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?

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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.




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