How Whitey Bulger Bought Boston
William Norman Grigg
Recently by William Norman Grigg: When
the State Breaks a Man
Brothers Bulger: How They Terrorized and Corrupted Boston for a
Quarter Century, Howie Carr, Warner Books, 342 pages
was a woman of small skills and modest ambitions. Just before Christmas
in 1980, two men broke into the single-family home Peggy shared
with a live-in boyfriend in southwest Dade County. The intruders
threw a rope around the boyfriends neck and hanged him near
the front door. They then grabbed Peggy, shoved her against the
kitchen sink, draped a noose around her neck, and began feeding
the other end of the rope into a garbage disposal.
With the rope
tight enough to terrify the victim without rendering her unconscious,
the assailants turned off the grinder and began asking the terrified
woman about her work as a cashier at the Miami fronton
(or arena) of World Jai Alai, an exotic Iberian sport that had been
controlled by Bostonians since the 1920s. A few months earlier,
World Jai Alai had been sold to a new owner, and Bostons Winter
Hill mob led by James Whitey Bulger wanted
to know if the new owners had discovered the mobs skimming
operation. Satisfied by Peggys panicked answers, the invaders
flipped the switch on the disposal.
the cops found the two bodies the next day, notes Boston
Herald columnist Howie Carr in The Brothers Bulger, they
chalked it up as another Miami drug deal gone bad. In fact,
it was just one of scores of murders committed by a Boston crime
combine that wedded the Irish mob to the FBI. That marriage eventually
broke up in 1996, when Bulger tipped off by his FBI handler,
John Connolly fled the United States one step ahead of several
murder indictments. He is presently number two on the FBIs
Most Wanted list, below another one-time asset of the federal government
named Osama bin Laden.
of various racketeering charges, is in prison until at least 2010.
He also faces first-degree murder charges in Florida for allegedly
providing information that led to the murder of Peggy Westcoats
one-time boss, World Jai Alai president John Callahan.
At the time
of Peggy Westcoats murder, the head of security for World
Jai Alai was retired FBI Special Agent H. Paul Rico. Rico had taken
note of Whitey Bulger in the early 1950s, when the future head of
the Irish mob was a small-caliber hoodlum working as a homosexual
prostitute. Rico, writes Carr, could justify his sojourns
to the Bay Village gay clubs as reaching out to new sources.
From the very
beginning of his career as a South Boston thug, Bulger was an informant.
Gangsters planning to hijack a truck might mention something
about a future score to Whitey, just in passing, and sure enough,
when they showed up to grab the truck, the FBI or the local cops
would be there waiting, Carr recounts. H. Paul Ricos
personnel file soon included commendations from the director, J.
Edgar Hoover. At the same time, no one suspected Whitey it
was inconceivable that one of Southies own would become a
Sent to prison
in Atlanta for bank robbery in 1956, Whitey volunteered to serve
as a test subject in LSD experiments in exchange for time off his
20-year sentence. We were recruited by deception, Bulger
later complained, recalling that he was supposedly helping find
a cure for schizophrenia. Dr. Jules Pfeiffer, who supervised
the experiments, was working off a grant provided by the CIA, which
probably wasnt interested in humanitarian applications of
to Southie in 1965, just in time to benefit from three critical
developments. First, the FBI in keeping with Robert Kennedys
priorities had decided to tear into La Cosa Nostra (better
known as the Mafia). Special Agent Rico thus began to cultivate
informants and allies within the Winter Hill mob, the Mafias
days before Whiteys return, one of Ricos informants,
Jimmy The Bear Flemmi, murdered an undistinguished thug
named Edward Deegan. In order to protect their informant, the Boston
FBI office conducted a cover-up, sending four admittedly unsavory
men to prison for Deegans murder, which they didnt commit.
By collaborating in that murder and cover-up, the Boston FBI office
effectively made its bones as a full-fledged ally of
the Irish mob.
But for Whitey
Bulger the most propitious development was the emergence of his
younger brother Billy as a rising political star in Bay State politics,
which Carr describes as seamlessly integrated with the underworld.
In 1961, when
the Kennedy family entered the White House and Billy Bulger made
his debut as a state legislator, the informal rules of conduct on
Beacon Hill boiled down to three points: Nothing on the level;
everything is a deal; no deal [is] too small, writes Carr.
Massachusetts novelist Edwin OConnor describes state politics
as a special kind of tainted, small-time fellowship
through which even the sleaziest poolroom bookie managed,
in some way, however obscure, to be in touch with the mayors
office or the governors chair.
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Norman Grigg [send him mail]
publishes the Pro
Libertate blog and hosts the Pro
Libertate radio program.
© 2011 The American Conservative
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