For years, one of America's most wanted men, Whitey Bulger, lived free while a high-level FBI agent suspected of conspiring with him took the fall and rotted in a prison cell. In 2008, Richard Stratton spoke to that former FBI agent, John Connolly, at a Florida correctional facility and found what appeared to be a miscarriage of justice. Even after Bulger's capture, Connolly remained locked up, but now a Florida appeals court has overturned his second-degree-murder conviction and he is expected to go free. Here's the full story from January 2009 issue of Playboy that tells how Connolly turned Bulger into an FBI informant and how the tables were eventually turned on Connolly.


Turner Guilford Knight Correctional Center, Dade County's main lockup, bakes in the hot sun of an asphalt desert near Miami International Airport. It's a cavernous, fortress-like jailhouse hosting 1,300 beds for male and female pretrial prisoners. I'm escorted by a lanky hack into the dirty bowels of the joint. Up one elevator, along drab corridors smelling faintly of disinfectant and despair, down another elevator, through a maze of hallways and past electronically operated gates into a video-monitored sally port. Finally we enter the Security Housing Unit—otherwise known as the Hole.

A cluster of keys jangling from the guard's belt reminds me of the irony of the moment: I am an ex-con turned writer and filmmaker who spent nearly a decade in some of America's most secure pris­ons, now entering freely behind bars to question an imprisoned former FBI agent. When the interview is over I'll walk back out into the south Florida sunshine; John Connolly, the highly decorated ex-agent, will return to his dark, narrow jail cell. Still, I shudder at the sound of the steel gates crashing behind me.

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Connolly shuffles into a cramped visit­ing area in shackles and chains, a law­yer's portfolio tucked under his arm. He has Celtic skin and clear blue eyes, and he's wearing a fire-engine-red jumpsuit that makes his jailhouse pallor seem all the more pallid. Otherwise he looks fit and strong for an ex-lawman in his mid-60s living in a dungeon.

"How long have you been in the Hole?" I ask as we sit in a steel-plated chamber on steel seats at a steel table bolted to the steel floor.

"Going on three years," he answers, adjusting the chains attached to his ankles. The leg irons strike me as correctional overkill—there is nowhere to run. "I was doing good when I was at the other prison, going outside, getting regular exercise. In here the big event of the day is when they shove a food tray through the trap in the cell door."

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Connolly retired from the FBI in 1990 after playing a pivotal role in decimating the New England branch of the Cosa Nostra. Much of his suc­cess as a Mob buster was due to the stable of top-echelon informants (TEs) he handled. In the ranks of FBI agents in the 1980s, Connolly was legendary for his ability to flip informants within powerful crimi­nal organizations. His most notori­ous informant was James "Whitey" Bulger, criminal mastermind and boss of the Boston Irish Mob known as the Winter Hill Gang.

Nineteen years later, in a dia­bolical reversal of fortune, Con­nolly is locked down 23 hours a day, six years into a 10-year federal sentence for racketeering and obstruction of justice—for supposedly tipping Bulger off to an imminent indictment so he could abscond. The former agent is also facing life in Florida for first-degree murder in a killing orchestrated by Bulger. (Since the time of our interview Connolly was convicted of second-degree mur­der for this killing, one he neither ordered nor witnessed.) Bulger, meanwhile, is in the wind, a fugi­tive traveling the world with his blonde girlfriend.

Connolly agreed to speak to me on the condition that I wouldn't question him about the Florida murder case. This is the first and only time since he has been locked up that he has gone on record about his close—some might say fraternal, blood-brother-like—relationship with Bulger. The United States justice system believes the bond went beyond that of agent and informant. After Connolly was con­victed in federal court in Boston, in 2002, U.S. Attorney Michael J. Sullivan announced, "He abused his authority and crossed the line from crime fighter to criminal. Today's verdict reveals John Con­nolly for what he became: a Winter Hill Gang operative masquerading as a law-enforcement agent."

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"Did you cross the line?" I ask Connolly.

"Absolutely not. I did my job, what I was ordered to do."

What is the line Connolly sup­posedly crossed? Where exactly is it drawn in the shadowy world inhab­ited by agents and informants, cops and crooks whose very lives are held tenuously in one another's hands? This much is fact: Sometime after Connolly retired from the FBI, the rules of engagement changed. Bulger and his partner, Stephen "the Rifleman" Flemmi, were indicted for gambling-related crimes they were allowed to commit in exchange for the information they fed to the FBI. Flemmi was arrested; Bulger was nowhere to be found. Thirteen years later he remains number two on the FBI's Ten Most Wanted list, second only to Osama bin Laden.

