AFTER A WHILE, they called themselves “The Losers” -- this bunch of state troopers who spent 1980 trying to bust Whitey Bulger, only to suffer a series of bellyflops.
They bugged his office, the phones he used and, finally, tried to bug his car, but each time Bulger eluded them; he either uttered small talk or nothing at all.
The troopers had stumbled onto the Irish mobster by accident; a tip came in that a stolen car ring was working out of a garage near Boston Garden. Instead of stolen cars, the troopers found Bulger and his partner, Stephen Flemmi, were holding court daily inside the Lancaster Street garage.
Setting up shop in a Merrimac Street flophouse across from the garage, the troopers began keeping an eye on Bulger. To pass the hours while waiting for their target to appear, the troopers killed cockroaches, then mounted them on the wall, noting their size and time of death. From a third-floor window, they monitored what was suspected to be Bulger’s gaming and loan-sharking affairs.
The troopers captured the comings and goings of some of Boston’s best-known drug traffickers, loan sharks and hit men. “We saw the transfer of cash from hand to hand,” a trooper said. One day they tailed a Mafioso carrying a bag of cash from Lancaster Street to the nearby headquarters of Gennaro Angiulo, the Mafia underboss.
The stakeout was fruitful; six months of photos and intelligence was more than enough for a court to permit the troopers to plant a bug inside the garage. But as soon as they tried to close in on Bulger, the probe that had seemed so promising fizzled quickly.
First came the agonizing setbacks resulting from their own inexperience. The trick was breaking into the garage to install the bug. One break-in that succeeded involved a trooper hiding beneath the floor of a van that had been stored at the garage overnight. It became known as the Trojan Horse maneuver. Bathed in perspiration, the trooper climbed out in the early morning darkness and installed the bug. But the effort went for naught when the microphone failed to pick up voices.
Follow-up break-ins to move a new microphone into better listening positions also encountered technical troubles. Putting the mike under an office couch proved a disaster when Vincent (Fat Vinnie) Roberto, a reputed Mafia associate, sat his 400-pound frame down and squashed the bug; over the monitor, it sounded as if a hurricane had hit. Then the monitor failed to filter out radio transmissions. “We’d hear all the comings and goings of the ambulances across the city, it was terrible,” said a trooper. “Whitey would be in the middle of a sentence and all you’d hear is, ‘Unit 10, you’re needed at BCH.’ “
In the end, they listened in for about 30 days, but right off the troopers sensed Bulger was onto them. “Once we installed the device, all the conversations that were taking place in the open bays stopped,” said one official. “All of a sudden, in the middle of the summer, they start having people get into cars to have talks.”
And the talk they overheard was not the stuff of criminal cases. One time, Bulger rambled on about how he hated the television show “The Rookies”
because the Irish cops were portrayed as fools. The gangsters constantly listened to radio station WEEI and, “Whenever they’d hear a story about a crime, they’d stop and discuss the social significance of it. They’d be saying, ‘You can’t walk the streets anymore. . . it’s terrible how bad the crime is.’ We’d be rolling on the floor laughing.”
When one gangster told another who was going on vacation to be careful not to drive improperly “because those state troopers out there, they do a great job, they don’t miss a trick,” the troopers suspected something was amiss.
Then Bulger began showing up less, so the troopers, convinced he knew about the bug, tailed him. For three months, they watched Bulger and Flemmi make calls from the pay phones outside Howard Johnson’s in Dorchester. But that autumn, as soon as they bugged those phones, Bulger became a no-show.
”The day we were authorized to turn on at the pay phones, they stopped going there,” said a trooper.
As a last resort, they tried to put a bug into the car Bulger and Flemmi drove. The car’s alarm sent the troopers scrambling. A second attempt -- involving a ruse in which troopers would act as if the car was stolen, tow it away and then install a bug -- collapsed when Flemmi threw a fit at the trooper who pulled him over, shouting that their ploy to bug the car was obvious.
In less than 12 months, three swings, three misses.
Three years later, the Drug Enforcement Administration got in on the act. During drug probes in 1983, the agency kept bumping into Bulger’s ghost. ‘’Whitey’s name always came up in one respect or another,” said one official.
”Consistently you would hear the stories that they (traffickers) operated out of the piers of South Boston and that they were operating with Whitey’s sanction and would have to pay him some money through some of his people.”
By mid-1984, after months of careful planning, DEA agents inserted a bug in the windowsill of a condominium where Bulger was living in Quincy, the Louisburg Square complex. Mostly, all they got was a television blaring.
The drug agents, however, did succeed where state troopers had failed: They managed to hide a listening device in the panel of Bulger’s car door. Instead of a TV, agents heard a car radio.
”He would not talk to anybody unless the radio was blaring,” said an investigator who worked on the case.
But Bulger’s apparent genius for evasive action did not end there; not long after the bug was installed Bulger drove his car into a South Boston garage and ordered a mechanic to take the door apart. They found the tiny microphone, forcing agents to rush over to retrieve the government equipment.
”We got everybody else we wanted to, except Whitey,” noted a federal official.