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Whitey & the FBI | Part 1: Crossing the line

Agent, mobster forge a pact on old Southie ties

“He knew I’d never help him, but he knew I’d never hurt him.’’ - Former FBI agent John ConnollyFile photo

This five-part series by the Spotlight team was prepared by editor Gerard O’Neill and reporters Dick Lehr, Mitchell Zuckoff, and Shelley Murphy. Today’s installment was written by Lehr and Murphy.

Under a harvest moon, FBI agent John J. Connolly eased his beat-up Plymouth into a space along a deserted Wollaston Beach in Quincy. He sat waiting. Behind him, the ocean stirred and, farther off, the Boston skyline sparkled.

It was the fall of 1975, a time when the city was in the grip of a nightmare -- the busing crisis -- and striving toward a dream -- a World Series.

But the FBI agent had other things on his mind.


The passenger door suddenly opened. Seemingly from nowhere, the visitor Connolly had been expecting slid into the front seat. It was James J. "Whitey’’ Bulger, responding to Connolly’s request for a meeting.

"What the hell did you do, parachute in?’’ Connolly asked the gangster, who had parked his car several blocks away and carefully come up behind Connolly from the beach.

Under the cover of darkness, the two men then started talking about a deal that would leave an indelible mark on law enforcement in Massachusetts.

Bulger, already a legend in the making, would agree to provide the FBI with underworld secrets. His "handler’’ would be Connolly. At 35, he was 11 years younger than Bulger, but a fellow native son of South Boston and already a devoted Bulger family partisan. They’d started out in the same housing project in Southie, where Connolly was tantalized by tales of a flamboyant streetfighter named Jimmy, and awed by the more serious and studious brother of future political fame, Billy.

Lining up Bulger as an informant was surely a coup in the FBI’s crusade against the local Mafia, which ran the most dangerous of racketeering enterprises. Indeed, to this day, Connolly ardently defends the deal, calling it "a brilliant business decision’’ that destroyed a Mafia family.


But the arrangement would veer wildly off track.

The nation’s elite crime-fighting agency gradually was co-opted, finally careering off a cliff in its protection of the prized Bulger. It was a scandal in progress for two decades, but one always kept tightly under wraps, a closely guarded FBI affair.

Last year, however, the bureau was required to confirm publicly what it had always steadfastly denied, even after the Globe published a report in 1988 disclosing the troubling ties between Bulger and the FBI.

But more startling than the belated official admission were the details about a deal that was deeper, dirtier, and more personal than most anyone had imagined.

The alliance between the FBI, Bulger, and his sidekick, Stephen "The Rifleman’’ Flemmi, featured a handful of agents and two gangsters who quickly became intoxicated with themselves and their power. They’d meet for dinner, socialize, and at least on one occasion, Bill Bulger himself popped in, according to recent testimony.

If they’d wanted to, Whitey Bulger and Flemmi could have held their wine glasses up high and toasted their success in outwitting not only the Mafia but the dozens of state troopers, federal drug agents, and local cops who tried relentlessly to build a case against them.

They also exchanged gifts, money, and secrets, but now the party is over. The history of crimefighting by the FBI Boston office no longer centers around a string of celebrated Mafia takedowns in the 1980s; it now requires a cold retelling incorporating the dealings between Bulger and a tarnished law-enforcement agency.


In eight days last April, John Morris, Connolly’s former supervisor, staggered the Boston office with his confessions about payoffs and leaks, about his being seduced by Connolly’s brash patter and ties to the Bulger brothers, about his own corruption in taking bribes from Whitey Bulger that, in some instances, he said were brought to him by Connolly.

Today a fuller account can be assembled from interviews, the sworn testimony of agents, and from once-secret FBI files about the fugitive Bulger, Flemmi, and Mafia boss Francis "Cadillac Frank’’ Salemme, all now charged with racketeering.

Taken together, the materials reveal the deep commingling of two groups the public would ordinarily expect to be at odds: FBI agents and two powerful underworld gang leaders.

Looking back, one thing is certain: The deal struck in 1975 proved to be career-enhancing for the two principals. Connolly rode Bulger to star status in the Boston office as a valued handler of top-echelon informants, and Bulger rode his ties to the FBI to enormous underworld power and riches. During the recent hearings, Connolly refused to testify under oath, citing his Fifth Amendment right against self-incrimination, and prosecutors have refused to immunize him as they investigate possible criminal charges against the former agent.

