Law enforcement officials' lament about an elusive foe: Where was Whitey?

By Christine Chinlund, Dick Lehr and Kevin Cullen
Globe Staff / September 20, 1988

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Five years ago, on a cloudy April morning, federal agents barreled into a cinderblock warehouse in South Boston the minute the huge garage doors blinked open like two heavy eyelids.

Daylight revealed the booty hauled from the piers a mile away: 10 tons of marijuana. Valued at $6 million, bale upon bale was jammed into trucks gassed up and ready to go.

Not a bad haul, along with the six men nabbed inside.

But agents savoring the bust were brought up short when they learned a potential bonus prize had apparently gotten away. By 10 minutes, informants later disclosed, the agents had missed James (Whitey) Bulger. The agents went back to look for fingerprints, but no such luck.

So where was Whitey?

The question has become the lament of law enforcement. The man designated a killer and crime boss by the 1986 President's Commission on Organized Crime has risen steadily in the past decade to the top of the underworld with nary a scratch.

Since 1980, local police, state troopers and federal drug agents have hunkered down behind windows, squeezed into entryways, and wormed around car interiors -- all in an effort to tail Bulger or conceal a tiny microphone in Bulger's car, his home or in the public telephones he frequently uses.

They have assembled the evidence to win court permission to monitor Bulger, but then have been repeatedly outmaneuvered before they could make the pinch. The bug goes in and suddenly Bulger stops talking.

The near-misses of Whitey Bulger have been law enforcement's most conspicuous failure in a decade of unprecedented accomplishment that saw the downfall of Howie Winter, overlord of the Winter Hill Gang, and, bigger still, of Gennaro Angiulo, the longtime Mafia underboss of Boston.

It is an elusiveness that Bulger, who served his only stretch of hard time three decades ago, has sustained throughout his life. "People all knew him, but nobody knows him," observed one longtime acquaintance. At 59, he is one of Boston's all-time mystery men and the aura of mystery fosters contradictory tales -- about his ruthlessness but also about his soft spot for the South Boston that has always been his base. The result is a paradoxical portrait of a reputed killer: the legend of Whitey as a not-so-bad bad guy.

The image has served him well. He has confounded everyone. The Mafia has a love-hate thing with him. "They're with us," Ilario M.A. Zannino, the tough Mafia lieutenant, once said about Bulger and his associates, only to bluster another time about how he would like to blow them all away with machine guns.

And the Federal Bureau of Investigation has for years had a special relationship with Bulger that has divided law enforcement bitterly and poisoned relations among many investigators, the Spotlight Team has learned.

"Isn't he a great guy?" said an FBI agent about Bulger, according to another agent who feels the FBI should bust Bulger, not be beguiled by him.

For Whitey, the one willing to walk the high wire, the confusion provides the breathing room to prosper and survive.

"We're all good guys here," he proclaimed in 1984 as he waited politely for outwitted federal drug agents to finish retrieving a microphone he had discovered in his car. "You're the good-good guys, and we're the bad-good guys."

Ever since his wild days of robbing banks, there have been few public glimpses of Bulger. But there have been plenty of secret ones -- from the Quincy police, state troopers and federal drug agents who have spent large portions of their professional lives chasing Bulger.

In the past decade, those sources said, Bulger has carved out a lucrative niche with his associate Stephen (The Rifleman) Flemmi: They control South Boston, Roxbury, Jamaica Plain, a piece of the South End and parts of Quincy and Lowell. With the Mafia in disarray, some now consider Bulger the most powerful mobster in Boston. "If they choose to be, Whitey and Flemmi are today as powerful as any Mafia regime," said one investigator.

Using a low-key style, the two are believed to function, in effect, as landlords -- collecting rent from anyone doing business on their turf, whether it is running numbers or drugs. In recent years, South Boston's piers and warehouses have been used as a staging area for drug distribution, a set-up that police saycould only happen with Bulger's blessing.

