Black Mass

Whitey Bulger, the FBI, and a Devil's Deal


By Dick Lehr

By Gerard O’Neill

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When the FBI turned an Irish mobster into an informant, they corrupted the entire judicial system and sanctioned the worst crime spree Boston has ever seen. This is the true story behind the major motion picture.

James “Whitey” Bulger became one of the most ruthless gangsters in US history, and all because of an unholy deal he made with a childhood friend. John Connolly a rising star in the Boston FBI office, offered Bulger protection in return for helping the Feds eliminate Boston’s Italian mafia. But no one offered Boston protection from Whitey Bulger, who, in a blizzard of gangland killings, took over the city’s drug trade. Whitey’s deal with Connolly’s FBI spiraled out of control to become the biggest informant scandal in FBI history.

Black Mass is a New York Times and Boston Globe bestseller, written by two former reporters who were on the case from the beginning. It is an epic story of violence, double-cross, and corruption at the center of which are the black hearts of two old friends whose lives unfolded in the darkness of permanent midnight.


Published in Great Britain in 2015 by Canongate Books Ltd, 14 High Street, Edinburgh EH1 1TE

This digital edition first published in 2015 by Canongate Books

Copyright © 2000, 2001, 2012 by Dick Lehr and Gerard O’Neill

First published in the United States of America in 2000 by Public Affairs, a member of the Perseus Book Group, 250 West 57th Street, Suite 1321, New York, NY 10107, USA

The moral rights of the authors have been asserted

British Library Cataloguing-in-Publication Data
A catalogue record for this book is available on
request from the British Library

ISBN 978 1 78211 623 3
eISBN 978 1 78211 625 7

Every effort has been made to trace copyright holders and obtain their permission for the use of copyright material. The publisher apologises for any errors or omissions and would be grateful to be notified of any corrections that should be incorporated in future reprints or editions of this book.

Photo credits: James J. “Whitey” Bulger Jr. / FBI photo; Stephen J. “the Rifleman” Flemmi / FBI photo; Former FBI agent John Connolly / Boston Globe Staff Photo by George Rizer; Donato “Danny” Angiulo . . . / FBI photo; An early arrest photo of Bulger / Boston Globe;Frank Salemme . . . / Boston Globe Staff Photo by John Tlumacki; Flemmi / FBI photo; Gennaro J. Angiulo . . . / Boston Globe Staff Photo by Jim Wilson; John Connolly Jr., . . . / Boston Globe Staff Photo by Ted Dully; Boston FBI agent . . . / FBI photo; John M. Morris . . . / Boston Globe Staff Photo by Tom Herde; Millionaire Roger Wheeler . . . / FBI photo; Edward Brian Halloran / Boston Police photo; South Boston Liquor Mart / Boston Globe Staff Photo by John Tlumacki; By 1984, Bulger . . . / Boston Globe Staff Photo by John Tlumacki; FBI wanted poster . . . / FBI web site; Bulger and Catherine Greig, 1988 / Boston Globe Staff Photo by John Tlumacki; James J. “Whitey” Bulger / FBI photo.

For my sons, Nick and Christian Lehr,
and my daughters, Holly and Dana Lehr

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

Cast of Characters


James J. “Whitey” Bulger

Stephen J. “The Rifleman” Flemmi

Nick Femia, enforcer

Kevin Weeks, enforcer and Bulger’s “surrogate son”

Kevin O’Neil, associate

Patrick Nee, associate

Joseph Yerardi, associate

George Kaufman, associate


includes Bulger gang members and:

Howard Winter, boss

John Martorano, hitman

William Barnoski, associate

James Sims, associate

Joseph McDonald, associate

Anthony Ciulla, horse-race fixer

Brian Halloran, associate


Gennaro J. “Jerry” Angiulo, underboss

Ilario “Larry” Zannino, capo de regime and consigliere

Donato “Danny” Angiulo, capo de regime

Francesco “Frankie” Angiulo, associate

Mikey Angiulo, associate

J. R. Russo, capo de regime

Vincent “The Animal” Ferrara, capo de regime

Bobby Carrozza, capo de regime

Frank “Cadillac Frank” Salemme, Flemmi’s boyhood pal and leading Mafia boss in 1990s