But Connolly, who retired in 1990, insists he has done no wrong. In Globe interviews, he said that from the start the FBI and the Justice Department allowed Bulger and Flemmi to commit certain crimes short of murder and approved of how he managed the pair. Now, said Connolly, he’s the scapegoat.


"They’re desperate to find someone to hang this all on and they’re certainly not going to blame themselves,’’ Connolly said. "They go down the ladder and find the guy who’s holding the ladder and blame him. That’s what’s happening here.’’

But other agents have taken the witness stand and placed Connolly in the middle of the FBI skullduggery, as the chief manipulator of events that benefited a gangster he’d first met as a boy in South Boston, a chance encounter at a corner drugstore that Connolly says felt "like meeting Ted Williams.’’

Boyhood ties to South Boston

Connolly’s boyhood revolved around the Old Harbor tenements, the first public housing project in New England. Nearby lived the Bulgers, who’d taken up residence there when the project first opened in 1938.

The unruly Jimmy, the oldest Bulger later nicknamed Whitey because of his blond hair, was already the talk of the project as a leader of the Mercer Street gang. Billy Bulger, six years older than Connolly was quieter, more cerebral, and studious. Though the Bulger brothers took off in different directions, they would each rise to the top in their chosen professions -- one in crime, the other politics.

The young Connolly admired Billy Bulger, followed him home on Sundays after Mass at St. Monica’s, and was impressed by his bookishness. Whitey was more the unseen hellion, and not until Connolly was eight years old did he actually meet him.


Wandering into a corner drugstore to eyeball some penny candy, one of Connolly’s pals whispered, "There’s Whitey Bulger.’’ Impulsively, the skinny but tough-looking teenager offered to buy the boys ice cream cones. While his friends eagerly placed their orders, Connolly hesitated, taught never to accept anything from strangers. Bulger, always one to take charge, quickly did so.

"Hey kid, I’m no stranger,’’ Connolly recalls Bulger saying. "Your mother and father are from Ireland. My mother and father are from Ireland. I am no stranger. What kind of ice cream do you want?’’ Connolly chose vanilla and Bulger hoisted him onto the counter to receive his treat.

Their next encounter came later that same year. Connolly found himself in a skirmish over a ball with some older boys. Outnumbered, he was getting the worst of it. Suddenly Bulger was there and scared the assailants away. "He appeared out of nowhere, but I was glad he showed up when he did,’’ recalls Connolly.

Connolly’s family moved out of the project and uptown to City Point when he was 12. He grew up, attended Boston College at Billy Bulger’s urging, and then joined the FBI. By the 1950s, Whitey Bulger was a bona fide gangster, and in 1956 he was apprehended following a wild spree of robbing banks. Pleading guilty, Bulger was sentenced to 20 years in federal prison. He spent a few years in Alcatraz, volunteered to take LSD in government-run experiments to shorten his sentence, and returned to Boston after an early parole in March 1965.

By the time of the fateful meeting at Wollaston Beach 10 years later, Connolly had been in the Boston office of the FBI for two years, having won a transfer from New York in 1973. Bulger, meanwhile, was an established force in the Somerville-based Winter Hill gang that was immersed in loansharking, illegal gambling, and fixing horse races.

Bulger had also teamed up with Flemmi, who was already several years into his own deal with the FBI. The arrangement had proven useful to both sides. The FBI obtained inside criminal information and Flemmi got the FBI off his back. Bulger had even been approached in the early 1970s by Connolly’s FBI supervisor, Dennis Condon, but nothing much had come from that overture.

Then came Connolly’s pitch. He had the inside track Condon did not. Bulger, several years later, would tell an FBI supervisor "he has a close feeling towards John Connolly because they both grew up in the same neighborhood.’’

"I just want you to hear me out,’’ Connolly recalls telling Bulger that first night at the beach. Word on the street was that his Winter Hill gang was on the verge of a war with the local Mafia run by Gennaro "Jerry’’ Angiulo in a dispute over the placement of mob-controlled vending machines.

Connolly says he warned Bulger that it wouldn’t be a battle fought on the street because the powerful Angiulo family would use its corrupt police contacts to set-up Bulger and his gang.