"At the very least, he's getting protection money from drug runners," said one agent. "Legally, that puts him in their service." But to others, collecting tithes is the extent of his role in drug trafficking. Bulger, said another, is in the "business of money, not drugs." And the money game includes shaking down drug dealers as well as lending funds at sky-high rates to loan sharks and gamblers who need cash quickly.

It is a business conducted mostly after hours. Like most major mobsters, Whitey is a creature of the night. His routine is to avoid a routine, having become ever more wary of being followed.

For a time in 1980, he and Flemmi operated out of a garage on Lancaster Street, near North Station. They waited outside for their appointments, each standing with his arms folded across his chest, not a hair out of place, not a shirt button out of line, as they stared down passersby.

There was the 50-year-old Whitey, still flexing the results of a lifetime of lifting weights, first in his bedroom in the Old Harbor tenements and more recently in health clubs.

On the street outside the garage, his demeanor was usually dour. He has a benign, Irish face, but somehow it is always clear he is not approachable. There is something firm and flat about the eyes, which look like marbles when he is angry.

Making visits to talk to the inseparable pair were a Who's Who of Boston's mobsters: Larry Zannino, Danny Angiulo, Nick Giso, Frank LePere, Connie Frizzi. They came carrying briefcases, and money was seen changing hands in an office inside.

Sidekick Nicky Femia usually stood watch, a beefy, gun-toting hit man who was murdered in 1983. Femia's lack of discipline and fitness was the sort of thing that set off Whitey Bulger the health fanatic, who only occasionally sips wine, does not smoke and does not permit anyone near him to smoke. Coming out of the garage office one day, Bulger spotted the 240-pound Femia using the polished hood of a black Chevy as a tabletop for a feast of McDonald's hamburgers and greasy French fries. Bulger grabbed the fast food and began throwing it into the face of the back-pedalling henchman twice his size.

It was like a scene from a mob movie, and the sudden burst of anger stunned the state troopers who were watching secretly from across the street. The troopers were left with an indelible impression similar to one a South Boston man had when he first saw Bulger's violent side 40 years ago. "I saw him get into a fight, and he just beat the piss out of the guy. Oh, he was vicious. And he wasn't that big. The other guy was bigger. But he was tough, and everyone whispered, 'That's Whitey Bulger.' "

But the garage near Boston Garden was only a pit stop for a man whose business makes perpetual motion a lifestyle. For a while, he shifted his meetings to the back room of a smokeshop near City Hall. Or he would make the rounds himself, ducking into the Cafe Pompeii in the North End to see Donato Angiulo, who ran his family's loan-sharking out of the Hanover Street coffee shop.

Mostly, however, Bulger has always commuted between pay phones. Many days, Bulger and Flemmi could be seen fishing in their pockets for dimes. They would make a call at the corner of Old Colony and Dorchester streets in South Boston, then go down to the phone at West Broadway and Dorchester Avenue. Then into a variety store on Broadway, followed by a quick swing into a bar. For a while, the favorite spot was the bank of pay phones outside the Howard Johnson's off the Southeast Expressway.

From there, they would head off to meet someone inside a row house on a narrow South Boston side street or in the parking lots of the factories at Fort Port Channel. They cruised around in leased cars that were changed frequently to guard against surveillance. For weekends, Whitey has kept a Cadillac or Jaguar -- the kind of luxury car he has always prized, going back to the projects when he not only had the wheels few others could afford but a car that sported the big fins and shiny chrome of the era.

The phones, the rotating cars and the open air meetings were all calculated moves. Said a source, "He's compulsive. The agents would do his trash . . . and there was a lot of ash, he would burn stuff in his fireplace. He would rip things into tiny little shreds, almost like he had a shredder in his apartment."

