Crime Library: Criminal Minds and Methods

James 'Whitey' Bulger

A Man of Contradictions

The dining room table groaned under the weight of the spread prepared for the evening: cold cuts, olives, cheeses, big bowls of pasta and salad, meatballs and sausage, bottles of fine wine, imported beer, and champagne. It was a grand Italian feast even though it was taking place in a house in South Boston, more commonly known as "Southie" to the locals, the city's staunchly Irish enclave. The guests were all men; the only woman in the house was the host's mother, who cooked and served the food. The group included local FBI agents, the President of the Massachusetts State Senate, and two of Boston's deadliest gangsters, Stephen "The Rifleman" Flemmi and his partner, the infamous boss of Boston's Irish mob, James "Whitey" Bulger.

Stephen J. Flemmi
Stephen J. Flemmi

In the late 1970s and early 1980s, celebrations like this were regular affairs for most of these men. Flemmi hosted this one at his parents' home. The prominent politician was Whitey Bulger's little brother, William "Billy" Bulger, who had been elected President of the State Senate in 1978. Billy Bulger lived directly across the street from Flemmi's parents. Though the brothers had followed radically different career paths, they were still family and remained close.

James J. "Whitey" Bulger
James J. "Whitey" Bulger

As usual the master of ceremonies for the evening was John Connolly, the flashy FBI special agent who served as Whitey Bulger's official handler. Both Bulger and Flemmi were enrolled in the FBI's Top Echelon Informant Program, which had been set up to encourage criminals to help the FBI arrest and convict more dangerous criminals. Also on hand that night was Connolly's boss, John Morris, the Boston office's Organized Crime Squad Supervisor, as well as several other special agents. The guests were all high-caliber power players, but the recognized "chairman of the board," according to Dick Lehr and Gerard O'Neill in their book Black Mass: The True Story of an Unholy Alliance Between the FBI and the Irish Mob, was, as usual, Whitey Bulger. Billy Bulger was well-known for his extraordinary oratorical abilities, and Connolly possessed the legendary Irish "gift of gab," but it was Whitey who held the floor, whether he was talking about his experiences as an inmate at Alcatraz, what it was like taking LSD for the government, or just shooting the breeze about nothing in particular.

Black Mass
Black Mass

While the other men refilled their glasses freely, Bulger confined himself to a single glass of wine. He drank alcohol sparingly, didn't smoke, and worked out fanatically. He looked down on people who drank excessively and used drugs. Physically Bulger wasn't a big man -around 5'8" and 155 pounds - but he was one of the most feared men in Boston. He was a man who thrived on contradictions, most notably his relationship with the FBI.

FBI logo
FBI logo

Under the FBI's wing as a prized TE (Top Echelon Informant), Bulger became Boston's top organized crime boss, more powerful than even the Mafia. Bulger and his FBI handlers orchestrated the crippling of the local mob family, which allowed him to take over a large chunk of the Boston rackets. Murders would accumulate under his reign, 18 in all. With the FBI clearing the field for him, he expanded his operations in loan-sharking, drug dealing, extortion, and money laundering, mimicking what the Mafia had done before him. For over 20 years, the FBI looked the other way when it came to Bulger, and whenever they learned that other law-enforcement agencies were investigating their old pal Whitey, they gave him a heads-up.

With unusual cunning and intelligence and a predator's instinct for survival, Whitey Bulger ruled the Boston underworld from the late seventies to the mid-nineties. Thanks to his guardian angels at the Boston office of the FBI, he had a long and violent run.


Note: Originally published in 2004.

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