"I hear Jerry is feeding information to law enforcement to get you pinched,’’ Connolly said. "I have a proposal. Why don’t you use us to do what they’re doing to you? Fight fire with fire.’’

The offer was that simple: Use the FBI to eliminate his Mafia rivals. If that alone wasn’t reason enough, there was a bonus: Cooperating meant the FBI would not be out looking to take Bulger down, and percolating at that very moment was a loansharking probe in which his name had surfaced.

Bulger was intrigued, and he told Connolly : "You can’t survive without friends in law enforcement.’’

The agent and the gangster met again several weeks later to cement the deal. Connolly recalls Bulger saying that while the Mafia can "play checkers, we’ll play chess.’’

So it began: Whitey Bulger and the FBI.

Bulger as an ‘investment’

In the beginning the arrangement may have actually made sense.

"Without informants, we’re nothing,’’ former FBI Director Clarence Kelly once said. Moreover, beginning in the 1970s, the FBI was in hot pursuit of its announced national priority -- La Cosa Nostra. In this regard, Bulger and Flemmi were well positioned, two ruthless enforcers whose gang regularly did business with the local Mafia based in Boston’s North End.

In fact, Flemmi was a favorite of several key Mafia leaders who would try unsuccessfully over the years to persuade him to join up with them.

To this day, Connolly is unwavering in his belief that the FBI’s deal with Bulger and Flemmi was a no-brainer. In his view, they gave the FBI the mob. "We got 42 stone criminals by giving up two stone criminals,’’ he says. "What’s your return on investment there? Show me a businessman who wouldn’t do that.’’

And he says the historic deal was his alone to make: "Whitey only talked to me because he knew who I was and he knew me from when I was a kid. . . He knew I wasn’t going to be wired up on him. He knew I was friends with his brother Bill.’’

But Bulger and Flemmi were not sad-sack bookies merely satisfied with rounding up illegal bets while tipping off the FBI to some underworld dirt.

Ambitious and violent, the two men were soon in charge of the Winter Hill gang, committed to expanding their own criminal network. Bulger became, as Connolly himself noted in an early FBI report, the "leader of the Irish Mafia.’’

In recent interviews, Connolly elaborated further, saying the pair "were just as dangerous, if not more dangerous, than the Mafia.’’ Though they never confessed to murder to him -- and he says they were never given license to kill -- Connolly now acknowledges they are killers. "I don’t think they ever killed anyone who wasn’t trying to kill them or wasn’t going to rat them out,’’ he says. "They would only kill people who were a threat to them.’’

But throughout the 1980s, Connolly spent much of his time deflecting trouble, as the tips from other informants and police agencies piled up naming Bulger and Flemmi as suspects in murders, shakedowns, and big-time drug profiteering.

Even after some fellow FBI agents began thinking the deal stunk -- believing that the FBI should be targeting Bulger, not pampering him -- the resilient Connolly repeatedly outmaneuvered his foes. He went to work creating a pile of paperwork that soft-pedaled Bulger’s role in criminal activity and turned the bureau’s dependency on the gangster into an addiction.

Unsealed for the first time during the past year, Connolly’s memorandums and reports reveal an agent asserting two main storylines that in combination served to protect his prized informant. He regularly embellished the value of Bulger’s information while minimizing complaints about his crimes.

It was as if once Connolly put down in writing something Bulger supposedly said, then it must be true; if Bulger protested his innocence to murder or some other crime for which he was a suspect, then that was it, end of story.

Early in 1981, for example, during the FBI’s successful bugging operation of Mafia headquarters, agents taped Mafia underboss Gennaro Angiulo bragging about Bulger and Flemmi: "I’ll tell you right now, if I called these guys right now they’d kill any (expletive) body we tell ‘em to.’’

Less than two months later, Connolly staked out a contradictory view, applying what amounted to public-relations polish to Bulger’s reputation: "It should be noted that the current Title III (bugging) operations have established that source (Bulger) is not a ‘hit man’ for Jerry Angiulo, as has been contended,’’ wrote Connolly in a memo.

