by Dick Lehr
There were other women too, but these were the regulars. While the troopers were never sure where the Chevy might land for the night—Brookline, Randolph, Milton, parts unknown—like clockwork Stevie would pick up Bulger at the housing project around midday. Flemmi would slide over, and Bulger would slip in behind the steering wheel. They realized that Bulger’s demeanor seemed to soften in South Boston, away from Lancaster Street. He greeted kids, waved to mothers, and stopped his car to allow elderly women to cross the street.
But even in Southie he had his moments. One day that summer O’Malley was following Bulger and Flemmi when Bulger turned down Silver Street. Bulger supposedly owned some property on the street, and his girlfriend, Theresa Stanley, lived there. Turning onto Silver, Bulger came upon a group of old men seated on the front stoop of one of the houses. The men were drinking. Bulger hit the car’s brakes and jumped out. The men scrambled off, but one was too slow to react. Bulger hit him across the face, back and forth. The man fell to the ground and curled up. Bulger kicked him. Then he grabbed the man’s hat and threw it down the street. Flemmi, meanwhile, looked up and down the street, keeping watch, but Bulger was done. He and Flemmi laughed hard, got back into the car, and sped away. O’Malley raced over to the bleeding man, but the man was no fool: he waved the trooper off, told him to get away. “I don’t know nothin’ and don’t bother me.” Even a drunk knew better.
While they were assembling their own intelligence about Bulger, the troopers also checked in with their criminal informants. One informant, code-named “It-1,” reported that starting that year “there was a large Money Bank at the garage on Lancaster Street, where the ‘Big Boys’ go to deliver money collected as a result of illegal gaming operations run by the North End. This garage is where the accounts are settled up.” Another informant, named “It-3,” told the troopers that “Bulger is a former lieutenant in the Howie Winter organization and is believed to be assuming control of the operation in Winter’s absence.” Another informant, “It-4,” told them that “Whitey Bulger and Stevie Flemmi were presently overseeing the majority of the sports betting, numbers action, and loan-sharking for the Boston area and in particular the Somerville area.”
The troopers tapped other informants as well, all of whom hooked Bulger and Flemmi up with the Mafia in a flourishing joint venture. By the time July rolled around, Fraelick, Long, and O’Malley felt they had enough probable cause in hand. In open view from the window was a case with the potential to stand as the hallmark of any investigator’s career—nailing the entire lineup, the Mafia and the Bulger gang. The troopers had put up with the squalor of the flophouse, logged the long hours of surveillance, and even gotten a little wacky: on the walls of their room they’d mounted the largest of the cockroaches they killed during the surveillance, transforming the “room kill” into a trophy.
By early July the troopers had witnessed plenty of street action; now they wanted to know what the mobsters were actually saying. They sensed they’d stockpiled enough intelligence and were eager to take their case to the next level—installing a microphone inside the garage.
SEVERAL times that spring, Long, along with his commander, met with Jeremiah T. O’Sullivan, still the top federal prosecutor at the New England Organized Crime Strike Force. Long briefed O’Sullivan on what he and his troopers were witnessing at the Lancaster Street garage. They came up with a plan in which the feds would provide funding for the state police bugging operation. They brought in a local prosecutor, Tim Burke, an assistant district attorney in Suffolk County, to prepare the court papers to win a judge’s approval.
Despite the federal funding, it would be a stand-alone state police effort. No other agency. It wasn’t as if the troopers could not work with the FBI. After all, Long had served as state police commander in Operation Lobster, the joint FBI and state police investigation that had involved Nick Gianturco. But there were the new rumors, especially after the race-fixing indictments when Bulger had eluded prosecution. The rest of law enforcement had begun wondering about Bulger and the FBI. But O’Sullivan, despite what he knew, told Long nothing. It was their case.
On July 23, 1980, Superior Court Judge Robert A. Barton approved Burke’s application for a warrant to bug the Lancaster Street garage. Pumped up, Long, Fraelick, and O’Malley went to work. None of them had had much experience when it came to electronic surveillance, but they’d make up in energy what they clearly lacked in expertise. They’d actually made a trip to Radio Shack to buy the microphones they were going to use. Then, to case the garage’s interior and get a sense of the layout of the office, O’Malley posed as a tourist needing to relieve himself. He wandered into the garage one day, looking lost and looking all around. Bulger confronted him, saying there was no bathroom, and sharply ordered O’Malley out.