They were days in the early 1980s that often ended at a private club in Roxbury controlled by Flemmi. And they were days that periodically featured Bulger's legendary temper -- a mean streak that first surfaced in his teen-age fighting days and became part of underworld folklore by the 1970s, when a wiseguy once warned a secretly wired loan-shark victim that he would rather tangle "with a cobra" than cross Whitey Bulger.

At 3:05 p.m. on Sept. 25, 1980, according to a state police report, a trooper who was following Bulger and Flemmi witnessed Whitey's distaste for riffraff in his hometown: Bulger suddenly jumped from his car and grabbed a wino, who had been slumped on a Silver Street stoop. With Flemmi standing by, Bulger beat the man about the face, kicked him, then, in a final flourish, took the wino's hat and threw it down the street. Bulger got back in the car laughing and drove away. When the plainclothes trooper approached the wino, the man pushed him away. "I don't know nothin'," the wino said. "And leave me alone."

Few have a clue about the size of Bulger's South Boston cadre, but no one doubts his strength. "I can't tell you that anybody I've worked with has any idea what kind of muscle he has -- just that everybody's scared to death of him," said a former federal prosecutor.

But what Bulger may lack in numbers, compared to the beefier Mafia, he more than makes up for in guile and style. He has also always been different things to different people. To his mother, who died in 1980, the daring kid with the reddish-blond hair and easy smile was always Sonny. To his friends and siblings, he has always been Jimmy and a fierce loyalist.

Whitey has spent a lifetime helping out the mothers living in South Boston's Old Harbor Village tenements, where the Bulger family was among the first residents in 1938. "If he was coming up the street, and I had the

carriage going down just four stairs, he'd yell, 'Wait a minute, Mrs. Dame,' " said Sally Dame, recalling five decades ago.

To the troopers who often followed Bulger into South Boston, there was always a noticeable change in his manner. Whitey Bulger, who crossed his arms and stared through those who came to pay him tribute at the downtown garage, would say hello to children and show deference to elderly women. Said a detective about Bulger today, "He would stop and open a car door for a lady, stop traffic." He has distributed baskets and turkeys in the housing projects at Christmas, donated money to the youth sports teams and sent money to the families of men in jail.

But, for the most part, the homefront talk of Whitey is restricted to his cordial relations with adults as a boy. In interviews, many neighbors said no one ever openly discusses Sonny-Jimmy-Whitey's professional life, which dates back to a 13-year-old's first unruly journeys up to Mercer Street and petty crime. It is a rock no one turns over.

Said a friend: "He's a hell of a guy; it's just if you are on the wrong side. . ."

The turkeys and the donations, pulled off with a politician's touch, have helped create the good-bad guy that is Whitey Bulger. Except for Flemmi, he has never stuck with anyone long enough that they could know otherwise. Even in the beginning, Whitey was there but not there; in his early teens he hung around with a few of the Shamrocks but was never himself a member of that gang. Then came his association with the Killeen brothers of South Boston and, after that, with Howie Winter. It has been a lifetime of mergers and acquisitions.

He has been a schizophrenic puzzle to the most powerful underworld enterprise, the Mafia. During three months of secret bugging of the Angiulos in 1981, the Mafia relished the idea they could call on Bulger and Flemmi, if need be, even to kill. "I'll tell you right now, if I called these guys right now they'd kill anybody we tell 'em to," underboss Gennaro Angiulo claimed one winter afternoon. Later that year, Angiulo's lieutenant Zannino discussed the fate of a wiseguy who had erred by not paying Bulger and Flemmi long overdue money. Noted a soldier to Zannino, "I know if Stevie or Whitey sees him. . ."

"They're going to hit him," Zannino said.

But this same cast of Mafiosi could suddenly turn on Bulger and Flemmi when the subject became the pair's $245,000 debt. "When did they ever come down here and give me a quarter?" Gennaro Angiulo complained one day about the obligation that always soured his mood. "And I'll tell you something, I don't think they intend to pay it, if you want my honest opinion."