Nearly from the start in the late 1970s, two views of Bulger were in irreconcilable competition: the minimalist view constructed and cared for by Connolly, and the view being assembled by the dozens of state troopers, Boston and Quincy policemen, and federal drug agents whose own informants and surveillance efforts were revealing Bulger as an extortionist, loanshark, and drug trafficker. The latter believed the true challenge was to nail both the Mafia and Bulger -- not just the Mafia, as the FBI would have it.

In the end, the outside view has prevailed: rackeeteering charges against the fugitive Bulger portray him as a violent underworld kingpin and drug profiteer. But Connolly’s view was the one that carried the day inside the FBI for nearly two decades; as Bulger’s handler, his reports served as the primary basis for decision-making by the agency’s chain of command. Over time, the FBI adopted a policy of denial.

Agents socialize with criminals

To be sure, Connolly was not alone. Right away he enlarged the circle of agents with ties to Bulger and Flemmi, relations that grew social and more personal.

In 1979, Connolly called his pal Nick Gianturco, said he had a couple of guys who wanted to meet the FBI agent, and then dropped by with Bulger and Flemmi. Over time, they would go on to dine, drink, and exchange presents. Despite explicit FBI rules prohibiting taking gifts, the now-retired Gianturco recently testified under oath he was unaware of the longstanding ban.

Gianturco has said of Connolly: "He was by far the best informant developer I’ve ever seen in the bureau.’’ Over time, the band of Boston agents enthralled with Connolly’s way with Bulger included Jack Cloherty, Tom Daly, Mike Buckley, and two top supervisors, Dennis O’Callaghan and James Ahearn.

More dinners followed, and at one gathering two retired agents who’d been friends of Connolly’s in New York joined in on the fun. "It was obvious. . . Whitey Bulger and Steve (Flemmi) were friends of Connolly’s,’’ one of the agents, Jules Bonavolonta, told FBI investigators last year.

Today, Connolly makes no apologies about the intimate get-togethers. He exchanged gifts with the gangsters, mostly at Christmas time -- small things, like a book and, one time, handcarved hunting knives. "You can’t be around those guys for 15 years and not like them,’’ he said.

"There was a respect and an admiration there, no question about it, but always looming in the background was the realism of what he did for a living and what I did for a living,’ Connolly added, referring to Bulger.

Eventually, Connolly’s style would come in for criticism. "I had a meeting with John Connolly in my office,’’ testified James A. Ring, one of Connolly’s former supervisors, during recent court hearings. "And I told him that what I was observing was contacts with Mr. Flemmi and Mr. Bulger with, I thought, mistakes that a first-year agent wouldn’t make.

"That’s when I pointed out to him that I didn’t need consultants and that informants were not friends and that informants were informants, that we should learn from them, and they should not learn from us.’’ But this was too little, too late: Ring admitted he never documented his concerns nor mentioned them to the agent in charge of the Boston office.

Then there was John Morris, the former head of the FBI’s organized-crime squad in Boston. In a series of admissions, Morris testified this past spring how he had hosted secret dinners for Bulger and Flemmi, taken $7,000 in payoffs, and warned them to stay away from a bugging operation.

Morris admitted that as Connolly’s boss he had signed off on a mythic view of Bulger that Connolly was manufacturing. Moreover, not only had Morris approved the paper trail Connolly was amassing, but he, too, had facilitated the bureau’s minimizing of Bulger’s criminality.

It was Morris who in 1981 issued the virtual open-ended promise of FBI protection for Bulger, a memo that falsely proclaimed the Winter Hill gang was decimated and therefore did not require any further pursuit by the bureau.

But the FBI cocoon created for Bulger and Flemmi went beyond assembling a pile of dubious paperwork. Right from the start, the FBI deflected trouble from inside and outside the bureau.

In the late 1970s, for example, a frightened restaurant owner in Dedham told Norfolk County authorities that Bulger and Flemmi had threatened to kill him if he did not pay off a loan. The promise of a case against the two gangsters was self-evident. But after the FBI stepped in, the matter went nowhere.

Meanwhile, Connolly and Morris were scrambling to extinguish a threat to Bulger and Flemmi posed by one of the FBI’s own investigations -- a race-fixing case against the Winter Hill gang that was nearing indictment in early 1979. In court recently, Morris testified that Bulger and Flemmi insisted at the time that they were not involved in the race-fixing. Taking them at their word, Morris said he and Connolly then sought out federal prosecutor Jeremiah T. O’Sullivan and succeeded in persuading O’Sullivan to drop the pair from the case. In a Globe interview, Connolly said that O’Sullivan set only one condition: that the pair agree not to kill the government’s star witness, Anthony "Big Tony’’ Ciulla. O’Sullivan’s lawyer, Hugh Scott, declined comment.

