The Mob-FBI Axis

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Recently by William Norman Grigg: When the State Breaks a Man


The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century, Howie Carr, Warner Books, 342 pages

Peggy Westcoat 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 boyfriend’s 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 Boston’s Winter Hill mob – led by James “Whitey” Bulger – wanted to know if the new owners had discovered the mob’s skimming operation. Satisfied by Peggy’s panicked answers, the invaders flipped the switch on the disposal.

“When 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 FBI’s Most Wanted list, below another one-time asset of the federal government named Osama bin Laden.

Connolly, convicted 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 Westcoat’s one-time boss, World Jai Alai president John Callahan.

At the time of Peggy Westcoat’s 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 Rico’s 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 Southie’s own would become a rat.”

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 wasn’t interested in humanitarian applications of the drug.

Whitey returned to Southie in 1965, just in time to benefit from three critical developments. First, the FBI – in keeping with Robert Kennedy’s 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 Mafia’s deadly rival.

Second, just days before Whitey’s return, one of Rico’s 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 Deegan’s murder, which they didn’t 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 O’Connor 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 mayor’s office or the governor’s chair.”

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William Norman Grigg [send him mail] publishes the Pro Libertate blog and hosts the Pro Libertate radio program.

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