The harangues against Bulger and what was left of the Winter Hill gang increased, as his elusive, independent ways occasionally proved too much for the Mafia. Angiulo began spreading the word he was tiring of the Irish hoods over at the Lancaster Street garage. The brutal Zannino related this to his men after a night of drinking at his big-stakes card game in the North End, a night that was tape-recorded by the FBI. "They got a bad attitude," Zannino reported.

"Why don't we go in that garage, right now? With machine guns," clamored one of the soldiers.

"We'll go tomorrow morning at 9 o'clock," Zannino said, stoking a flame that never flared beyond the North End backroom.

"We'll go bust right in the joint."

Gushing Mafia machismo, Zannino concluded, "You think they're with us? We'll kill every one of these Irishmen."

For the past decade, Bulger has kept the Mafia at bay, managing what one source called a "loose association" rooted in being both ally and a potential enemy. They were the sort of ties that Howie Winter first used to keep the Italians off balance -- elaborate gamemanship that called for friendly conversations, but with everyone taking a seat with their back to the wall.

They were ties that Flemmi had on his own, as he carved out a niche in Roxbury back in the early 1960s. Together, the Bulger-Flemmi team carefully

nurtured their special standing, which has served them well. The pair dealt directly with Angiulo, who usually preferred go-betweens to insulate himself

from non-Mafiosi. Said a source, "The Mafia treats them with kid gloves."

And it is a respect that Bulger trades on, his reputation rivaling that of the Mafia's own legendary enforcer. "Whitey is the most like Zannino on the scene today . . . ," said one investigator. "But he is 100 times smarter. He's selectively brutal. That's the difference."

The Mafia is not the only force that Bulger has succeeded in keeping at arm's length. Even more impressive is the distance he has maintained from the law. Since Bulger left prison in 1965, he has only been in court twice, both for traffic violations. Few Boston police officers have any idea what Bulger looks like and Police Commissioner Francis M. Roache has declined to discuss him.

It is not as if some other cops have not tried.

For most of 1980, the State Police pursued Bulger. Detectives wired the garage, installed bugs in pay phones and tried hiding a microphone in the car Bulger drove. Each time their efforts fizzled. They had a slew of technical difficulties but also security problems: Bulger somehow caught on to their

sleuthing and either began talking gibberish or said nothing at all.

In 1984, federal drug agents took a swing. The Drug Enforcement Administration put a bug in a window of Bulger's condominium in Quincy and, when that failed, installed a microphone in his car door. It was the car bug that led to the lengthy, good-bad guy Bulger monologue, as dejected federal agents retrieved the $50,000 in equipment Bulger had found.

The setbacks have left law enforcement officials confused, suspicious and at one another's throat. Bulger, said one source, loves to pit one law enforcement agency against another, "which isn't difficult in this state." If so, Bulger has been triumphant. Few others have ever had such a divisive effect on law enforcement -- a disharmony, The Spotlight Team has learned, rooted largely in the fallout from Bulger's longstanding ties to John Connolly, a member of the FBI's organized crime squad.

Mention Connolly's name today to many who track mobsters and the reply is Whitey Bulger. Mention Bulger's name, the reply is often Connolly, the street- smart agent who also grew up in South Boston and first made contact with the Irish gangster shortly after the FBI transferred him home from New York City in 1973.

Back then, said federal sources, it made sense to have someone in the Boston office keeping open lines with the emerging leader. For Bulger's part, he was hardly the first underworld figure to have a tenuous liaison with the other side. Mobsters frequently shadowbox with agents in a complex game that is sometimes reducible to a single question: Who is using whom?

But as Bulger rose to the top of his game, the Bulger-Connolly tie has been questioned by others in law enforcement, including some inside the FBI. "You can never have (contact with) the top guy," one former official said in criticizing Connolly's continuous link with Bulger. "Because you have the top guy, he's making policy, and then he owns you."

