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The Secret Life of Whitey Bulger
  • June 26, 2014 : 13:06
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By the time he retired, in 1990, John Connolly had received a distinguished service award, presented to him by then FBI director William Sessions. During his tenure with the Bureau, Connolly proved particularly adept at “flipping” ranking mobsters, getting them to roll over and snitch by providing vital secret information on organized crime. His FBI superiors ordered Connolly to cultivate top Irish gangsters as potential secret informers on the Italian Mafia. He was from the neighborhood and knew these guys from when they were kids, he was told, so why not give it a try? Through his old friend Billy Bulger, Connolly approached Whitey. As Connolly tells it, they arranged for a late-night meeting in a parked car overlooking Boston Harbor in September 1975.

In the car Connolly played Bulger a tape of a wiretapped phone conversation between Jerry Angiulo, head of Boston’s arm of La Cosa Nostra, and a Mafia hit man. Angiulo had put out a contract to have Bulger killed. Bulger thanked Connolly for the tip, but he declined to help the FBI. He went back and talked to his partner Stephen Flemmi, a killer in the Winter Hill gang, and learned that the Rifleman had already signed on to the FBI’s top-secret program. Bulger changed his mind and entered the rarefied, treacherous terrain of the Top Echelon criminal informant program.

The Italians had a contract on his head, and Bulger allegedly said to Connolly of his rival mobsters, “If they want to play checkers, we’ll play chess. Fuck ’em.” According to Connolly, the deal he was instructed to make with the rising crime boss was simple and clear-cut: Give us the guineas and you and your Winter Hill mick gang get a pass.

From that day forward, Connolly and Bulger were bound together in a secret covenant. They were shadowed by a neighborhood code of honor that holds informers, rats, snitches as the lowest form of life. The secret interplay in that relationship is vital—if it becomes known, people die.

A November 1982 performance appraisal of Special Agent John Connolly for the rating period of November 15, 1981 to November 12, 1982 states, “[Special Agent] Connolly’s performance in this area [the Top Echelon informant program]…is truly exceptional. He independently has developed, maintained and operated a corps of extremely high-level and productive informants. His direction and their resultant information has [sic] brought about results exceeded by none in the Boston Division’s Organized Crime Program. Most significantly, he skillfully developed a high-ranking LCN [La Cosa Nostra] figure who is presently the only member source in New England and one of very few developed since enactment of legislation dealing with organized crime nearly two decades ago. His performance has been at the level to which all should aspire to attain but few will realistically reach.”

As FBI assets, Whitey Bulger and Stevie Flemmi were Connolly’s top performers. They supplied invaluable inside mob intelligence to the FBI for more than 15 years. That information often constituted the probable cause the feds needed to get warrants, plant bugs and mount wiretaps, which provided Department of Justice prosecutors evidence to indict and convict the entire hierarchy of the New England branch of La Cosa Nostra, the long indomitable Patriarca crime family, ruled by Mafia commission member Raymond L.S. Patriarca and later by his inept son Ray Junior.

As Connolly explains the Bureau’s rationale in using TEs, it was only through the use of highly placed criminal informers that the FBI was able to penetrate the executive level of the Mafia. “The FBI, unlike state or local police departments, is responsible by statutory authority for protecting the internal security of the United States,” Connolly says. “State and local law enforcement have no such statutory obligation from Congress. The FBI’s domestic investigative responsibilities include addressing the threat posed by the international criminal conspiracy known as La Cosa Nostra—the Mafia—which is another investigative responsibility state and local law enforcement do not have. The Bureau’s operational strategy of maintaining TEs to address the investigative mandate to bring down the Mafia was necessitated by statutory obligations the FBI was saddled with by Congress.

“The proof is in the pudding. The fact is, it was due in large measure to the probable cause furnished by my long-term TEs that allowed the Boston FBI office to degrade, destabilize and dismantle the New England Mafia in a series of highly publicized court-authorized wiretaps.”

Conceived by FBI honcho J. Edgar Hoover and first known as the Top Hoodlum program, the Top Echelon informant initiative is still in wide use today. In essence, the TE program gives informers protection from prosecution for whatever crimes they may commit as long as they continue to provide valuable information to their FBI handlers—and as long as they do not commit murder or extreme violence. However, the kind of informers these agents look to recruit—made members of organized crime, high-level dope dealers, members of violent terrorist cells—reach those lofty levels in their chosen field only by killing people. So the idea of the TE program is paradoxical, as perverse as the cross-dressing paranoid lawman who conceived it. Yet the program worked. It worked very well indeed. 

In the winter of 1981, guided by Special Agent John Connolly and with information provided by Bulger and Flemmi, the FBI placed bugs in the Boston headquarters of Patriarca underboss Jerry Angiulo. Recordings of the foulmouthed Angiulo ordering hits and berating underlings in his far-flung criminal organization resulted in the indictment and conviction of dozens of high-ranking Italian gangsters—Italian being the operative word.

