Black Mass

  Table of Contents

  Praise

  Title Page

  Dedication

  Prologue

  Introduction

  PART ONE

  CHAPTER ONE - 1975

  CHAPTER TWO - South Boston

  CHAPTER THREE - Hard Ball

  CHAPTER FOUR - Bob ’n’ Weave

  CHAPTER FIVE - Win, Place, and Show

  PART TWO

  CHAPTER SIX - Gang of Two?

  CHAPTER SEVEN - Betrayal

  CHAPTER EIGHT - Prince Street Hitman

  CHAPTER NINE - Fine Food, Fine Wine, Dirty Money

  CHAPTER TEN - Murder, Inc.

  CHAPTER ELEVEN - Bulgertown, USA

  CHAPTER TWELVE - The Bulger Myth

  CHAPTER THIRTEEN - Black Mass

  CHAPTER FOURTEEN - Shades of Whitey

  CHAPTER FIFTEEN - Connolly Talk

  CHAPTER SIXTEEN - Secrets Exposed

  PART THREE

  CHAPTER SEVENTEEN - Fred Wyshak

  CHAPTER EIGHTEEN - Heller’s Café

  CHAPTER NINETEEN - In for a Penny, in for a Pound

  CHAPTER TWENTY - The Party’s Over

  Epilogue

  Sources

  Notes

  Acknowledgements

  Index

  Copyright Page

  Praise for Black Mass

  “A parable of what happens when law enforcement officers get too close to their informers. It is a story that the FBI almost succeeded in suppressing. Black Mass should prompt a re-evaluation of the uses and misuses of informers by law enforcement officials throughout the country.”

  —Alan Dershowitz, author of Reversal of Fortune: Inside the Claus Von Bulow Case, The New York Times Book Review

  “This is a heartbreaking and enraging story of corruption and crime, but it has its heroes, especially Dick Lehr and Gerard O’Neill. These reporters were among the first to shine light on the shadowy collusion of heinous murderers and an FBI cut loose from its moral center. Now, with this powerful book, Lehr and O’Neill bring the whole story into the open. Black Mass is a work of rare lucidity, high drama, journalistic integrity, and plain courage.”

  —James Carroll, author of An American Requiem and Boston Globe columnist

  “More than an exposé on the abuses of power, Black Mass tells of the shameful betrayal of all things decent.... Lehr and O’Neill give us all the details with a journalistic precision that does not sacrifice the power of the story. After reading Black Mass, you might wonder if any of us really knows who are the good guys and who are the bad guys.”

  —Michael Patrick MacDonald, author of All Souls: A Family Story from Southie

  “What a marvelous read Black Mass is.”

  —Dominick Dunne, author of Justice: Crimes, Trials and Punishments

  “A jaw-dropping, true life tale of how two thugs corrupted the FBI ... a disturbing account of corruption, blind ambition, and official complicity in dark deeds.”

  —The Baltimore Sun

  “You don’t have to be a Mafia buff to enjoy and appreciate the story as told in Black Mass.... Black Mass is all about the nation’s premier law enforcement agency gone bad, with two or more of their own leading the way. . . . What makes Black Mass simply great is not the fantastic reporting and writing of the sordid story, but the way the two authors bring readers into the world of South Boston. The story reveals the parochial ‘clan’ attitude that prevails in the neighborhood where one’s word is higher measure of a man than his life’s accomplishments.... It is a great story, a great book, and a rare look at how deadly boyhood friendships in a neighborhood like ‘Southie’ can be.”

  —The Providence Journal

  “The book is a great read—it reels you in and holds you. O’Neill and Lehr have the remarkable ability to put you in the room and on the street where the action takes place. The dialogue is vital, gutsy, down and dirty.”

  —William Bratton, author of Turnaround: How America’s Top Cop Reversed the Crime Epidemic (with Peter Knobler), The Boston Globe

  “[Lehr and O’Neill] vividly capture the turbulent culture and conflicting loyalties of the Boston underworld.”

