The Underboss Read online

  Table of Contents

  Praise

  ALSO BY GERARD O’NEILL & DICK LEHR

  Title Page

  Dedication

  Introduction

  Chapter 1 - Cold Pork Chops

  Chapter 2 - The Mob in Boston

  Chapter 3 - The Rise of Gennaro Angiulo

  Chapter 4 - Catch Up

  Chapter 5 - The Wave

  Chapter 6 - Failure

  Chapter 7 - Break-In

  Chapter 8 - Inside 98 Prince Street

  Chapter 9 - An Attempted Murder

  Chapter 10 - The Noose Tightens

  Chapter 11 - Mafia Murder

  Chapter 12 - The Fall Of Gennaro Angiulo

  Conclusion

  Acknowledgements

  Index

  Copyright Page

  Praise For The Underboss

  “The most spectacular single campaign of the 1980s against the Mafia was waged in Boston, where the FBI put virtually the entire Angiulo family behind bars. The Underboss not only chronicles the fall of Gennaro “Jerry” Angiulo ... it provides fascinating detail—and right from the horses’ mouths—of the inner workings of organized crime.... An engrossing story of the good guys winning big, told with insight and chilling effect.”

  —Chicago Tribune

  “Nobody could follow these hair-raising maneuvers better, or write about them more authoritatively.... A riveting book.... Magisterially decodes a ‘battle of wits and stamina’ of almost unbelievable complexity.... A scrupulously researched history of the Mafia in Boston.... The whole story comes to us in the crackling, suspenseful, yet elegant style that is American reporting in its Sunday best.”

  —The Atlanta Journal-Constitution

  “An eminently readable capsule history of organized crime in Boston and ... an absorbing, true tale of cops and criminals.”

  —The Worcester Telegram

  “Fans of George Higgins’ novels will feel right at home here.... This is how the Mob operates.... The full, grimy story.”

  —David Nyhan, The Boston Globe

  “An ‘evil genius,’ Angiulo’s fatal error was to believe the popular wisdom that he was too crafty and too well insulated in his impregnable North Boston enclave to ever be apprehended. This fast-paced, engrossing, and ultimately satisfying story shows how the FBI bridged the mythic moat surrounding Angiulo.... Gripping.”

  —Library Journal

  ALSO BY GERARD O’NEILL & DICK LEHR

  Black Mass: The Irish Mob, the FBI, and a Devil’s Deal

  For

  Janet and Brian and Shane

  Nick and Christian

  Introduction

  The Underboss: The Rise and Fall of a Mafia Family, was first published in hard cover in 1989 and we are pleased that our publisher, PublicAffairs, is now re-issuing the book in an updated paperback edition.

  The Underboss is about a group of FBI agents who accomplished what no one else in law enforcement had come close to doing—they brought down Gennaro J. “Jerry” Angiulo and his four brothers, who had ruled the Mafia in Boston for decades.

  These agents pulled off what no one else in law enforcement had ever attempted—they installed a bug inside the Mafia’s inner sanctum, the Angiulos’ main office at 98 Prince Street in the city’s North End neighborhood. For years, Jerry Angiulo had eyes and ears throughout the tight confines of the largely Italian-American section of Boston, and most in law enforcement viewed the home court advantage as insurmountable.

  But not this band of FBI agents. They succeeded where others dared not even go, and the dramatic tale of the agents in the FBI’s Organized Crime Unit assembling the case against the Angiulos is the heart of the book. To this day, the bugging of 98 Prince Street remains a high-five moment in the FBI’s high-profile national crusade against the Mafia throughout the 1980s. In Boston, the crusade brought down the Angiulos and in New York City the effort eventually netted John Gotti.

  The Boston case stands as one of the first in this string of heady FBI takedowns. It was one of the first times the FBI succeeded in penetrating a Mafia family’s office to secretly record Mafia bosses setting underworld policy and plotting crimes, including murder. The bosses were then convicted in federal court by their own words.

