept, put the spotlight back on the life, the legends, the lies and the myths, on families protected and families ruined, on the neighborhood where loyalty was everything and where now, for him, it was nothing.
Reprinted from Whitey Bulger: America’s Most Wanted Gangster and the Manhunt That Brought Him to Justice by Kevin Cullen and Shelley Murphy. Copyright (c) 2013 by Globe Newspaper Company, Inc. With the permission of the publisher, W.W. Norton & Company. All rights reserved.