  —Library Journal

  “Black Mass is the hair-raising true story of the cozy and corrupt relationship between the FBI, Bulger, and his sidekick Steven the ‘Rifleman’ Flemmi ... an unholy alliance that shifted the balance of criminal power in Boston from the Italians to the Irish and left Bulger and Flemmi shielded from prosecution for two decades.... Lehr and O’Neill assemble a breathtaking account of corruption, crime, and gross legal negligence.”

  —The Legal Times

  “A triumph of investigative reporting, this full-bodied true-crime saga by two Boston Globe reporters is a cautionary tale about FBI corruption and the abuse of power.”

  —Publishers Weekly

  “An eye-opening true-crimer. . . . The authors offer a pile of evidence that (in South Boston at least) politics is all too local.”

  —Kirkus Reviews

  “Black Mass tells a story of abuse of power and betrayal by those sworn to protect the public and uphold the law. It leaves me wondering whether standard operating procedures and agent-informant relationships throughout the country should be reviewed.”

  —The Federal Lawyer

  “The corruption laid out by Lehr and O’Neill is pervasive and horrifying enough to make even the most inveterate cynic gag.”

  —The Boston Phoenix

  For my sons, Nick and Christian Lehr

  For my even keel wife Janet and my sons, Brian and Shane O’Neill

  Prologue

  ONE SUMMER DAY in 1948, a shy kid in short pants named John Connolly wandered into a corner drugstore with a couple of his pals. The boys were looking to check out the candy at the store on the outskirts of the Old Harbor housing project in South Boston, where they all lived.

  “There’s Whitey Bulger,” one of the boys whispered.

  The legendary Whitey Bulger: skinny, taut, and tough-looking, with the full head of lightning-blond hair that inspired cops to nickname him Whitey, even if he hated the name and preferred his real name, Jimmy. He was the phantom tough-guy teen who ran with the Shamrocks gang.

  Bulger caught the boys staring and impulsively offered to set up the bar with ice cream cones all around. Two boys eagerly named their flavors. But little John Connolly hesitated, heeding his mother’s instructions not to take anything from strangers. When Bulger asked him about his abstinence, the other boys giggled about his mother’s rule. Bulger then took charge. “Hey, kid, I’m no stranger,” he told Connolly. “Your mother and father are from Ireland. My mother and father are from Ireland. I’m no stranger.”

  Whitey asked again: What kind of cone you want?

  In a soft voice Connolly said vanilla. Bulger gladly hoisted the boy onto the counter to receive his treat.

  It was the first time John ever met Whitey. Many years later he would say the thrill of meeting Bulger by chance that day was “like meeting Ted Williams.”

  Introduction

  IN THE SPRING of 1988 we set out to write for the Boston Globe the story of two brothers, Jim “Whitey” Bulger and his younger brother, Billy. In a city with a history as long and rich as Boston’s, brimming with historical figures of all kinds, the Bulgers were living legends. Each was at the top of his game. Whitey, fifty-eight, was the city’s most powerful gangster, a reputed killer. Billy Bulger, fifty-four, was the most powerful politician in Massachusetts, the longest-serving president in the state senate’s 208-year history. Each possessed a reputation for cunning and ruthlessness, shared traits they exercised in their respective worlds.

  It was a quintessential Boston saga, a tale of two brothers who’d grown
up in a housing project in the most insular of Irish neighborhoods, South Boston—“Southie,” as it was often known. In their early years Whitey, the unruly firstborn, was frequently in court and never in high school. There were street fights and wild car chases, all of which had a kind of Hollywood flair. During the 1940s he’d driven a car onto the street-car tracks and raced through the old Broadway station as shocked passengers stared from the crowded platform. With a scally cap on his head and a blonde seated next to him, he waved and honked to the crowd. Then he was gone. His brother Billy set off in the opposite direction. He studied—history, the classics, and, lastly, the law. He entered politics.