H. Paul Rico, organized crime squad

Dennis Condon, organized crime squad

John J. Connolly Jr., Bulger’s and Flemmi’s handler

John Morris, organized crime squad supervisor

Lawrence Sarhatt, special agent in charge (SAC) early 1980s

James Greenleaf, special agent in charge (SAC) mid-1980s

James Ahearn, special agent in charge (SAC) late 1980s

Robert Fitzpatrick, assistant special agent in charge (ASAC)

James Ring, assistant special agent in charge (ASAC)

Nicholas Gianturco, organized crime squad

Tom Daly, organized crime squad

Mike Buckley, organized crime squad

Edward Quinn, organized crime squad

Jack Cloherty, organized crime squad

John Newton, special agent

Roderick Kennedy, special agent


Robert Long, Massachusetts State Police

Rick Fraelick, Massachusetts State Police

Jack O’Malley, Massachusetts State Police

Colonel John O’Donovan, Massachusetts State Police commander

Thomas Foley, Massachusetts State Police

Joe Saccardo, Massachusetts State Police

Thomas Duffy, Massachusetts State Police

Richard Bergeron, Quincy police detective

Al Reilly, federal Drug Enforcement Administration (DEA)

Stephen Boeri, federal Drug Enforcement Administration (DEA)

Daniel Doherty, federal Drug Enforcement Administration (DEA)

Jeremiah T. O’Sullivan, federal prosecutor, Justice Department

Fred Wyshak, federal prosecutor, Justice Department

Brian Kelly, federal prosecutor, Justice Department

James Herbert, federal prosecutor, Justice Department


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 said. Bulger then offered the boy a quick but crucial lesson in history and bloodlines: both their fore-bears were from Ireland. They were hardly strangers.

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.”


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 streetcar 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.”

Because 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 casework, 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 a court order required the FBI 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 realizing 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 FBI handlers closely monitor informants. 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 then rises to the top of the underworld? What if the FBI protects the informant by tipping him off to investigations other police agencies are conducting?

What if murders pile up, unsolved? If working folks are threatened and extorted, with no recourse? If a large-scale cocaine ring, time and again, eludes investigators? If elaborate government bugging operations, costing taxpayers millions, are leaked and ruined?

This could never happen, right? A deal between the FBI and a top echelon informant going this bad?

But it did.

Today we know that the deal between Bulger and the FBI was deeper, dirtier, and more personal than anyone had imagined, and it was a deal that was sealed one moonlit night in 1975 between two sons of Southie, Bulger and a young FBI agent named John Connolly.


Boston, April 2000

Introduction to the Paperback Edition

In 2000 we published the first edition of Black Mass: The Irish Mob, the FBI, and a Devil’s Deal. Much has happened since the initial publication. Many of the so-called mighty have fallen, ranging from corrupted FBI agents past and present to the upper echelon of the Bulger Gang. In the years since Black Mass a slew of other books have been published about Bulger and the FBI, creating, in effect, a Bulger genre all its own: books by other journalists, gangster tell-all books by former members of the Bulger gang, and, more recently, inside accounts by investigators who pursued Bulger only to confront a corrupted FBI blocking their path. The FBI agent at the center of the scandal, John J. Connolly Jr., was convicted on November 6, 2008 of second-degree murder for plotting with Bulger to kill a man who was set to cooperate with investigators against them. Connolly, now seventy-one, is imprisoned in a Florida jail. Most significantly, the central figure in the historic scandal, James J. “Whitey” Bulger Jr., after being a fugitive from justice since 1995 and on the FBI’s Ten Most Wanted List, was captured on June 22, 2011 in Santa Monica, California, where he’d been hiding in plain sight while living as a retiree with his longtime companion, Catherine Greig. Black Mass is a narrative account of the FBI’s dark deal with Bulger, revealing its origins, Bulger’s reign of terror during the 1980s while protected by the FBI, and, finally, the public disclosure in the 1990s of the deep and toxic FBI corruption. With new developments has come new information, and we are grateful to have the chance to update the story of the FBI and Bulger that is Black Mass.