  In addition, the Angiulo case was one of the first instances of federal prosecutors exploiting fully the then largely untested Racketeering Influenced and Corrupt Organizations Act, or RICO, in pursuing the Angiulos in court and winning long prison sentences. Today the term RICO is practically a household reference to describe the legal assault against organized crime. Not back then.

  Finally the early 1981 bugging of 98 Prince Street represents one of the first times the entire top tier of a city’s Mafia family was prosecuted successfully, and the Boston investigation became a model for FBI efforts in other cities later in the decade. In sum, the FBI’s case against Jerry Angiulo was then—and still is—a shining example of the FBI at its dogged, technical best.

  But—and this is a big “but”—much has changed since The Underboss was first published in 1989. We now know that two key FBI agents in the bureau’s crusade against the Mafia were corrupted throughout this era in their informant relationship with two other Boston gangsters—the Irish crime boss James J. “Whitey” Bulger and his sidekick, Stephen “The Rifleman” Flemmi.

  The agents are John Morris and John J. Connolly, Jr. Morris, the supervisor of the Organized Crime Squad in Boston, guided the Angiulo bugging operation reconstructed in The Underboss. Under him, agent Connolly was an informant handler, and he handled Bulger and Flemmi. Over the years, other agents were embroiled in the dirty deal between the FBI and Whitey Bulger, but these two agents—Morris and Connolly, squad supervisor and star informant handler—were in the middle of all of the mayhem.

  The full story of FBI corruption is told in our recent book, Black Mass: The Irish Mob, the FBI, and a Devil’s Deal, a deeply disturbing saga of wrongdoing now regarded as the biggest informant scandal in FBI history. At the same time that the FBI was taking down Angiulo, it was enabling Bulger to take over most of the city’s rackets and to acquire near untouchable status as a killer and kingpin.

  The unraveling of FBI glory began with the disclosure in a 1988 Globe story that Bulger had a special relationship with John Connolly. Over time, that single thread pulled loose from the FBI’s veil of secrecy unraveled into a massive FBI scandal that still plagues the bureau today, a scandal that included looking the other way as Bulger murdered at least eleven people while functioning as an FBI informant. More recently, the FBI’s informant practices have become the subject of Congressional hearings.

  Today the Bulger scandal has consumed many of the same agents who performed so well during the Angiulo case. Morris was disgraced for taking bribes from Bulger and has admitted that he obstructed justice by leaking confidential information to Bulger. Connolly was indicted in the fall of 2000 on racketeering charges and for cooking the FBI’s books to hide Bulger’s crimes and for tipping him off to investigations and the identities of other informants.

  Working as investigative reporters for The Boston Globe in the late 1980s, we were deeply involved in both the Angiulo and Bulger stories. In rapid succession, we took a jarring journey through the good, the bad, and the ugly of law enforcement. We did not expect the reporting to take us from writing about one of the FBI’s finest hours in The Underboss to writing about the polar opposite in Black Mass. In this regard, the books are companion pieces: The Underboss still standing as a story of a remarkable bugging operation and Black Mass as a larger history of a band of FBI agents in Boston who lost their way and, in effect, became gangsters themselves.

  In both, we now know that supervisory agent John Morris was a conflicted man in the middle. One an
ecdote captures Morris’s desperate dilemma. Right after the bugs came out of 98 Prince Street, Morris called for a meeting with Bulger and Flemmi so he could play for them a tape fresh from the Angiulo files. Never mind that tape-playing was way off-the-books; Morris was looking to show off and curry favor with Connolly’s prized informants. Renting a room in a downtown hotel, Morris arrived with the recording. Bulger, aware of Morris’s sense of himself as a wine connoisseur, arrived with two bottles of wine to celebrate the downfall of the Mafia. Morris drank while Bulger and Flemmi listened to Angiulo discussing the possible murder of a neighborhood woman who had offended the Mafia underboss. Morris asked: Is this a real threat? No, replied Bulger and Flemmi. Just another sample of Angiulo’s braggadocio. Morris finished off the wine. Too tipsy to drive, Morris had lost control in more ways than one. In a sad caravan, Bulger chauffeured the agent home in a government Ford while Flemmi followed in the gangsters’ midnight black Chevy.