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"Where do you think Whitey is?" I ask Connolly.

"That's anybody's guess." he says. "I have no idea."

"But you knew him well. You had to trust each other with your lives. Why do you think the FBI can't catch him?"

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"Of all the TEs I had, Jim was without a doubt the most disci­plined and cerebral. He was a mas­ter of disguise going back to his bank-robber days. He could blend in anywhere, hiding in plain sight. He could be in Cambridge."

"Do you believe he's still alive?"

"I think we'd know if he were dead."

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"The girlfriend?"

"Catherine Greig, right. She would have come in. She's still a fairly young woman, mid-50s. No one wants to live indefinitely on the lam." Connolly considers for a mo­ment. "Jim is a health and physical-fitness enthusiast who takes very good care of himself. I have no rea­son to believe he's not alive."

Since he disappeared, in December 1994, Bulger has emerged as the most illustrious criminal folk hero of our time, surpassing even Colom­bian drug lord Pablo Escobar. He is the last of the great Irish gangsters, a Cagneyesque breed of charismatic killers who doted on their mothers, helped old ladies cross the street and handed out turkeys at Thanks­giving. Bin Laden aside, Bulger is the only Most Wanted fugitive with an FBI task force dedicated to catching him. On his 79th birthday, September 3, 2008, the feds dou­bled their reward, to $2 million. "I am confident he will be captured," said FBI special agent in charge Warren Bamford. Bulger is charged in a superseding indictment with 19 counts, including murder, con­spiracy to commit murder, racke­teering, extortion, conspiracy to commit extortion, narcotics distri­bution, conspiracy to commit money laundering, and substantive money laundering. If he is not caught and dies a fugitive, it will be the first time in the annals of American crime that a mobster of Bulger's stature has successfully eluded the long arm of Uncle Sam.

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Who is Whitey Bulger, and why can't the FBI catch him?

"Think Robert De Niro's character in the movie Heat, but with a sense of humor' is how Connolly describes his informant." We used to meet in the Public Garden, across from Boston Common, by the sculpture Make Way for Ducklings. Sometimes at night we'd walk along the Charles River Espla-nade, both of us wearing baseball caps pulled down to hide our eyes. No one knew who we were. Jim learned to survive in a world of justifiable paranoia."

Featured on America's Most Wanted more than a dozen times, as well as having at least 10 books written about him and a Showtime TV series called brotherhood based loosely on his life, not to mention the character played by Jack Nicholson in the Academy Award-winning movie The Departed. Bulger has become our most famous crook. Even Escobar with his coca billions was hunted down and killed by agents of the law.

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Bulger's no slouch when it comes to amassing a criminal fortune, either. Forbes.com recently estimated his bankroll at between $30 million and $50 million. On its wanted poster the FBI claims Bulger" is an avid reader with an interest in history. He is known to frequent libraries and historic sites. Bulger may be taking heart medica­tion. He maintains his physical fitness by walking on beaches and in parks with his female companion, Catherine Elizabeth Creig. Bulger and Creig love animals. Bulger has been known to alter his appear­ance through the use of disguises. He has traveled extensively throughout the United States, Europe, Canada and Mexico. Con­sidered armed and extremely dangerous."

The relationship between John Con­nolly and Whitey Bulger dates back to their childhood days in the Old Harbor housing project of South Boston. Of his Southie childhood, Connolly remembers, "What we lacked in material things proved inconsequential in comparison to the rich experiences and tapestry of everyday life glowing up there. Someone once made the point that those who didn't grow up in Southie were somehow impoverished.' Connolly was closer in age to Bulger's younger brother Billy, who was an over-achiever to the extreme. Connolly nev­ertheless came of age under the spell of the Whitey mythos. "I did have a couple of brief encounters with him when I was a kid," Connolly recalls. "But mostly I knew him by reputation as a hell-raiser who had the whole housing project in an uproar."

Bulger was simply the toughest, most charismatic, wildest kid in a vibrant and famously clannish hotbed of cops, poli­ticians, priests, fighters and criminals. Southie is as distinct physically as it is culturally and temperamentally. The pen­insula of South Boston juts out into the Atlantic like a left jab. In his 1990 memoir, While the Music Lasts, Billy Bulger says of his stomping grounds, "Our roots were local. They ran deep. They kept us from being merely a part of the whole. We valued our mélange of cultural traditions, and we had a shared sense of security. We w ere a neighborhood: an enclave so discrete that we sang 'Southie Is My Hometown' and referred to a trip into the central part of the city as 'going to Boston.'"