It was all trial and error.
The troopers came to call their first attempt “the Trojan Horse.” They obtained a fancy-looking, souped-up van, pulled up the floorboards, and created crawl space for O’Malley. Then they replaced the floorboards, covered them with a shag rug, and filled the van with furniture. With a state police secretary at his side, Fraelick drove up to the garage late one midsummer afternoon. He told George Kaufman that he and his bride were new to Boston and having some car trouble. He was worried about leaving the van with all their belongings overnight on the streets of Boston. What if he pulled the van inside the garage and then first thing in the morning a mechanic could take a look at it?
Kaufman gave his okay and waved the van in. The “newlyweds” thanked Kaufman, promised to return in the morning, and walked off. Kaufman eventually closed up and left too. The plan was for O’Malley to emerge from the van during the night and let a crew in to install the microphones. But none of the troopers had counted on one of the winos from the flophouse across the street setting up right by the garage. O’Malley, bathed in sweat and grime, had no idea what was going on. He was not in radio contact with the others, but he could hear the wino making noise outside. The troopers improvised. Long had one of his crew go out and buy a case of beer. The trooper plopped down next to the wino and began feeding him beers. Once the man passed out, the troopers could move in. But waiting ate up precious time, and just when the man was going down Kaufman unexpectedly reappeared. Kaufman started yelling at the two men drinking at his garage, and he chased them off. By this time it was too late to pull off a bug installation. Eventually O’Malley emerged from his suffocating hiding spot only to learn that Long had called off the effort.
Their next try met with more success.
Early one evening the troopers parked a U-Haul truck snugly next to the garage. The truck not only carried a crew but also created a wall so that no one from the flophouse could look down onto the garage. Most nights the winos and wackos were yelling and hanging out the open windows in the sweltering heat. The truck took care of the flophouse follies. Then, after Kaufman left, two troopers dropped down by the side of the truck and kicked out a bottom panel of the garage door. The troopers crawled in and, with the help of a technician they had hired for the job, installed three microphones—one in a couch, one inside a radio, and one in the ceiling of the office. They left, replacing the panel on the garage door.
Bob Long and his troopers were ecstatic. But the operation went quickly downhill from there. Testing the reception, they faced technical problems. Instead of mobster talk, they were picking up pager calls for doctors at nearby Massachusetts General Hospital. The microphone installed inside the radio didn’t function at all. The one in the couch worked but wasn’t of much use, producing little more than a rush of sound, like a hurricane, when one of the mobsters, especially the oversized ones like Nicky Femia, collapsed into it. But they were getting transmission from the microphone in the office, and that was the prime location; after straightening out the hospital interference, it was soon up and running.
Then the sky fell in.
Bulger, Flemmi, and Kaufman mysteriously started looking up at the windows in
the flophouse. Abruptly they altered their routine. Instead of talking in the office or in the open bays, Bulger and Flemmi held meetings inside the black Chevy. The office was now off limits. The troopers were stunned. They kept monitoring their bugs, but shortly after the gangsters moved their talk to the backseat of the Chevy they had to stop coming to the Lancaster Street garage altogether. Early in August the court order permitting them to bug the garage expired. The troopers had their notes, a pile of great photographs, but nothing more. Bulger was gone.
IN THE days before Long, Fraelick, and O’Malley failed in their bugging attempt, trouble had been brewing for the FBI. It began with a chance encounter at a Friday night party. John Morris, cocktail in hand, sidled up to a hulking Boston detective. The diminutive Morris still managed to talk down to him—the federal agent lording over a local cop. “You have something going at Lancaster Street?” Morris asked with a conspiratorial smile that urged: C’mon, you can tell me.
Taken aback, the detective put on a poker face to mask his surprise. A direct question about another agency’s secret investigation wasn’t expected cocktail chatter at a midsummer party. The question hung in the air, unanswered.