January 2012


The Prince of Darkness is a gentleman.




Under a harvest moon FBI agent John Connolly eased his beat-up Plymouth into a parking space along Wollaston Beach. Behind him the water stirred, and further off, the Boston skyline sparkled. The ship-building city of Quincy, bordering Boston to the south, was a perfect location for the kind of meeting the agent had in mind. The roadway along the beach, Quincy Shore Drive, ran right into the Southeast Expressway. Heading north, any of the expressway’s next few exits led smack into South Boston, the neighborhood where Connolly and his “contact” had both grown up. Using these roads, the drive to and from Southie took just a few minutes. But convenience alone was not the main reason the location made a lot of sense. Most of all, neither Connolly nor the man he was scheduled to meet wanted to be spotted together in the old neighborhood.

Backing the Plymouth into the space along the beach, Connolly settled in and began his wait. In the years to come Connolly and the man he was expecting would never stray too far from one another. They shared Southie, always living and working within a radius of a mile of each other in an underworld populated by investigators and gangsters.

But that came later. For now Connolly waited eagerly along Wollaston Beach, the thrum of the engine a drag to the buzz inside the car that was like an electric charge. Having won a transfer back to his hometown a year earlier, he was poised to make his mark in the Boston office of the nation’s elite law enforcement agency. He was only thirty-five years old, and this was going to be his chance. His big moment in the FBI had arrived.

The nervy agent was coming of age in an FBI struggling with a rare public relations setback. In Congress, inquiries into FBI abuses had confirmed that the late FBI director J. Edgar Hoover had for years been stockpiling information on the private lives of politicians and public figures in secret files. The FBI’s main target, the Mafia, was also in the news. Swirling around were sensational disclosures involving a bizarre partnership between the CIA and the Mafia also unearthed during congressional investigations. There was talk of a CIA deal with mafiosi to assassinate Cuba’s Fidel Castro as well as murder plots that involved poisoned pens and cigars.

Indeed, it suddenly seemed like the Mafia was everywhere and everyone wanted a piece of the mysterious and somehow glamorous organization, including Hollywood. Francis Ford Coppola’s movie masterpiece, The Godfather, Part II, had played to huge audiences when it opened the year before. A few months earlier the picture had won a slew of Oscars. Connolly’s FBI was now deeply into its own highly publicized assault on La Cosa Nostra (LCN). It was the FBI’s number-one national priority, a war to counter the bad press, and Connolly had a plan, a work-in-progress to advance the cause.


  • "Black Mass should prompt a reevaluation of the uses and misuses of informers by law enforcement officials throughout the country."—New York Times Book Review
  • "[Shows] how fragile FBI integrity can be when the good guys lose sight of [the] truth, the rules, and the law."
    Washington Post Book World
  • "[A] jaw-dropping, true-life tale of how two thugs corrupted the FBI."

    Baltimore Sun
  • "Bone-chilling . . . one of the best nonfiction reads of the year . . . a powerhouse of a book. Dick Lehr and Gerard O'Neill . . . write like veteran novelists, weaving scene after jaw-dropping scene into a tapestry of sickening American corruption."
    New York Post

On Sale
May 22, 2012
Page Count
448 pages

Dick Lehr

About the Author

Dick Lehr, a professor of journalism at Boston University, has won numerous national and regional journalism awards. He is a former investigative reporter, legal affairs, and magazine writer for the Boston Globe, where he was a Pulitzer Prize finalist in investigative reporting. He is the author of The Fence: A Police Cover-up along Boston’s Racial Divide, an Edgar Award finalist for best nonfiction, and coauthor of the New York Times bestseller and Edgar Award winner Black Mass: Whitey Bulger, the FBI, and a Devil’s Deal, and its sequel, Whitey: The Life of America’s Most Notorious Mob Boss. He lives outside Boston with his wife and four children.

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