Eight years later, in October 1989, Bulger and Flemmi gave the FBI the tip that led agents to place the wiretap that recorded for the first time a traditional Mafia induction ceremony, presided over by Raymond Patriarca Jr. The gangsters met in the basement of a home in suburban Medford, Massachusetts. Four new members took the blood oath to kill anyone who violated the organization’s rules. The tape and the transcript made from it were an unparalleled evidentiary bonanza for the feds. Prosecutors used the tape in a number of Mafia trials around the country to prove the existence of the secret criminal organization.

As the FBI shattered the Mafia’s criminal organization in New England, the path was clear for Bulger and his Winter Hill gang to seize total control. Working out of their headquarters—Triple O’s bar in South Boston and later a Lancaster Street garage in the shadow of tony Beacon Hill—Bulger now ran his criminal empire.

Although the deal the Department of Justice made with Bulger and Flemmi paid off, it had serious unintended consequences. People were murdered, and not only criminals. Girlfriends of criminals. Innocent people who got caught up in the cabal. Legitimate businessmen who unknowingly became involved with organized-crime figures.

TE informers are valuable only as long as their identity remains a highly classified secret. They are never required to testify at trial or wear a wire. The informers and their agent handlers walk a fine line between crime control and government-sanctioned criminal activity. The agent handlers need the intelligence provided by the informers in order to do their job and stay alive. In one case, dubbed Operation Lobster, an undercover FBI agent’s life was saved thanks to information provided by Bulger. All too often, however, the question becomes, Who is handling whom?

When he retired, Connolly took a position as head of security at Boston Edison. He resumed a normal family life with his wife and sons—hockey games in winter, summer vacations on Cape Cod. He didn’t miss the stress of handling a stable of violent, cagey criminal informants. Life was good.

Bulger, meanwhile, was planning his retirement—stashing money in safe-deposit boxes across the country and even in a London bank, acquiring false identification, driver’s licenses in dead people’s names, Social Security cards. And he was managing long-term relationships with three different women. Always with his finger on the quickening pulse of the heat, Bulger knew that with the changing of the guard in New England’s federal law-enforcement chain of command it was time to get out of town. He scooped up his main squeeze, a single mother named Teresa Stanley, and together they set off on a leisurely cross-country motor trip.

New assistant U.S. attorney Fred Wyshak had arrived in Boston with an agenda: Take down Bulger and Flemmi, even if it meant exposing the FBI’s secret TE program in the process. Wyshak teamed with prosecutor Brian Kelly, and soon they were making cases against low-level bookmakers and loan sharks, with their sights set on the Winter Hill gang’s bosses. The prosecutors called on Bulger and Flemmi’s former handler, who by then had already retired from the Bureau. When Connolly was told the prosecutors were investigating his TE informers for crimes including bookmaking and loan sharking, Connolly maintained that the FBI and higher-ups in the Department of Justice had given the informers immunity for “anything but murder.” Wyshak informed Connolly that that deal was now off the table. They were going to take down Whitey and his partner, the Rifleman.

The new regime in the Boston federal prosecutor’s office urged Connolly to go along with the program and deny there had ever been an arrangement with Bulger and Flemmi. Connolly was adamant: no deal. He refused to lie about the arrangement, which had been underwritten and ratified by his superiors, including the former U.S. attorney in Boston, Jeremiah T. O’Sullivan. If Connolly lied and Bulger went down, the former FBI man (not to mention his family) could find himself in Bulger’s crosshairs. Besides, Connolly says, both his direct FBI supervisor in the 1980s, John Morris, and O’Sullivan asked Connolly to arrange meetings for them with the crime boss. O’Sullivan and Bulger met in a Boston hotel room. Bulger and Flemmi went to dinner at FBI supervisor Morris’s suburban home, where they enjoyed a lavish wine-soaked meal together. Morris later admitted to taking cash and gifts from the gangsters. The fine line between cops and criminals became obscured. Their mandate: Do whatever it takes to bring down the Italian Mafia.

When the indictments against Bulger and Flemmi were unsealed in 1995, Flemmi was arrested in a restaurant he was renovating near Faneuil Hall in downtown Boston. But where was Bulger? He had vanished.

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read more: entertainment, News, issue december 2012


  • Anonymous
    John should not only be exonerated by whitey Bulger but also by the entire justice departments !! Great article
  • Anonymous
    I enjoyed the article but as a friend of "a young US Marshall zeroed in on the lead" I find it odd that Playboy didn't mention his name. Neil Sullivan was THE reason that Whitey Bulger was captured. The FBI was secondary to Neils' relentless work to apprehend a fugitive and his work should be noted.