Morris pushed on. “If you have microphones in there,” he said, “they know about it.”
After some more dead air, the police detective finally replied, “I don’t know what you’re talking about.”
The detective moved away from Morris. But his heart was racing. The next morning he called Bob Long. The early morning phone call did not take Long completely by surprise. He had been sensing something was wrong. All that the bug inside the Lancaster Street garage’s corner office was picking up was a jaunty Whitey Bulger commending state troopers for the great job they did patroling the Massachusetts Turnpike. Ball-busting or coincidence?
Long wasn’t entirely sure. But the more he thought it over, a pattern became clear. He and his troopers had watched for months from the flophouse across the street as Bulger harassed anxious gamblers who owed money and bantered with visiting Mafia dignitaries. Then, exactly one day after a bug was up and running inside the garage, Bulger had been praising highway patrols and, more important, changing his routine. Business conversations had moved from inside the office to the backseat of Bulger’s black Chevy parked inside the bay area.
Initially Long had figured that Bulger and Flemmi spotted the troopers across the way. But now word of Morris’s overture made Long realize that the problem was much worse than a blown surveillance. To Long, the gangsters’ new routine wasn’t just one of those things that happened. It was treachery. The call from the police detective confirmed the shocking truth that Long saw through a red haze of fury. And he became transfixed by two questions:
How did John Morris know about the state police bug?
And how did he know Bulger and Flemmi knew?
By Monday morning, August 4, 1980, it was war. The ranking state police officer, Lieutenant Colonel John O’Donovan, was on the phone complaining about the leak to the head of the FBI’s Boston office. The state police and FBI office were already accustomed to tangling over glory and credit for fighting crime in Massachusetts, but this kind of accusation marked the nadir of a strained relationship.
Faced with the angry finger-pointing, law enforcement did what it always does—it held a meeting. The summit at a Ramada Inn in Boston convened four days after Morris’s party blunder. Attending was a who’s who of law and order: O’Donovan and Long from the state police, county prosecutors, Boston police officials, an FBI official, and Jeremiah T. O’Sullivan.
O’Donovan presented the grievances of the state police. Looking around the room, he spiced his indignation with a small bluffing game. He claimed their bug had been “extremely productive” until it was tipped. And he said they knew Bulger and Flemmi were informants. Of course, the state police had no solid proof that Bulger and Flemmi were FBI snitches. But O’Donovan had a strong hunch about Bulger’s possible ties to the FBI, going back to an encounter he’d had with the gangster a couple of years earlier. O’Donovan recalled going to see Bulger at Marshall Motors. The issue was a threat against a state trooper from one of Bulger’s associates in the Winter Hill gang. Packing two guns, O’Donovan stopped by the garage to convince Bulger that any move against a trooper was a stupid idea. Bulger quickly assured the lieutenant colonel that nothing would come of the hotheaded rhetoric. Then the two chatted sociably about life along the law enforcement landscape, with one thing leading to another, and finally to the FBI. O’Donovan mentioned that he preferred the older agents in the Boston office to the younger ones, saying that newer agents like John Morris were too inexperienced in the ways of Boston. He made it clear that he was not impressed by Morris and other young turks.
About two weeks later O’Donovan took a call from a fuming John Morris, who wanted to know why he was badmouthing the FBI with Whitey Bulger. O’Donovan was brought up short and concluded that either the FBI had a bug planted inside Marshall Motors or Bulger was an FBI informant.
Morris’s indiscreet call only compounded O’Donovan’s mistrust for the FBI supervisor. O’Donovan saw the agent as a schemer who maneuvered behind a friendly demeanor. Another time he’d passed along a state police tip to Morris about a fugitive on the Ten Most Wanted List. The same day Morris and several agents raced to capture the terrorist bomber. There was no joint arrest, just an FBI press conference. O’Donovan and his troopers were forgotten on the sidelines.
