The Underboss

by Dick Lehr

  He would not embarrass himself the way a mawkish Larry Zannino had. Instead, he sat watching the judge, his chin resting on his hand, as the judge polled the jurors. He heard each juror repeat the conclusion. Guilty. Guilty. Twelve times. Angiulo’s shoulders rose slightly. He burped.

  “You were wrong again, Dick,” he told Connolly in the lobby during a brief recess prior to sentencing. The recess lasted only ten minutes. The judge had no discretion in sentencing—an accessory to murder was treated under state law as if he committed the murder himself, meaning he got the mandatory life prison term without parole. The state term would begin after he’d served the forty-five years he received from his federal racketeering conviction. He would die in prison.

  But even though Angiulo held his tongue, there were other signs that the fight was draining from him. When it came time to leave the courtroom, there was a weary resignation about him. In contrast to his snarling resistance to being handcuffed by Quinn four years earlier in the North End restaurant, Angiulo turned from the defense table and searched out one of the two state policemen assigned to guard him. Using pantomime, he asked the guard if he would have to be cuffed: He held up his arms and crossed them at the wrists, with a question on his face. The trooper nodded. Angiulo shrugged and nodded back.

  Two guilty verdicts and a sentence to die behind bars could do that to a wiseguy, even Gennaro J. Angiulo.

  “Well, gentlemen, it appears this book is now closed,” the judge said as he stood and left. “You want to say anything?” asked the reporters who huddled around the sixty-eight-year-old Angiulo. The dethroned mafioso ignored them. He shook hands with his son and then they kissed one another on the cheek. “Take care, now,” he said quietly. He repeated the gestures with his brother. “Don’t give up.”

  Conclusion

  For Gennaro Angiulo, the frigid, fateful night that the FBI broke into his headquarters marked the beginning of the end, a slow, steady slide into ignominy by one of the most entrenched Mafia leaders in America.

  For the FBI, the 1981 bugging of Angiulo’s office was a triumph that has stood the test of time—the convictions of twenty-two top mobsters have all stuck and, in May of 2001, Angiulo’s forty-five year sentence was reaffirmed. Angiulo has been in jail since the night he promised agents that he would return to his dinner table before his pork chops were cold. Even with “good time,” his release date would come in his ninety-first year. The FBI flattened his crime family and drastically altered the landscape of Boston’s underworld.

  But what price glory? Just beneath the surface of spectacular success was a simmering scandal that has rocked the FBI to its core. For, backstage during the Angiulo investigation and the rest of the 1980s, the bureau played a dangerous game of favoritism with Angiulo’s arch rival—legendary Irish mobster James J. “Whitey” Bulger. The FBI protected Bulger in exchange for his over-rated information. Before this sad saga was over, the bureau ran interference for Bulger by subverting investigations by other agencies and alerting him to the identity of other informants-informants who ended up dead.

  FBI agent John Morris stood at the crossroads of both stories. As Globe reporters, we’d first met Morris in 1987 while interviewing the dozen agents who brought down the Angiulo crime family with shoe leather and brainpower. It was a virtuoso performance and Morris rightly relished his role as supervisor of the organized crime squad that had swelled to forty agents for the final assault on 98 Prince Street.

  But John Morris had feet of clay. Just as he deftly pushed the Angiulo case along, he became hopelessly compromised in his dealings with Bulger, tipping him off to investigations by the Massachusetts State Police and the U.S. Drug Enforcement Administration and alerting him to other informants working against his interests. Shortly after Angiulo was ensnared in the early 1980s, Morris began taking cash bribes from Bulger.