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From those tough streets they emerged: Billy Bulger, who became a "triple Eagle" graduate of Boston College High. Boston College and Boston College Law School, a local politician who went on to become head of the Massachusetts state senate and president of the University of Massa­chusetts; John Connolly, the lawman who would bring down the Italian Mob that for so many years rivaled the Irish Mob; and Jim, the infamous Whitey, who went off to the penitentiary in Atlanta while still in his 20s, after a conviction for bank robbery, and then to Alcatraz.

In the late 1950s and early 1960's, while locked up in Atlanta Federal Penitentiary, Jim Bulger volunteered for a project that was part of the CIA's covert LSD-testing program, code-named MK-ULTRA. He signed on as a guinea pig to ingest large doses of Sandoz LSD, the purest form of the drug in existence, administered by CIA-linked scientist Dr. Carl Pfeiffer in an ostensible effort to find a cure for schizophrenia. Over an 18-month period Bulger's reaction to the powerful psyche­delic was tested and recorded in exchange for a reduction in his sentence.

What happens when you take a person with a brilliant criminal mind, possibly a psychopath, give him huge hits of the most potent mind-altering substance known to man over a long period of time and then set him free? Whitey happened.

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When he left prison he returned to Southie to outwit, outmuscle or eliminate anyone who got in his way as he ascended to the top of a vast criminal empire. Dur­ing the deadly Irish gang wars in the 1960s and early 1970s, when Bulger took the neighborhood and indeed much of New England's underworld into his grip, Southie was like the Wild West. Bulger and his enemies were shooting it out in the streets, chasing one another with revolvers, blazing away with automatics and rifles. Men were gunned down at high noon in the middle of West Broadway. Or they were fired at by snipers perched on the rooftops of the three-story, redbrick Old Harbor and Old Colony housing projects, where most of the warring gang members went home to their families at night. No one said a word or saw a thing, not even when a man had his throat cut and bled to death behind the wheel of his Cadillac parked at a busy intersection.

By all accounts Bulger was a changed man when he returned from his nine-year bid in America's toughest joints. He worked hard at his craft. He was a voracious reader who studied military history and the art of war. He quoted Machiavelli and Sun Tzu. Home base was a bar called the Triple O's on West Broadway near the intersection of Dorchester Avenue (it has since been replaced by a bar called 6 House). Bulger made collections from local bookmakers and loan sharks—and put a beating on deadbeats who didn't pay up on time. He worked out daily to maintain his disciplined prison persona. In hard-drinking Southie, Bulger nursed an occasional beer. He kept his wits and reactions sharp as he dodged bullets from rival gang members.

Whitey's younger brother Billy says of him, 'Jim, I have always believed, had a quicker mind than mine and the intelligence to excel academically—had he wanted to." What Bulger wanted to excel at was crime, and he vowed he would never go back to prison.


How then could Bulger have become that most despised creature of the underworld: a rat, a cheese eater, a snitch—a law-enforcement informant? It went against everything the steely-eyed, lean and taci­turn ex-convict stood for, and it was anathema on the streets of Southie. "We loathed informers," writes Billy in While the Music Lasts. "It wasn't a conspiratorial thing—our folklore bled with the names of informers who had sold out their breth­ren to hangmen and worse in the lands of our ancestors."

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"How did it begin," I ask Connolly, "this special relationship between you and Whitey?"

"You've got to understand what was going on in the Bureau at that time." For years, Connolly explains, J. Edgar Hoover—the FBI's first director—had denied the Mafia existed. "Then after Apalachin, the 1957 Mafia summit in upstate New York that was interrupted by local cops, and with the Kennedy Justice Department in the 196Os, Hoover made it the Bureau's number one priority to go alter organized crime."

Part of that initiative was the Top-Echelon Informant Program. "We needed to develop sources, human intelligence, informants, to penetrate organized crime," Connolly says. A top-echelon informant, he explains, is defined as "a member of the Cosa Nostra or a close associate who is at the policy-making level of organized crime." The deal was a TE would never have to wear a wire or appear in court to testify but was expected to participate in ongoing criminal activity—"anything but murder"—so long as he continued to sup­ply the Bureau with valuable intelligence. "Of course," Connolly says, "the guy would have to keep working—committing crimes—or everyone would immediately suspect he was a rat."