The failures of the State Police and the DEA have created two antithetical schools of thought: that the investigators simply bungled it through

inexperience; or that Whitey has been able to exploit his cachet with the FBI to plan his evasive tactics.

State Police officials felt so strongly that someone within the FBI had tipped the mobsters about the bug that, in an unprecedented case of fingerpointing, they asked the FBI to conduct an internal inquiry. The FBI cleared two agents, and the FBI leadership remains outraged at the suggestion that any of its own would engage in that kind of treachery.

James F. Ahearn, special agent in charge of the FBI in Boston, was unequivocal when asked last month if Bulger has had relations with the FBI that have left him free of its scrutiny.

"That is absolutely untrue," said Ahearn. "We have not had evidence that would warrant it and if we do develop anything of an evidentiary nature, we will pursue it. We specifically deny that there has been special treatment of this individual." He declined to make any further comment on the matter and instructed Connolly not to speak on the subject.

Fallout from the bugging fiasco at the Lancaster Street garage did not end at fingerpointing. More bitterness followed in the summer of 1981 when the State Police discovered a small item on early retirement, tagged onto the state budget package, that would have forced those who ran the department's intelligence division to retire immediately. The item was later removed, but police officials never figured out which legislator or staff person inserted the item into the budget, or why. Many in law enforcement felt the mysterious action was a warning shot at the State Police commanders who, the year before, had authorized the Lancaster Street investigation targeting Whitey Bulger.

In the bitter aftermath, many who were planning the DEA's 1984 probe of Bulger were convinced they should not even tell the FBI, circumventing the policy that the FBI be notified of targeted figures. Despite the nearly universal feeling that no agent had or would intentionally warn Bulger about electronic surveillance, the fear of a leak persisted.

But to avoid a feud, William F. Weld, then the US attorney in Massachusetts, and Robert M. Stutman, then the DEA special agent in charge,

went to see James Greenleaf, then FBI special agent in charge of the Boston office. The FBI, according to federal sources, was offered a role in the Bulger investigation if it wanted one. Several days later, Greenleaf declined.

Interviewed recently about the meeting on Bulger, Greenleaf was evasive. ''Because of the sensitivity of the thing, I can't really comment," he said. Later, he added, "I wish I could comment, there are things that need to be said." But by the end of the brief interview he was backing off entirely

from the subject of Bulger. "I don't recall being in a meeting where that (Bulger investigation) was the topic of conversation."

At the time, the FBI's position confirmed others' worst fears about Bulger. ''It really made you think, why won't the FBI do this guy?" said one high- ranking DEA official.

Even inside the FBI there was a growing feeling by 1984 that the Connolly- Bulger liaison had gone on too long, that it was not producing results, and that it should be abandoned given the critical perception gaining momentum among others in law enforcement. At least one FBI agent refused to work with Connolly. And, while the DEA continued drawing up its plans, there was a move within the FBI, which ultimately failed, to force Connolly to close out the contact with the underworld leader.

"You can't have another government agency running an investigation against a guy that we know," said a federal source familiar with the effort. "It's stupid. It's dumb."

The net result is that when it comes to Whitey Bulger, the FBI has been put on the defensive. Many dubious investigators point back to the race-fixing convictions of Winter Hill mobsters, which began in 1979 and ran through 1982, as the first sign of exemption for Bulger and Flemmi. Of the co-conspirators government witness Anthony (Fat Tony) Ciulla accused of getting a cut of the profits, only Bulger and Flemmi were not indicted.

But Jeremiah T. O'Sullivan, the chief of the US Justice Department's New England Organized Crime Strike Force, who prosecuted the case, said the two were not indicted because "we had no evidence against them outside of Ciulla's word. Very rarely do you indict on just the word of an informant."

"To the people who are whining and complaining, I'd suggest, make a case on them. It ain't nuclear physics. It can be done," said O'Sullivan in a challenge to the law enforcement agencies which have gone after Bulger. "What you've had is some people taking one shot, then walking away crying that there's been a leak. You've got to keep trying."

