The judge approved an extension, and the troopers, their hopes waning, devised their most ambitious plan. A trooper would stop Flemmi for a phony traffic infraction. The trooper would run Flemmi’s plate, inform him the Chevy had been reported stolen, and then order the car towed away. With the car in their possession, the troopers could install a bug before Flemmi retrieved it.

The trooper, Billy Gorman, stopped Flemmi one afternoon as he drove the Chevy through an intersection in Roxbury. Hidden but nearby, Long and the other troopers watched and monitored the cruiser’s radio. Gorman had been handpicked for the assignment; he was unflappable, and the mission called for a trooper who would not be drawn into an ugly exchange with the volatile gangster.

The cruiser’s lights flashed, and Flemmi pulled over. The trooper got out, and so did Flemmi. They headed for each other right there in the street. The trooper spoke first: “Did you see that old lady there you almost ran over?”

The many months of only being able to study gangster body language now ended abruptly, and at long last the troopers finally heard actual noise from one of their targets. Flemmi’s first words were hardly pleasant ones.

“What the fuck is this shit?” he shouted. No ordinary citizen, the gangster was not impressed by a trooper’s uniform and badge. His temper raced from zero to sixty in an instant. “Do you know who I am, you fuckin’ jerk? This is harassment!”

Methodically, Gorman asked Flemmi for his license and registration. “I don’t got no fuckin’ registration,” Flemmi yelled. “These are dealer plates, can’t you see?” The trooper calmly told Flemmi he should still have a registration. The trooper explained he was going to have to run the plate and that Flemmi would have to wait patiently. Gorman headed back to his cruiser, and Flemmi stormed off into a convenience store where he began making telephone calls.

In the cruiser Gorman consulted with Long. The tow truck was summoned. The installation crew was waiting in the back lot of the nearby abandoned Mattapan State Hospital. Flemmi came back out of the store, and Trooper Gorman explained that the car had been reported stolen. Gorman and Long even play-acted on the cruiser’s radio, with Long telling the patrol trooper, “Please be advised that the vehicle comes back as stolen from Nassau County, New York, in July 1979.” Gorman told Flemmi the Chevy was going to be towed.

Flemmi was apoplectic. Then he uttered the words that made Long’s and every other state trooper’s stomach turn to mush. “You tell fuckin’ O’Donovan that if he wants to bug my car so bad, I’ll drive it right up to fuckin’ 1010.” “O’Donovan” was obviously Lieutenant Colonel John O’Donovan, Long’s commander, and “1010” was a reference to state police headquarters. Flemmi knew.

It was over.

Flemmi went back inside the convenience store. The car was towed away, but even before its arrival behind the hospital Flemmi’s lawyer was telephoning O’Donovan screaming about the blatantly absurd seizure of the car. The state police commander kept a stiff upper lip and didn’t give the lawyer anything, saying the car had come back as reported stolen. But the troopers all knew the ruse was up. Long told the troopers not to even install the bug. Don’t give Bulger and Flemmi the satisfaction of taking apart the car and finding the bug, he said. Let them wonder, maybe they’ll get a little paranoid.

This was the troopers’ only consolation. They’d thrown the Hail Mary, and it had fallen woefully short. Despite their many months of successful surveillance, they’d lost in the streets against Bulger and Flemmi. They may have seen Bulger and Flemmi joined at the hip to the Boston Mafia, but they would not be taking them to court. They’d been outmaneuvered at every turn. But even in failure the state police had triggered, unbeknownst to them, a massive internal crisis over at the FBI, a crisis that, more than any other in the FBI’s long history with Bulger and Flemmi, posed the biggest threat to the cherished deal Connolly and Morris had with the two gangsters.

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CHAPTER SEVEN

Betrayal

Responsibility for the stunning breach in security in the potentially devastating state police bugging of Bulger and Flemmi fell squarely in the FBI’s lap, and on one agent in particular. “It was Connolly,” Flemmi later admitted. But Connolly wasn’t the only FBI agent watching out for Whitey Bulger like a lifeguard monitoring shark-infested waters. Morris, Flemmi added, had also tipped them off. The supervisor, said Flemmi, had told Bulger that another agent had come to him looking for background information on the two gangsters. Morris interpreted the inquiry as groundwork for another group’s plan to launch electronic surveillance.

In fact, before he heard from Connolly and Morris, Flemmi had gotten an even earlier tip about a possible bug from one of the bookies he and Bulger were in business with. The bookie claimed to have picked up his information from a state police trooper. But Flemmi was the first to acknowledge that this was second-hand, underworld hearsay that could not compare to the solid confirmation Connolly soon provided. “His job was to protect us,” said Flemmi about Connolly’s help.

Years later Connolly would finally admit that he warned Bulger and Flemmi, but his version came with a self-preserving twist: he claimed O’Sullivan had asked him to alert his informants. Flemmi, in court testimony, backed up Connolly. “Jeremiah O’Sullivan told John Connolly . . . [we] were being bugged down at Lancaster Street and to provide us with that information.”

O’Sullivan’s camp has denied Connolly’s version, a strained account that did not square with the prosecutor’s passion for putting gangsters behind bars or his animated enthusiasm for the state police operation in his meetings with troopers. Flemmi’s testimony was simply seen as a bid to protect the agent who for years had protected him. The more likely scenario, according to state police, was that O’Sullivan may have taken Connolly into his confidence out of professional courtesy—mindful that Connolly was in fact the FBI’s handler of Bulger and Flemmi—and that Connolly then betrayed that confidence. Indeed, the state police’s long-held suspicions of FBI duplicity hardened into dogma when one of the troopers doing surveillance spotted Bulger sitting with Connolly in a car in South Boston. Whatever the fine details, Morris and Connolly had warned Bulger and Flemmi, and the FBI leaks had undermined another police agency’s bid to target Boston’s Irish gang.

But amid the Morris and Connolly cover-up, there was one potential bright spot. O’Donovan had found an earnest audience in the one agent who counted—the new FBI boss in town, special agent in charge Lawrence Sarhatt, who did not buy Morris’s defensive explanations. They didn’t sound credible, and the more Sarhatt thought about it, the more he began asking a question far more threatening. Sarhatt wondered whether Bulger had become more trouble than he was worth. Had this South Boston gangster grown too close to his FBI handlers? Beyond the question of the leak, Sarhatt began asking Morris and Connolly about Bulger’s “suitability.” This whole new line of inquiry further jeopardized the core deal established by Connolly five years earlier.




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