But none of this was proof of skullduggery. It was just troubling background that an experienced policeman never forgot. And at the Ramada, O’Donovan didn’t get into this kind of history. But neither did he and Sergeant Long disclose that the troopers, despite the setback at the Lancaster Street garage, were planning to take another run at Bulger and Flemmi later in August. Instead, O’Donovan focused on recapping the debacle at the garage, climaxed by his conviction that the FBI had compromised the bug. Between the lines the topic on the roundtable was nothing short of accusing FBI agents of a crime: obstruction of justice.
But the FBI men did not flinch. It was their kind of game. The bureau’s representative, an agent named Weldon L. Kennedy, one of the assistant supervisors in Boston, listened politely to O’Donovan of the state police. Once O’Donovan was done, Kennedy had little to say.
We’ll get back to you, he finally offered. But that was it.
After the meetings, however, the FBI in Boston went into spin cycle. Initially the bureau insisted that Morris had learned about the bug by putting two and two together: first, his own informants from the North End Mafia had detected “new faces” in the area, and second, Morris had heard that Boston police were ordered to stay away from Lancaster Street. To a professional like Morris, there was only one conclusion to draw: something investigatory was under way. Morris even offered that his approach to the Boston cop was a well-meaning bid to use his insight as a warning to the troopers.
But O’Donovan and his troopers viewed Morris’s account as disingenuous at best and, during the weeks after the Ramada Inn summit, made it clear they were not buying the FBI’s explanation. In turn, the FBI moved the tense, interagency dispute up a notch. The FBI said it had learned from its informants that any leak had come from within the state police; the collapse of the bugging operation was the state police’s own fault. The agent who had brought this new juicy intelligence to the table was John Connolly.
BACK at state police headquarters the troopers kept debating what went wrong, going over every move they’d made. They weren’t going to give up, not yet. They’d seen too much of Bulger and Flemmi.
They let a few weeks go by to give Bulger and Flemmi some room to move. Then they hit the street again, riding around to see if they could pick up the gangsters’ scent. It wasn’t easy, especially after the debacle at the garage. Bulger was crafty, a difficult mark. Behind the wheel of the Chevy he employed a number of evasive driving techniques. If he was approaching a traffic light and the light was turning yellow, he acce
lerated and raced through the intersection. Sometimes he simply ran the red light. He drove down a street and suddenly pulled a U-turn and came back at you. Sometimes he drove the wrong way down a one-way street, and Southie seemed cursed with one-way streets. He knew South Boston cold, and he often zigzagged his way through the old neighborhood rather than take a direct route to his destination.
But soon enough the troopers picked him up. Just before Labor Day, Long, Fraelick, and O’Malley established that Bulger and Flemmi had a new pattern, and it revolved around a bank of public pay phones outside a Howard Johnson’s restaurant right off of the Southeast Expressway.
The new routine went like this. Nicky Femia drove into the HoJo’s parking lot, circled around, and then parked. He’d saunter over to the pay phones, look around, stuff a few coins into the phone, and make a call. The black Chevy pulled in a few minutes later, carrying Bulger and Flemmi. Then they climbed out and looked around, and each went into a telephone booth to make some calls. They chatted away, their heads bobbing and turning, always looking out over the parking lot and studying any vehicle that might drive by. Once off the phone, they drove off. The troopers, if they could keep up, followed them to Southie or into the North End, where they met up with any one of the number of underworld figures they used to meet in the bay and office of the Lancaster Street garage.
So far the investigation had focused on loan-sharking and gambling, but the troopers now began to make out the hint of a drug connection. The troopers didn’t know at first who Frank Lepere was; in fact, a number of photographed wiseguys were written up in their logs as “unknown white male.” But showing one such photograph around, the troopers learned it was Lepere, a former Winter Hill associate who’d gone into the business of marijuana trafficking with Kevin Dailey of South Boston. Lepere had shown up at Lancaster Street carrying a briefcase; looking back, Long and his troopers realized “it wasn’t full of candy bars, that’s for sure.” After Labor Day the troopers had followed Bulger and Flemmi from the pay phones to South Boston, where the two gangsters met up with Kevin Dailey. This time Flemmi was the one carrying a briefcase. They met for an hour in the parking lot of a closed-down gas station across from the Gillette Company plant along the Fort Point Channel.
