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When John Connolly Jr. retired from the FBI in 1990, the 49-year-old agent was celebrated by his office for doing more than almost anyone else to close down the New England Mafia. On September 16 this year, Connolly was sentenced to ten years in prison—the maximum sentence allowed—for racketeering, obstruction of justice, and making false statements to investigators. The felony convictions stemmed from his mishandling of what the FBI calls top-echelon informants, especially James "Whitey" Bulger and Stephen "The Rifleman" Flemmi of South Boston's Winter Hill Gang. For nearly two decades, Connolly allowed the pair of stool pigeons to extort and kill while they funneled him leads about the activities of their rivals, the notorious Rhode Island-based Patriarca family, which hawked pornography and ran gambling rackets on everything from dog races to jai alai, blackmailing and murdering along the way.
The misdeeds of Connolly were exposed not by the FBI, where at least two supervisors turned a blind eye to his tactics, but by the unlikely crusade of a federal judge. Judge Mark Wolf began to question bureau tactics after presiding over the 1990 trial of Patriarca family members, which yielded high-profile convictions largely thanks to evidence from Connolly's informants. In the trial's aftermath, Wolf conducted marathon hearings to investigate Connolly's tactics.
As a 30-year-old Department of Justice lawyer in 1976, Wolf had helped draft guidelines to govern the FBI's use of informants, specifying how agents should assess informants' reliability and providing for periodic review by a U.S. attorney to guard against compromising relationships. In 1998, Wolf held an extraordinary ten-month hearing about the FBI's handling of Bulger, Flemmi, and other informants, and followed up with a 661-page decision that served as the blueprint for the investigation that undid Connolly. When Connolly was finally prosecuted this May, Wolf appeared as a witness against him.
In his heyday as a special agent, Connolly was a brash operator who expressed no qualms about his line of work. "I'm sorry, they're never going to be angels," he said about informants. "They're going to be sociopaths." These days, the official line at the bureau is that Connolly was no angel either. "Every organization that's staffed by human beings is subject to the frailties of human nature," proclaimed Charles Prouty, Special Agent in Charge of the FBI's Boston office. But while FBI officials are quick to portray him as a rogue and an anomaly, the material uncovered by Wolf suggests something else.
In Wolf's version, Connolly was handpicked to handle mobsters by a bureau looking to tighten the relationship between agent and informant. In the late 1960s in Boston, Connolly was teaching high school by day and studying law at night. A mutual acquaintance on the Boston police force had brought Connolly to the attention of Dennis Condon, a federal agent who was about to make an informant out of Whitey Bulger. Bulger was a leader of a small-time operation known as the Winter Hill Gang, which ran gambling rackets out of an auto repair shop. Condon understood that Connolly and Bulger shared Irish roots in South Boston. Better yet, Connolly had spent time as a volunteer for Whitey's brother Billy, then a rising star in the Massachusetts House of Representatives and later the president of the state senate. When Connolly joined the FBI, Condon helped him climb within the bureau and eventually to succeed him as the agent in charge of Bulger and Flemmi.
Connolly proved as much of an asset to his informants as they were to him. When New Jersey police uncovered a Winter Hill scheme for fixing horse races in 1978, Connolly swooped in to shield Bulger and Flemmi from federal prosecution. The pair continued to help him infiltrate the Patriarcas; they also went on to kill at least four people in the next five years. The pressure to make a case against the Patriarcas intensified in June 1989 after a gun battle and a related murder. At an International House of Pancakes in the Boston suburb of Saugus, gunmen showered plaster onto tables where families were eating breakfast. The target of the unsuccessful hit was "Cadillac" Frank Salemme, a few days out of prison and on his way to becoming a key player in the Patriarca hierarchy. Salemme, like the man whose body was found in the Connecticut River later that day, represented the Hartford faction of the Patriarca clan—his injuries that morning (he was shot in the chest and leg) marked an escalation of a turf war between the Boston faction and the rest of the Patriarca clan.
The surge in violence gave the FBI's Boston office a new mandate to end the family's reign. Connolly knew where to go: Angelo "Sonny" Mercurio, another family man from Boston, had set up the hit on Salemme and had been an FBI informant since Flemmi brought him around years earlier. Under pressure from the feds, Mercurio helped the FBI place a pea-sized bug in a home in a Boston suburb. The bug picked up a Patriarca induction ceremony rife with Mafia-speak ("Stay the way youse are-don't let it go to your head," advised a boss), including each inductee's pledge, if need be, to kill his own son.