  After publishing our anatomy of the Angiulo case in The Boston Globe, we next encountered Morris when we set out to do a biography of the incongruous Bulger brothers, William the younger and Whitey the bad. In 1988, they were at the top of their respective games—Bill was the iron-fisted president of the Massachusetts Senate and James was the dominant gangster in Boston. We decided to build on our Angiulo relationship with Morris by approaching him on the delicate matter of Bulger’s rumored status as a protected FBI snitch. On deep background, Morris confirmed that Bulger was an informant and that, through John Connolly, he had become the tail wagging the dog. But Morris had a hidden agenda of his own: He wanted to force Bulger into retirement to protect himself. Since he began taking cash gifts from Bulger in June 1982, Morris Black Mass, related one of its darkest eras. Among other things, it revealed how Morris and Connolly pulled Bulger’s bacon from the fire by enlisting Bulger in the holy war against Angiulo. In a brilliant tactic, the two agents conscripted their prized informant to make a cameo appearance at 98 Prince Street so the agents could then fold him into a massively-documented T3 affidavit.

  After all the paperwork was already completed and the T3 document was ready for submission, Connolly and Morris concocted walk-on roles for both Bulger and Flemmi. The agents then tagged the gangsters’ names onto the long list of confidential informants already included in the affidavit. The agents could now cite the document as proof to their boss that Bulger was “crucial” in the Mafia takedown. Years later, Morris admitted Bulger was not needed in the case and played a negligible role in establishing probable cause that Angiulo’s office was the center of a criminal enterprise. But for Bulger, his mission had a delicious double purpose—he parlayed his stock with the FBI by sinking his gangland rival.

  Weaving in and out of both plots, some heroes of the Angiulo case became backstage villains or bit players in the deadly Bulger disaster. When a federal judge ruled that Flemmi did not have an enforceable immunity deal and would have to stand trial, he found eighteen agents had violated the law or internal rules in dealing with the longtime informants. In addition to Morris and Connolly, three of them worked the Angiulo case—agents Ed Quinn, Mike Buckley, and Nick Gianturco.

  Indeed, no one escaped the ghosts of 98 Prince Street. Jerry Angiulo’s business address had a trap door for all who crossed the threshold.

  The list of Prince Street victims starts with Jerry Angiulo and his three surviving brothers. Two of his brothers were incarcerated for more than a decade. Jerry’s release date from the federal penal system is May 2010. Jerry was done in by the team work of detested Irish cops and Irish crooks. Angiulo had acquired a lifelong disdain was increasingly terrified that Bulger would get caught and—in a deal with prosecutors—cough him up as a bribe taker.

  After we disclosed Bulger’s ties to the FBI, the story peaked quickly and then fizzled. It glimmered as a faint ember until Bulger and Flemmi were indicted in 1995. Bulger escaped and remains at large but Flemmi was arrested and mounted a defense that proclaimed he and Bulger were promised immunity from prosecution by the FBI in exchange for information about the Mafia. When a federal judge held hearings on Flemmi’s claims, the FBI’s dirty laundry tumbled out into public. The bureau of the 1980s was portrayed as a breathtaking American version of Upstairs Downstairs. The split screen showed how agents purred along the high road after the Angiulos, assembling evidence in the light of day. At the same time, in the dank basement of law enforcement, some of the same agents were protecting the murderous Bulger as he absorbed the dislodged business from the wreckage of the Angiulo empire.

  The dangerous dichotomy was never more evident than during the frantic final months of the effort to get court approval for putting bugs into 98 Prince Street. As detailed in Chapter Five of The Underboss, Morris’s squad, working hand-in-glove with a young prosecutor, weathered several setbacks in producing sufficient “probable cause” to justify the installation of microphones in Angiulo’s office walls. By late in the fall of 1980, the work was done. Between the meticulous surveillance work of the FBI squad and the first-hand observations of at least six confidential informants, th
e prosecutor had cobbled together a compelling and copious affidavit, known as a “T3” application, to present to a federal judge for review. It was ready to go with nary a line in it from the coddled informant Whitey Bulger. But up from the basement came a crisis that threatened the subterranean alliance with the Irish gangster. State Police had lodged a complaint contending that FBI agents had subverted one of the state’s investigations of Bulger.

