Whitey Bulger — How He Beat the State Police

Whitey Bulger Batted 3 for 3 Against Massachusetts’ Finest—the State Police

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.

The State Police Play a Waiting Game

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…”

More Bugging Attempts Fail

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.

Next at Bat: The DEA

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

FBI Tips Keep Them One Step Ahead

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. 

Read Another Post — Whitey Bulger — How He Shipped Arms to the IRA

Whitey Bulger — How He Terrified Mayor Kevin White

Remembering Kevin White

Boston and Its Busing Problem — An Irish Family Feud

Home Page — The Chieftains of South Boston

Whitey Bulger — How He Terrified Mayor Kevin White

Whitey Bulger Terrified Mayor Kevin White

Kevin H. White, Mayor of Boston 1968–1984

Fear Was Whitey’s Greatest Weapon Against Mayor Kevin White

Even in 1975, Whitey Bulger had enough of a reputation to put the fear into Boston’s leading political figure — Mayor Kevin White. So much so, that the mayor was frightened out of his wits one night when leaving his gym in South Boston. Afraid that Whitey or one of his thugs would be waiting to kill him in the dark parking lot.

Mayor White admitted as much in a 1978 interview with WGBH TV’s Christopher Lydon. “I was never more scared in my life,” White said,  “…Whitey would be crazy enough to do it. And if they shoot me, they win all the marbles.”

Why was the mayor so afraid of Whitey Bulger? And why would Whitey want to kill him?

This was during school desegregation. Also known as forced busing, it had turned the whole city of Boston upside down. During desegregation, tempers were especially high. There were lots of protest marches, lots of violence and plenty of resentment.

Whitey Bulger In a Surveillance Photo With Stephen Flemmi and Kevin Weeks

Whitey Bulger With Colleagues Stephen Flemmi and Kevin Weeks On Castle Island in South Boston — DEA photo by Special Agent Mike Swidwinski.

Whitey Bulger’s Business Disrupted by Desegregation

South Boston was at the center of the storm. As the buses rolled into town, so did lots of cops. As a South Boston resident, Whitey Bulger was just as resentful as everyone else in his community. He also resented the police presence because it made it more difficult to conduct his business on the streets.

At the time, Whitey was part of a merger of different gangs, the Mullens, the Killeens and Winter Hill. To the police, they were referred to as the “Irish Mafia.” (Read more about the history of the gangs, and how Whitey ended up on top, in this ShortList article.)

J. Anthony Lukas writes about the mayor’s concern that the gangs would infiltrate an anti-busing march in September, 1974. In his Pulitzer-Prize winning book Common Ground, Lukas says White feared the gangs would draw weapons and shoot at the police if the march was stopped. There were also reports that the gangs were passing out weapons to kids in South Boston so they could join the battle as well. One rumor had Whitey Bulger preparing to blow up all the bridges into South Boston to keep the buses out.

Senator William Bulger vs Mayor Kevin White in the Busing Crisis

During Busing, South Boston Senator Billy Bulger Was No Friend of Mayor Kevin White

Billy Bulger’s Political World Disrupted by Desegregation

Another reason the mayor was terrified was because of Whitey’s brother Billy Bulger. The senator from South Boston was a fierce opponent of busing and one of Mayor White’s biggest political adversaries. The two had a very tense relationship. Kevin White was certain that if he ever crossed Billy Bulger, the senator would call on his brother Whitey to punish, even kill, him.

There’s no evidence that Billy Bulger ever asked his brother to do such a thing. But the fear was real enough for Mayor White. In a 1992 Boston Magazine article, he talks about a night he was called to meet at senator Bulger’s house in South Boston. The meeting was to take care of political business. But all the way there, the mayor feared that Billy had called him to South Boston where Whitey Bulger could kill him more easily.

Kevin White survived the years of desegregation, serving as mayor of Boston until 1984. And he survived any threats, real or imagined, from Whitey Bulger. Succeeding White as mayor was Raymond Flynn, the first South Boston politician elected mayor of Boston.

(This post authored by Steve Burke)

Steve Burke

Read another post — Whitey Bulger — How He Shipped Arms to the IRA

Whitey Bulger — How He Beat the State Police

Remembering Kevin White

Boston and Its Busing Problem — An Irish Family Feud

Home Page — The Chieftains of South Boston