  The ride home capped the shift in power from the good guys to the bad. The lead agent in the Angiulo case had become an intoxicated passenger in a journey that would take him to a personal prison no less confining than Jerry Angiulo’s jail cell.

  1

  Cold Pork Chops

  At 9:00 P.M., about halfway through her meal at Francesca’s restaurant in Boston’s North End, a short, perky brunette told her husband she was going to check in with their babysitter to make sure the kids were okay. Dressed casually in jeans and sweater, she bounced her way among the tightly packed formica-top tables to the pay phone.

  “This is Mrs. Jones,” she said. “Are the children all right?” Because no one was standing near the phone, there was no need for elaborate code talk. She quietly added: “One, four, and five are here. Two and three are not.” As someone approached, she said her good-byes with a flourish of good cheer. “We’ll be home shortly,” she chirped to the babysitter. She hung up and wove back to her seat, smiling sweetly.

  The reassured mother was, in fact, an FBI agent. Her cryptic message told the case agent, Edward Quinn, that Mafia Underboss Gennaro J. Angiulo (number one) and two of his four brothers were at the small Italian restaurant just a few blocks from the bureau’s downtown Boston office.

  On the other end, Quinn made a brisk announcement to an assembled battalion of agents: Jerry, Frank, and Mike Angiulo had ordered supper and were to be arrested before they could finish. He knew that the oldest brother, Nicolo, was ill and at home in Revere. Nick could be grabbed the next day. But it was number three—Donate Angiulo—who worried him the most. Danny was unaccounted for and could wind up in Italy or parts unknown if the FBI didn’t get him that night. Quinn ordered a team of six agents to find the dangerous Mafia lieutenant.

  The agents headed out to smother the North End, looking for Danny’s 1978 black Cadillac, especially around his hangouts, the Café Pompeii on Hanover Street and the Knights of Columbus hall on North Margin Street. Even after nightfall on this September 19, 1983, the unseasonable mugginess from several straight days of ninety-degree heat lingered. The twilight breezes that swept off the inner harbor were less refreshing than sticky.

  Almost as an omen, the month had been a harsh one in Boston. Major developments on the three fronts of interest in a parochial city—politics, sports, and religion—all brought bad news. The local media was dominated by the police commissioner’s struggle with alcoholism; another late-season collapse by the Red Sox; and the unexpected death of the city’s spiritual leader, Archbishop Humberto Cardinal Medeiros.

  But those events occurred on the city’s beat, the public side that any resident or visitor could monitor easily in the newspapers or television. Less detectable was the pulse of Boston’s underworld, that subterranean life where day is night—a time to rest—and night is day—a time to work: hustling numbers; staging craps, barboot games, and Las Vegas nights; taking sports bets; collecting loanshark payments; and, on occasion, ruling that somebody’s life must come to a brutal finish.

  In the North End, Mafia ruler Gennaro Angiulo had sought out a cool spot from the kind of stifling heat that left shirts dark with city grime and arms wet with perspiration. For a late supper, he and two of his brothers had gone to Francesca’s Restaurant on North Washington Street to take up their regular table in a back room.

  His night had begun routinely enough. He and his brothers discussed their various illegal enterprises and then made the short walk from the Mafia boardroom at 98 Prince Street to the favored restaurant. It was a route that took them along streets and past buildings that hadn’t changed in more than a century—despite Boston’s new skyline of skyscrapers that rose in the shimmer of summer heat just a few blocks from their neighborhood. It was a route that took them past tenement buildings where their mother and father first lived as teenagers when they arrived from Italy eight decades earlier.

  The small eatery was situated on one of the boundaries of their thickly settled North End neighborhood, with its narrow alleys and dark streets that were labyrinthian even for a city not known for making much street sense. But this was where the 64-year-old Jerry Angiulo and his brothers felt safe. Here they were born and, for nearly three decades, this was where they controlled a ruthless criminal enterprise considered among the most profitable in the country.