  The basement brigade took over and just as The Underboss focused on the FBI’s finest hour, our second book on the bureau, for all things Irish while he grew up in the ethnic strife of the North End. The later scandal even diminished the luster of Ed Quinn, the widely respected stand-alone hero of the Angiulo case. During Quinn’s reluctant testimony at the Flemmi hearing, it came out that the star agent had protected Connolly during a debriefing of an underworld figure offering explosive information about Bulger’s domineering relationship with Connolly. The list ends with John Morris, whose career was in tatters, and John Connolly, facing a massive racketeering indictment.

  As detailed in Black Mass, the collusion between Bulger and the FBI confirmed Angiulo’s worst fears. In some ways, he had been set up to make Whitey Bulger look good. It was too much to take lying down. In October 2000, the deposed Mafia chief filed his own motion for a new trial on the claim he was framed by Bulger and Connolly. “It was a dream solution,” Angiulo wrote, “to establish probable cause and necessity for the wiretap to frame and sink Angiulo.” The court rejected his petition in 2001, but in January 2002 Angiulo was at it again. He filed yet another motion in the U.S. Federal District Court in Boston. In it he argued that FBI corruption included defrauding the federal court twenty-two years earlier to win permission to bug his 98 Prince Street office and that his conviction should therefore be thrown out. To this day, he fights on from behind bars.

  It was cold comfort, but Angiulo could take some satisfaction from the indictments against John Connolly, his old nemesis who enjoyed provoking him with slow strolls along the Mafia turf on Prince Street, conspicuously dressed as the dapper G-man and looking to jaw with Angiulo. One of the charges against Connolly was that he cooked the books to hide Whitey Bulger’s decade-long crime spree. At the top of the list of false reports was Connolly’s fiction about Bulger’s “crucial” contribution in getting bugs into Angiulo’s suite. It took two decades, but what goes around, comes around. Connolly’s masterstroke is now part of the case against him.

  Acknowledgments

  For a story that first ran in The Boston Globe and was later expanded into a book, we would like to thank the following people: retired Publisher Bill Taylor for his ongoing support of The Spotlight Team’s efforts; retired Editor Jack Driscoll for supporting the idea of turning the Mafia series into a book and for his helpful suggestions after reading the manuscript; the late Sal Micciche for his advice, legal and otherwise; Christine Chinlund, a Spotlight Team colleague who worked on the Mafia project, for her writing suggestions on the final draft; former Spotlight researcher Mary Elizabeth Knox for her invaluable fact-checking and historical research; Kevin Cullen, a Globe reporter who helped make the original newspaper series a success; the late Bernadette Rossi Lehr for her suggestions after reading the original drafts more times than she bargained for; the Globe library staff for their unstinting cooperation; John and Nancy Lehr for their steady interest in the book; Harry Goldgar for first showing a seventeen year old the pleasures of writing; and, finally, several persons in law enforcement and on the fringes of the underworld who unfortunately cannot be named publicly. They know who they are.

  Index

  Adonis, Joe

  Alexander, Paul

  Alger, Horatio

  American Revolution

  Amico, Joe

  Anastasia, Albert

  Angiulo, Caesar

  Angiulo, Danny

  Angiulo, Donato

  Angiulo, Frank

  Angiulo, Gennaro J. (“Jerry”): arrest of; and Barboza; and the bug inside Prince Street; business acumen of; childhood of; and the Coast Guard; and Cohen; and the Combat Zone; fall of; indictment of; invulnerability of; and LaFreniere; military service by; nicknames for; preoccupation of, with RICO; Quinn as the “Irish tormentor” of; rise of; and “The Wave,” ; and Zannino’s scare tactics

  Angiulo, Giovannina

  Angiulo, James “Jimmy Jones,”

  Angiulo, Jason Brian

  Angiulo, Mike

  Angiulo, Nicolo (“Nick”)

  Apalachin, meeting of the national Mafia at

  Armstrong, Neil

  Attorney General (United States)

  Bailey, F. Lee

  Bank of Boston

  Barboza, Joseph

  Bates, Dick

  Bennett, Walter

  Bennett, William

  Benny, Jack

  Berrigan, Daniel

  Bevilacqua, Joseph A.