  Both made news, but their life stories had never been assembled. So that spring we set out with two other Globe reporters to change all that. Christine Chinlund, whose interests lay in politics, focused on Billy Bulger. Kevin Cullen, the city’s best police reporter at that time, looked into Whitey. We swung between the two, with Lehr eventually working mostly with Cullen and O’Neill overseeing the whole affair. Even though we usually did investigative work, this project was seen as an in-depth biographical study of two of the city’s most colorful and beguiling brothers.

  We’d all decided that central to Whitey Bulger’s story was his so-called charmed life. To be sure, Whitey had once served nine years of hard time in federal prison, including a few years at Alcatraz, for a series of armed bank robberies back in the 1950s. But ever since his return to Boston in 1965 he’d never been arrested once, not even for a traffic infraction. Meanwhile, his climb through the ranks of the Boston underworld was relentless. From feared foot soldier in the Winter Hill gang, he’d risen to star status as the city’s most famous underworld boss. He had teamed up along the way with the killer Stevie “The Rifleman” Flemmi, and the conventional wisdom was that they were taking an uninterrupted underworld ride to fame and riches because of their ability to outfox investigators who tried to build cases against them.

  But by the late 1980s the cops, state troopers, and federal drug agents had a new theory about Bulger’s unblemished record. Sure, they said, the man is wily and extremely careful, but his Houdini-like elusiveness went beyond nature. To them, the fix was in. Bulger, they argued, was connected to the FBI, and the FBI had secretly provided him cover all these years. How else to explain the complete and utter failure of all their attempts to target him? But there was a catch to this theory: not one of these theorists could show us proof beyond a doubt.

  TO US, the idea seemed far-fetched, even self-serving.

  For Cullen, who lived in South Boston, it cut against everything then known about a gangster with a reputation as the ultimate stand-up guy, a crime boss who demanded total loyalty from his associates. It defied the culture of Bulger’s world, South Boston, and his heritage, Ireland. The Irish have long had a special hatred for informants. We’d seen, some of us more than once, the famous John Ford 1934 movie The Informer, with its timeless and unmatched portrayal of the horror and hate the Irish have for a snitch. More local was a South Boston wiretap that became a classic in the city’s annals of wiseguy patter. The secret recording captured one of Bulger’s own underlings talking to his girlfriend.

  “I hate fuckin’ rats,” John “Red” Shea complained. “They’re just as bad as rapists and fuckin’ child molesters.” And what would he do if he found an informant? “I’d tie him to a chair, okay? Then I’d take a baseball bat, and I’d take my best swing across his fuckin’ head. I’d watch his head come off his shoulders. Then I’d take a chainsaw and cut his fuckin’ toes off.

  “I’ll talk to you later, sweetheart.”

  This was Whitey’s world, where feelings about informants cut wide and deep, from the lowbrow to the high. Even brother Billy voiced a more refined version of Red Shea’s sentiments. In his 1996 memoir, he recalled the time when he and some boyhood chums were playing baseball and broke a streetlight. The kids were told they’d get the ball back once they identified the offender. None broke rank. “We loathed informers,” wrote Billy Bulger. “Our folklore bled with the names of informers who had sold out their brethren to hangmen and worse in the lands of our ancestors.”

  Since this was Whitey’s folklore too, the four of us back in 1988 were flat-out incredulous about the informant theory. We turned the idea over and inside out and decided, no way. The claim had to amount to nothing more than the wild and reckless flailings of embittered investigators who’d failed in their bid to bust Whitey Bulger. The idea of Bulger as informant seemed preposterous.

  But the notion nagged, an irresistible itch that stayed close to the surface. What if it were really true?

  The big news in Boston in 1988 was the presidential candidacy of Massachusetts Governor Michael Dukakis, but all during these months of presidential politics we grew more intrigued and committed to the Whitey story. So Cullen went back out. Lehr joined in. There were more interviews with the investigators who’d stalked Bulger and tried to build cases against him. The investigators painstakingly reviewed their case-work, all of which ended the same way: Bulger walked away, uncharged and unscathed, laughing over his shoulder. They talked about a certain FBI agent, John Connolly, who, like the Bulgers, had grown up in Southie. Connolly had been seen with Whitey.

