Whitey Bulger — How He Beat the State Police

Whitey Bulger Batted 3 for 3 Against Massachusett’s Finest

Whitey Bulger Beats the Massachusetts State Police

In 1980, Whitey Bulger Was Clever Enough to Foil State Police Surveillance

How do you beat the oldest state-wide police force in America? Whitey knew how.

The Massachusetts State Police force was founded in 1865 and currently has over 2,000 officers. But in 1980, they struck out in their surveillance attempts against Whitey and his underworld partner Stephen Flemmi.

State troopers were tipped off about a repair garage on Lancaster Street serving as Whitey Bulger’s new business headquarters. It was located near the North End, home to Boston’s Italian Mafia. The state police rented space on the third floor of a building across the street from the garage.

Whitey Bulger Conducting Business at Lancaster St Garage

Whitey Bulger and Stephen Flemmi Meet With Mafia Lieutenant Nick Giso.

Day after day, they watched various figures from Boston’s underworld entering and leaving the Lancaster Street garage. Over a course of six months, they documented the traffic and took lots of photos. Enough to convince a judge they should be allowed to place bugs inside the garage.

The first attempt failed when the microphone planted by the troopers picked up random noises but no voices. Strike two was when they placed another mike inside a couch cushion in Whitey’s office. The new plan might have worked if the next person to sit on the couch wasn’t Mafia henchman Vincent Roberto. Known as “Fat Vinnie”, he weighed over 400 pounds.

Vincent "Fat Vinnie" Roberto

Mafia Henchman Vincent Roberto, nicknamed “Fat Vinnie”, squashes a hidden mike

When Roberto sat down, he crushed the microphone. What the troopers across the street heard in their headphones was something like the roar of the crowd in nearby Boston Garden when the Celtics beat the L.A. Lakers.

Other failures involved interference from radio signals, causing the microphones to pick up an unintelligible jumble of noise. When the troopers finally succeeded in planting a microphone successfully, Whitey and his colleagues stopped conducting conversations in the garage’s repair bays. Instead, they’d all climb into a car and shut the doors before talking business.

Whitey Bulger and Boston Mafia Boss Harry Angiulo

Mafia Boss Harry Angiulo (left) Discusses Business With Whitey Bulger (right) at the Garage

When the troopers at long last began to pick up conversations, their excitement quickly faded to embarrassment. The comments they heard all went something like, “You want to make sure you obey the speed limit. The Massachusetts state police are very good at catching people who break the law. They’re very, very good at what they do…”

It had gone on for months. And for all their hard work, the state police had nothing to show. Knowing that Whitey Bulger used a pay phone in front of a Howard Johnson’s restaurant in Dorchester to talk business, they sought permission to bug it. The very day that a court authorized the bugging of the phone, Whitey stopped using it.

Stephen "The Rifleman" Flemmi

Stephen “The Rifleman” Flemmi (State Police Surveillance Photo)

The state troopers tried one last time with a scheme to seize Stephen Flemmi’s car so they could install a secret micrphone inside. It failed when Flemmi flipped out, telling the troopers is was ridiculously clear they just wanted to bug his car because all their other efforts had failed.

The DEA proved equally unsuccessful. In 1984, they planted a bug in Whitey’s car, but he soon had a South Boston mechanic tearing apart his car door. Inside they found the bug. The DEA agents rushed to the shop to retrieve their expensive surveillance equipment. It was worth $50,000.

When the agents burst into the shop, Whitey greeted them with a smile. Holding one of the mike’s wires like a rat’s tail, he uttered his famous words, “Relax, we’re all good guys here. You’re the good-good guys. We’re the bad-good guys.”

Whitey’s quote revealed how he viewed his status with the federal government. He and Stephen Flemmi were both official FBI informants. As a result, Whitey believed he was working for the right side of the law. And that everything he did in the course of his business, no matter how crazy, was sanctioned by the government.

Whitey Bulger's Handler at the FBI Was Childhood Friend John Connolly

Special Agent John Connolly Was Whitey Bulger’s Handler at the FBI

It was their status as FBI informants that allowed Whitey and Flemmi to always stay one step ahead of other law enforcement agencies. They were often informed of secret investigations and pending arrests. The FBI would have been aware of the state police surveillance in 1980, and Whitey and Flemmi were almost certainly being tipped off by Agent John Connolly.

Connolly grew up in South Boston and was a childhood friend of Whitey’s. It was Agent Connolly who tipped off Whitey and Flemmi in 1995 when they were about to be indicted. The warning allowed both men to flee, and extended Whitey’s federal holiday until just last year. Agent Connolly was convicted in 2002 for racketeering and obstruction of justice related to his relationship with Whitey and Flemmi.

(This post authored by Steve Burke)

Steve Burke

To read more about how Whitey Bulger beat the state police at the surveillance game, check out a good article in the Boston Globe’s Spotlight series: The Bulger Mystique.

Another in-depth article by the Boston Globe gives great insight into Whitey Bulger’s relationship with the FBI. 

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