  The North End was already an Italian stronghold when the Angiulos’ parents arrived in the neighborhood in the early 1900s, where they ran a market on Prince Street. And that was the street where the Angiulo boys grew up and where Jerry, with a knack for numbers, realized how millions could be made from efficiently run rackets. Jerry became a commuter in the late 1950s from his mansion in the North Shore community of Nahant, but he always kept his headquarters in the spit of land that jutted out between Boston Harbor and the Charles River Basin. He didn’t budge from Prince Street even though the old neighborhood, by 1983, found itself pressured by the economic revival that was changing the face of most of the city’s downtown.

  But the North End stubbornly resisted the change. There remained the generational and interlocking relationships among neighbors. Most important to the Angiulos, there were still many pairs of eyes and ears looking out and listening in, providing a seemingly airtight network that insulated the mobsters from outsiders.

  It was a home court advantage that agents of the Federal Bureau of Investigation had long considered as insurmountable as that enjoyed by the Celtics basketball team in nearby Boston Garden. The North End was the Angiulos’ defense against an alien and fast-changing city, and when it came to Mafia business, the brothers stuck closely together in their old confines. Frank “Cat” Angiulo, one of Jerry’s younger brothers, who served as an accountant for the myriad bookmaking operations, lived on Prince Street directly across from the office. In fact, Frankie was such a homebody that he never even ventured the few blocks to the famous Quincy Market, the sprawling commercial marketplace that had emerged from the ruins of a warehouse district in the late 1970s.

  In many respects, Gennaro Angiulo, the Mafia chieftain who was seated apart from the other diners at Francesca’s, had led a charmed life. He’d made millions and, for those keeping a scorecard, he was way out front in that endless game of evasion with the authorities that every mobster must take seriously. Since the early 1960s, the nimble-minded Mafia boss had been targeted by every level of law enforcement—city, state, and federal. He’d outwitted them all—serving only two thirty-day prison terms despite a resume that included trials for murder and laundering money stolen in an armed robbery as well as countless grand jury probes. Both prison terms came after the notoriously hot-tempered Angiulo lost his cool during challenges on his turf. The first was in 1966 for assault after he objected to the presence of an Internal Revenue Service agent outside his North End office and slapped the man as two bodyguards stood watch. The other was in 1973 when he assaulted a coastguardsman who dared to board his yacht to inspect it for minor boating violations.

  Those skirmishes aside, the compact, silver-haired Mafia autocrat
was legendary for his ability to skirt the government’s maneuverings, thwarting every move it made. For years, when trouble came, he used his analytical mind to stay one step ahead of prosecutors, interrogating underlings who appeared before grand juries or were questioned by police. What did they ask you? Who asked the question? What did you say? Angiulo combed his underlings’ memories for any small clue to help him fashion countermoves that might include trying to bribe a juror, paying off witnesses for their false testimony, or even killing them if they could not be counted on. But even now, as he sat to discuss business with Frankie and Mike over dinner, Jerry Angiulo sensed the latest FBI offensive was unlike any he had faced before. There had been strong indications this round would be different.

  “I smell a RICO,” Angiulo had been telling his brothers for a couple of years now. He was referring to the Racketeering Influenced and Corrupt Organizations law, the organized crime-fighting tool that had been around since 1970 but had only recently been dusted off and used by the Organized Crime Strike Forces around the country. Angiulo’s senses had been heightened in the first six months of 1981, after a federal grand jury was convened, and many of his bookmaking offices had suffered a series of raids that had rankled and confounded him.

  Enraged at apparent breakdowns in security, he began worrying constantly about the law that made it a crime to operate a criminal outfit. In angry lectures that bordered on tirades, he hounded his brothers about the RICO threat. “They will take your fuckin’ head off,” he pronounced once about the power federal agents had, now that they were armed with RICO. “Nobody’s ever been able to beat it yet,” he complained in another endless monologue to Frankie in which he mixed his personal analysis with readings from the statute. Despite his persistent efforts to find an escape clause in the legalese, Angiulo, in calmer moments of clarity, concluded, “The law was only written for people like us.”