  Bonanno, Joseph

  Bono, Chubby

  Boston Globe, The

  Boston Strangler (Albert DeSalvo)

  Brahmin culture

  Bratsos, Arthur C. “Tash,”

  Bridgewater State Prison

  Brown, Steven

  Bruce, Lenny

  Buccola, Filippo (“Phil”)

  Buckley, Michael, Jr.

  Bulger, James J. “Whitey,”

  Caffrey, Andrew A.

  C and F Importing

  Capone, Al

  Capote, Truman

  Carmel Trucking

  Carroll, Daniel

  Carson, Johnny

  Carter, Jimmy

  Caruana, Mickey

  Castellammarese War

  Catholicism

  Chalmas, James

  Cincotti, John

  Cintolo, William

  Civil War

  Clark University

  Cloherty, Jack

  Coakley, Daniel

  Coast Guard

  Coffey, Timothy

  Cohen, Harvey

  Collins, Wendy

  Colombo, Joseph

  Combat Zone

  Communism

  Concord Reformatory

  Condon, Dennis

  Congemi, Salvatore

  Connolly John

  Connolly, Richard J.

  Coolidge, Calvin

  Costello, Prank

  Coyne, James P.

  Cream Puff Bandits

  Cuchiara, Frank

  Cullen, Jim

  Da Nang

  Deegan, Teddy

  Depression

  DePrisco, Thomas J., Jr.

  DeSalvo, Albert (Boston Strangler)

  DeVincent, Richard

  DiNisco, Ernest

  DiSeglio, Rocco

  Dog House

  Donati, Joe

  Donlan, Brendan

  Donlan, Tom

  Drug Enforcement Agency (United States)

  Eastwood, Clint

  Ebb Tide

  Eighteenth Amendment

  FBI (Federal Bureau of Investigation): and the assassination of King; and Barboza; and the Berrigan brothers; and the fall of Angiulo; Operation Bostar; transcripts; videos

  Federal Investments

  First Circuit Court of Appeals

  Fitzgerald, John

  Flemmi, Steve

  Flemmi, Vincent

  Folsom Prison

  Fox, Louis

  Franklin, Benjamin

  Frizzi, Connie

  Gallo, Phil

  Gambale, Richard

  Gambino, Carlo. See also Gambino crime family

  Gambino crime family

  Garrity, W Arthur

  Genovese, Vito. See also Genovese crime family

  Genovese crime family. See also Genovese, Vito

  Giacone, Philip

  Gianturco, Nick

  Gianturco, Thomas

  Gotti, John

  Granito, Sammy

  Gravano, Salvatore

  Great Depression

  Gustin Gang

  Hogan, Rose

 
Hoover, J. Edgar

  Huntington Realty

  IRS (Internal Revenue Service)

  Jay’s Lounge

  Jews

  Jordan, Bobby

  Justice Department

  Kazonis, William “Skinny,”

  Kefauver, Estes

  Kelly, Joe

  Kennedy, Pete

  Kennedy Robert E

  King, Martin Luther, Jr.

  Kottmyer, Diane M.

  La Cosa Nostra

  LaFreniere, Walter

  Lamattina, Ralph

  Larson, Carl

  Lennon, John

  Limone, Peter

  Limone, Salvatore

  Lombard, Barbara

  Lombardo, Joseph

  Lucchese, Thomas

  Luciano, Charles “Lucky,”

  Luciano Commission

  McDonough, Patrick “Sonny,”

  McDowell, Gerry

  Magaddino, Stephano

  Magaliocco, Joseph

  Maranzano, Salvatore

  Marfeo, Willie

  Massachusetts State Police

  Masseria, Joseph

  Mather, Cotton

  Matthews, Kenneth

  Medeiros, Humberto

  Meeting, of the national Mafia

  Morris, John

  Mouse Trap (club)

  Muloney, Herbert

  Nelson, David S.

  New England Organized Crime Strike Forces

  North Shore Association for Retarded Citizens

  O’Brien, Carlton

  Operation Bostar

  Organized Crime Strike Forces

  Orlandella, Johnny

  O’Sullivan, Jeremiah T