Wolf let the jury hear the tape of the induction ceremony, and it helped convict Raymond "Junior" Patriarca, the don of the family, and four associates on charges of racketeering and conspiracy. Wolf sentenced Junior to eight years, a term the appeals court ordered Wolf to reconsider, this time taking into account the crimes of the underlings Junior oversaw. Wolf added 23 months to his sentence.
Meanwhile, after Connolly's retirement, prosecutors had begun to close in on Bulger, Flemmi, and Salemme, who had assumed Junior's responsibilities running the day-to-day operations for the Patriarcas. What prosecutors didn't know was that Bulger and Flemmi were working for the feds. In early 1995, Connolly got word to them and Salemme that they were about to be indicted for gambling and dealing drugs. Salemme and Flemmi dawdled and were captured; Bulger took the hint and remains a fugitive. The racketeering case against the three went to trial before Judge Wolf in 1997, with prosecutors still oblivious to the defendants' ties to the FBI.
The new case brought the FBI's tapes back to Wolf's courtroom—and this time, they pointed accusingly at the FBI. Anthony Cardinale, Salemme's defense attorney, got suspicious when he heard background whispers of FBI agents critiquing the performance of an informant present on the tape but absent from the warrant request. Further investigation led Cardinale to the discovery that the FBI had applied for countless warrants for bugs and wiretaps without disclosing that many of the characters expected at the taping were government informants. Warrants for hidden recording devices are supposed be a last resort, approved only when the government has exhausted less intrusive methods of gathering evidence. The misrepresentation to the judge who approved the warrants allowed Cardinale to argue that the surveillance tapes should be excluded. Wolf responded to Cardinale's motion with the ten-month evidentiary hearing that probed previously sealed FBI files.
In September 1999, the judge published his mammoth opinion. Under headings like "Dining with 'Donnie Brasco' " and "The Guard Rails at the South Boston Liquor Mart," Wolf laid out the web of relationships that connected the FBI, its informants from the Winter Hill Gang, and the Patriarcas. Wolf wrote, "The FBI made Bulger and Flemmi, who were previously acquainted but not close, a perfect match. In Boston, Flemmi and Bulger uniquely shared an antipathy for the LCN"—La Cosa Nostra—"a desire to profit criminally from its destruction and, most notably, the promised protection of the FBI."
Judge Wolf's own testimony against Connolly centered on an anonymous letter the judge received in March 1997, when he was considering Cardinale's request for a hearing. The letter, written on department stationery and ostensibly from three Boston police officers, charged that a Boston detective was so obsessed with nailing Bulger and Flemmi that he had fabricated evidence against the two. The letter's authenticity came into question after an FBI raid turned up a stash of Boston police letterhead at Connolly's post-retirement office and a witness testified that Connolly had shown him part of the letter. The testimony from Wolf painted the letter as a forgery and added to the mound of evidence that helped convict Connolly of obstruction of justice.
In devoting so much time to unraveling the FBI's files and revealing its informants, Wolf straddled the line between arbiter and advocate. To some, his single-minded, even obsessive focus smacked of wounded pride and indignation. He felt "personally betrayed," recalls Ralph Ranalli, the reporter who covered the case for The Boston Globe and wrote a bestselling book about it. "And I think it was hard for him to let go."
Three appellate judges reversed parts of Wolf's big decision in language that suggested misgivings which went beyond the explicit grounds for reversal. Judge Bruce Selya, a respected 14-year veteran of the United States Court of Appeals for the First Circuit, wrote in the panel's decision that Wolf's ruling had "no principled basis." Wolf had held the government to the specific guarantees against prosecution given Bulger and Flemmi by their handlers at the FBI, who seemed to have the authority to offer immunity. The appellate court found otherwise, stating the view that since only prosecutors have actual authority to grant immunity, assurances made by FBI agents aren't binding.
At issue was a legal principle, but not a moral one. In this ruling and in another six months later, Selya didn't question Wolf's account of deep-rooted FBI misconduct. The second opinion credited Wolf with performing a "significant public service" in calling attention to the FBI's "unholy alliance."
When the appellate court sent the case back to Wolf, the judge responded in just 12 pages. He continued to flog the FBI. This time he made clear that the Boston office wasn't the FBI's only problem, citing examples in which New York agents had tipped informants about upcoming investigations against them. The judge summed up his criticism: "I expect much more misconduct has been masked by the secrecy in which the FBI has operated its confidential informants and the deference it has demanded and almost always received from the Department of Justice."
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