  We wrote to the FBI in Boston and requested, under the Freedom of Information Act, intelligence files and material on Bulger. It was a formality; that the request was stonewalled came as no surprise. But we certainly could not write a story reporting that Bulger was an FBI informant. We had only the strong suspicions—but with no proof—of others in law enforcement. No confirmation was forthcoming from inside the FBI. The best we had, we decided, was a story about how Bulger had divided local law enforcement. It would be a piece about cop culture, with troopers and drug agents always coming up short and then hinting at their dark suspicions of the FBI. In a way, Bulger had divided and conquered; he’d won.

  THE BOSTON underworld and the interplay between investigators involved ghost stories, smoke and mirrors; the idea of Bulger as an informant still seemed unlikely to us. Nonetheless, we launched a final round of reporting to test what we’d learned on our FBI sources. The gist of that reporting is described in chapter 16 of this book. In the end we were indeed able to confirm, from within the FBI, that the unthinkable was true: Bulger was an informant for the FBI and had been so for years.

  The story in September 1988 was published to heated denials from local FBI officials. In Boston, FBI agents were used to playing the press, feeding information to reporters thankful for a scoop that, of course, made the FBI look good. In this context, it came as no surprise that the Boston FBI acted offended, betrayed. And many people accepted their denials; after all, who was more believable? The FBI, the stand-tall G-men who’d been getting good ink for taking down the Italian mob? Or a group of reporters whom the FBI portrayed as having an ax to grind? With the utter unlikeliness of Bulger being an informant and the sheer vehemence of the FBI denials, the story was seen as speculation, not the dark truth.

  Nearly a decade would pass before the FBI was required by court order to confirm what it had steadfastly denied for so long: that Bulger and Flemmi had in fact been informants, Bulger since 1975 and Flemmi since before that. The disclosures were made in 1997 at the outset of an unprecedented federal court examination of the corrupt ties between the FBI and Bulger and Flemmi. In 1998 ten months of sworn testimony and stacks of previously secret FBI files revealed a breathtaking pattern of wrongdoing: money passing hands between informants and agents; obstruction of justice and multiple leaks by the FBI to protect Bulger and Flemmi from investigations by other agencies; gift exchanges and extravagant dinners between agents and informants. Many of the agents’ remarks featured an unmistakable arrogance—as if they owned the city. It was easy to imagine the FBI and Bulger and Flemmi celebrating their secret, holding their wineglasses high and toasting their success in outwitting the state troopers, cops, and federal drug agents who’d tried to build a case against them, never real
izing the fix was in.

  OF COURSE, the Bulger case does not mark the first time trouble involving agents and their informants has exploded publicly for the FBI. In the mid-1980s a veteran agent in Miami admitted to taking $850,000 in bribes from his informant during a drug trafficking case. Better known is the affair involving Jackie Presser, the former Teamsters Union president, who served as an FBI informant for a decade before his death in July 1988. Presser’s handlers at the FBI were accused of lying to protect him from a 1986 indictment, and one FBI supervisor was eventually fired.

  But the Bulger scandal is worse than any other, a cautionary tale that is, most fundamentally, about the abuse of power that goes unchecked. The arrangement might have made sense in the beginning, as part of the FBI’s war cry against La Cosa Nostra (LCN). Partly with help from Bulger and, especially, from Flemmi, the top Mafia bosses were long gone by the 1990s, replaced by a lineup of forgettable benchwarmers with memorable nicknames. In sharp contrast, Bulger was the crime boss who, throughout the years, was the constant fixture in the underworld. Whitey was the household name, and he and Flemmi the varsity players.

  “Top echelon informant” means an informant who provides the FBI with firsthand secrets about high-level organized crime figures. FBI guidelines require that informants be closely monitored by FBI handlers. But what if the informant begins to “handle” the FBI agents? What if, instead of the FBI, the informant is mainly in charge, and the FBI calls him their “bad good guy”?

  What if the FBI takes down the informant’s enemies and the informant rises to the top of the underworld? What if the FBI protects the informant by tipping him off to investigations conducted by other police agencies?