Flemmi himself has added to recent revelations about the race-fixing case. Last year in a sworn statement, he first corroborated Morris’s account by saying, "The FBI had seen to it that we would not be named in the indictment.’’ But he went further, revealing that the FBI had leaked the timing of the indictment so he and Bulger could warn a couple of associates to get out of town. The leak was one of at least a dozen provided by the FBI, said Flemmi, who added that it became the bureau’s "practice’’ to tip them off.

From at least 1979, the hooks were in -- a habit of protecting Bulger at all costs -- and it would only worsen once the payoffs began and the corruption mounted. Through it all, Bulger, in reports authored by Connolly and others, comes off as the model of calm, a man on top of the underworld dance.

Even when an angered State Police hierarchy in 1980 began suspecting something rotten was festering between Bulger and the FBI, the gangster seemed unfazed. In late 1980, Connolly and Morris met at least twice with Bulger and Flemmi to discuss concerns about their safety if word got out that they were informants.

The snitches told them not to worry; they sure weren’t.

"Both Bulger and Flemmi emphatically stated that no one in the underworld would believe that they were informants,’’ the agents reported afterwards. "It would be too incredible.’’

Boston’s prince of the city

The cocksure Connolly has always been a man about town, moving easily among different circles of power -- crime, politics, and the media. Over the years, he was relieved of much of the grunt work, the donut-dependent stakeouts and grinding street-surveillance work. Instead, he was a prince of the FBI’s Boston office, able to come and go as he pleased and displaying a knack for cozying up to power.

“He had the same flip cockiness wise guys have. . . Made no bones about his close ties to Billy Bulger,’’ said a retired federal prosecutor in an interview, adding that agents like Connolly end up protected by the FBI’s institutional elitism. "You couldn’t do anything about it,’’ he said. "They were all insulated in their arrogance. You just could not permeate it from any other place in law enforcement. They knew best.’’

Connolly was nothing if not connected: He charmed journalists with FBI stories. And when a new top agent was assigned to oversee the local office, which consists of about 200 agents, Connolly made a practice of taking the incoming boss to meet his lifelong friend and mentor, Bill Bulger, the former state Senate president, now president of the University of Massachusetts.

Connolly retired in 1990 to a high-salaried security position with Boston Edison, where he works today. He’s an FBI raconteur, spinning yarns about stalking the Mafia, as well as the idea that Whitey Bulger actually helped maintain order on the streets of Boston as a kind of arm of the police.

And along the way he’s made some dubious proclamations. After the truth about the FBI’s ties had emerged, Connolly sought out a top editor of the Globe to deny the link -- and to insist he’d never even talked to Bulger.

The truth is there were hundreds of meetings and conversations between the two men, a fact now part of a larger truth tumbling out of locked FBI closets faster than chroniclers of crime and politics can keep up with. Even after his retirement, Connolly continued to talk with Bulger and Flemmi; at one point he reached out to the gang leaders after hearing a rumor the Mafia was looking to kill him. Connolly, who last year told government investigators about this encounter, said Bulger and Flemmi assured him "that the threat was nonsense and that if they had heard of the threat they would have contacted both him and the FBI to prevent such activity.’’

To the end, Connolly says his handling of Bulger was above reproach. Former agents like Morris, he says, are liars. More importantly, the deal was vital to achieve the FBI’s string of heady successes against the Mafia in New England, the gemstone being the 1981 bugging of Mafia headquarters at 98 Prince St. in Boston’s North End.

This is Connolly’s refrain: Bulger and Flemmi provided the key probable cause the FBI needed to win court approval to bug the Mafiosi. "They were without a doubt the two single most important sources we ever had,’’ he says.

But Connolly’s take on history appears skewed. Evidence has emerged contradicting the very claim on which Connolly and the FBI have staked the reputation of their Boston office -- that Bulger may have been bad, but he gave us the Mafia. Put bluntly, the FBI’s addiction to Bulger was not a prerequisite to taking down Gennaro Angiulo, the underboss of the Mafia in New England.