The explanation does not quiet the critics, who contend the race-fixing case was the best shot anyone has had against Bulger, a shot worth taking with the word of a government witness who proved his credibility in court. They also note that back in 1968 just the word of a government witness put away Raymond L.S. Patriarca, head of the New England Mafia, for five years.

Moreover, O'Sullivan's exhortations to try harder do not explain the existence of at least 14 volumes of FBI files on Bulger -- material that one federal source noted is further proof of the FBI's longstanding relationship with Bulger. "Who else would have that many volumes?" the source asked rhetorically. "Maybe Jerry Angiulo? Patriarca? But they were put away." The extensiveness of the files indicate the FBI has been following Bulger closely for years, but it has never charged him with anything.

Knowledge of the copious FBI files resulted from a Freedom of Information Act request made by the Globe last April. The Globe has yet to receive any of the requested material from the FBI, a delay that one official in Washington explained was in part due to the time it will take to sift through the voluminous material to determine what portions are disclosable.

For the critics, including those within the FBI who have heard Connolly mention Whitey's good-guy deeds in the home district, it is a dangerous situation not unlike the US government hanging on too long with helpful if unscrupulous dictators.

"It's always a tough call about when you go past that turning point where you were using the guy and then he starts using you," said a veteran investigator.

From the dispute, Bulger profits -- his opposition divided, his reputation enhanced. "Other police just throw up their hands and it becomes a free ride," another said. Added a prosecutor about Bulger's apparent omniscience, ''Whitey's got hooks everywhere." If Bulger lacks outright control, it is clear he is on the mind of those running the control tower.

One clue to Bulger's strategic success comes from the nine years he spent in federal prison. He studied extensively, from politics to World War II. But his approach to war was unique. "He would read one guy's book, say Marshall's book, and then he'd go get the book from some German, and he would study the same battle from everybody's perspective," said a friend.

Bulger, it seems, has a knack for the quick countermove. Faced with the prospect of renewed surveillance, he has become more cautious, said sources who monitor his activities.

Less frequent are his visits to the home of his brother, Senate President William M. Bulger, and he has long stopped going to gatherings there on St. Patrick's Day. In the summers, Bulger used to enjoy the afternoon sun in front of the South Boston Liquor Mart, the building which until recently was owned in his name. He has not been sunning himself there this year.

Bulger now goes on the road a lot, sources said, travel being his favorite form of recreation, often with his longtime companion, Theresa Stanley. Indeed, Bulger's last public encounter was an unexpected one a year ago at Logan Airport.

As always, it had a Whitey twist.

Minutes before Bulger and Stanley were going to board a flight to Montreal last September, airport security examining luggage realized Bulger's carry-on bag contained a brick-sized wad of cash. The guard thumbed through the $100 bills, totaling an estimated $100,000. Bulger angrily ignored questions about the money and, when the guard said she was notifying State Police, he took off.

Followed by a guard, Bulger headed quickly for the door. Just as a quarterback hands off a football, he gave the package to another man, who hurried out the door and climbed into a black Chevy Blazer. The guard tried to follow, but Bulger put his foot in the revolving door so it would not budge.

The guard was stuck. The Chevy drove away.

No one knew they were dealing with Whitey Bulger, not State Trooper William Johnson, who responded and found a man dressed in an expensive black jogging suit exchanging harsh words with a security guard. The trooper looked at Bulger's identification -- James J. Bulger -- but still did not make the connection.

Because there was no reason to detain him, Bulger was eventually let go. But not before the trooper spent a couple of minutes trying to figure out what happened. Getting double talk from Bulger, the trooper finally yelled at him to shut up. Bulger, who does not consider himself an ordinary wiseguy, was genuinely affronted. In his best good-bad guy mold, he asked:

"Is that how you treat citizens?"