James '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
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.
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.