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How Whitey Bulger Bought Boston

The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century, Howie Carr, Warner Books, 342 pages by William Norman Grigg | June 23, 2011 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 […]

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

by William Norman Grigg | June 23, 2011

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.”

Billy Bulger would eventually become president of the state Senate, a post that allowed him to dispense patronage as he saw fit. Boston-born FBI agents like Paul Rico, who confronted mandatory retirement at 50, were eager to cultivate Billy Bulger’s favor. By racking up arrests of Italian mobsters, the G-men could earn promotions and plaudits. By taking care of the Bulger family, they could supplement their federal paychecks and maybe arrange cushy post-retirement sinecures at Boston Edison or some other hack habitat.

Before leaving Boston for Miami in 1970, Rico recruited Steve Flemmi, a close associate of Whitey Bulger who was also tied in with the Italian mob, as a “top echelon informant.” Five years later, Whitey—who had by then established himself as a secure but unremarkable racketeer—was also granted “top echelon” status. Flemmi would scrape up intelligence on the Italians, and Whitey would pass it along to the feds. As Flemmi later described it, this relationship produced a perverse alchemy: “Me and Whitey gave [the Feds] sh-t, and they gave us gold.”

Why was Whitey included in this package deal, when Flemmi was the one with the mob contacts? As Carr points out, the Boston FBI office “didn’t need Whitey nearly as much as they needed his brother Billy”—and the favors that Billy could dispense on those who took care of his interests, including Whitey.

By 1980, Whitey, Stevie, and the FBI “were partners,” notes Carr. “And from the beginning, it was a one-sided deal. Each side would do ‘favors’ for the other, but the FBI’s were a lot more valuable than the cash and gifts that Whitey and Stevie would pass on to their agents.” Whitey and his handler, Special Agent Connolly, had grown up a few blocks apart from each other. They both wanted to take down Boston’s Italian mob—Connolly because doing so was the key to promotion within the bureau and Bulger because he wanted to clear the field of any rivals.

Connolly, who has tried unsuccessfully to sell a screenplay lionizing himself as the man who took down the Boston branch of the Mafia, has described his entente with Bulger as a brilliant “business” strategy—protecting one mob chieftain to take down scores of others. But that business arrangement was nothing less than a license for Bulger and his cronies to murder, extort, and rape with impunity. They also seized control over the local narcotics trade even as Bulger was heralded in the Boston Globe as a kind-hearted Robin Hood who was “keeping drugs out of Southie.”

In his own memoir, Brutal, one-time Bulger henchman Kevin Weeks observed of Whitey that while “nothing seemed to relax him or feel quite so good as a murder,” he was “calculating” and disciplined in killing. Flemmi, on the other hand, “would kill someone, anywhere, anytime.” Bulger and Flemmi were also incorrigible pederasts, the latter indulging a taste for underage girls, the former preying on children of both sexes.

Weeks also claims that Connolly and his corrupt fellow agents did more than merely look the other way. He asserts that Bulger “had six [agents] he could call on anytime and they would willingly hop in the car with him with the machine gun.” Being on the take was quite profitable for Connolly. A former secretary testifies that she once saw no fewer than ten uncashed federal paychecks in Connolly’s desk—a potent illustration of the contempt he felt for the substantial if unspectacular wages paid to an honest G-man.

While Connolly and his ilk were living large, honest Southies were living in terror. Carr and Weeks both describe the plight of Steve “Stippo” Rakes, a Southie who in 1983 scraped together enough money to buy a small piece of commercial property that he turned into a liquor store—the only one on Old Colony Avenue with convenient parking. As Rakes’s store began to prosper, anonymous death threats came spilling from his telephone. He soon fell prey to a Bulger protection racket and was forced to sell his business on concessionary terms. Renamed the South Boston Liquor Mart, the pilfered business soon became a favored hang-out of Bulger’s political allies.

During the 1987 Christmas season, relates Carr, “agents of the Boston FBI office bought the booze for the annual holiday party at the South Boston Liquor Mart. For the FBI the price was always right.” At John Connolly’s retirement party three years later, after the corrupted agent had heaped praise on Billy Bulger for getting him his job at the bureau and arranging his post-retirement gig at Boston Edison, he was handed a bottle of wine he was told came “courtesy of South Boston Liquors.” “No finer liquor store in the commonwealth,” replied Connolly with a knowing smirk.

What of Steve Rakes, who had that liquor store stolen from him by the FBI’s “top echelon informant”? Summoned to testify before two grand juries, Rakes—who had a wife and two daughters to protect—refused to talk. He was eventually convicted of perjury and sentenced to probation. Facing destitution, Rakes sought out a hack job with the Massachusetts Bay Transportation Authority. A friendly politician arranged one for him—in exchange for a $3,000 bribe.

“Absent justice,” wrote Augustine in The City of God, “what are kingdoms but vast robberies?” The unfathomably corrupt union of the criminal underworld and political “overworld” described by Carr offers a compelling illustration of what Augustine had in mind.

William Norman Grigg is the author of four books and Senior Editor of The New American magazine.

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