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The mandate comes with a built-in con­tradiction: In order to make one's bones and become a made member of the Cosa Nostra or an organization like Whitey's Winter Hill Gang, a soldier would have to kill. "Did I know Bulger was a killer?" Con­nolly asks. "Of course I knew he was a killer. So did everyone else in law enforcement. Those were exactly the kinds of informants we were instructed to develop."

At one point, Connolly says, he had 20 TE's under his protective wing. "I liked them all," he says with a quick grin. He says he flipped Bulger in 1975. "When I was first asked by my supervisors to culti­vate Jim, I refused. I was too close to the family." But Connolly had information he-knew would be valuable to Bulger.

On a fall evening, with a harvest moon hanging over Boston Harbor, Connolly and Bulger met in Connolly's car parked at Wollaston Beach in Quincy. The agent laid it out for Bulger. He played him a tape of a tapped phone conversation between a notorious hit man and a Boston Mafia boss. The Italian Mob had decreed it was time that "Irish bas­tard " Bulger was taken care of.

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The Mafia was all about trading informa­tion, Connolly told Bulger, as if the savvy ex-con needed a primer on how the underworld operates. "Jimmy understood. At the highest level, that's just the way the game is played," says Connolly. Bulger had to trust Connolly and vice versa. Trust is the essential ingredi­ent of the TE- agent relationship. "Snitches gel outed and get killed," says Connolly. Bulger had to believe Connolly would protect him or else there would be no deal.

Bulger told Connolly he would think about it. A few weeks later they met again. It was a covenant made in the slippery back alleys of the underworld, between a Harvard-educated FBI man and a master-criminal graduate of Alcatraz, the Harvard of penitentiaries. They shook hands. Bulger joined the team and outplayed them all.


Just how powerful was Bulger? I found out when an upstart wise guy named Michael "Mickey" Caruana summoned me to a sit-down at a restaurant in Boston's North End. "The name's Caruana,' he introduced himself. "Rhymes with marijuana." It was the mid-1970s, and I was 30 years old. Those were the glory days of the so-called hippie Mafia's dominance of the booming dope trade. I had come of age with the business, from smuggling a few kilos of Mexican weed across the border as an Arizona State University freshman to importing multi-ton loads of primo hashish by sea and air. When the multi­million-dollar deals started going down, the real criminals made their move.

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Caruana said he had been given per­mission from New England Mafia don Raymond Patriarca of Providence, Rhode Island, a member of the rul­ing Cosa Nostra commission, to take over the lucrative pot trade on the East Coast. Caruana tried to shake me down for a million dollars, "for protection." I was paying off air­freight handlers at Boston s Logan Air­port to clear ship­ments of hash from Beirut without pass­ing through customs. Caruana wanted to cut himself in for half of my smuggling operation.

I respectfully declined the mafioso's offer, explaining I was already giving the Leba­nese a third, and when the airfreight people got their piece, if 1 gave Caruana half. I'd be losing money. As for the million for protec­tion, I said thanks, but I was going to pass.

A few days later 135 kilos of blond Leba­nese hash landed at Logan, and we got it out without giving Caruana a gram. Not long after, I got a call from a Caruana henchman, John Zullo, a ferret-like killer who would hide in the bushes outside your home and shoot you in the head as you unlocked your door. "I'm gonna cut your balls off and shove 'em up your mother's cunt! " Zullo said. "Then I'm going to kill you."

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For the first time in more than a decade as an outlaw I started carrying a gun. When my connection at Logan heard the wiseguys had put a contract out on me, he said it was time I was introduced to the boss. I met Bulger twice, both limes in a rear office of a Back Bay real-estate broker. "Hi, how ya doin'?" Bulger greeted me, and we shook hands. "I understand you got a problem with Mickey Caruana."

He was wearing a black leather jacket, shades, jeans and sneakers. The bright blond hair that had given him the nick­name Whitey was thinning. When he took off his sunglasses I saw the icy blue eyes.

"Don't worry about it," he told me when I explained what had gone down. "I'll straighten out Caruana.'

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In a rendezvous at a Hojos on the Southeast Expressway that was surveilled by Massachusetts State Police and agents from the Drug Enforcement Administra­tion, Bulger met with Caruana. The con­tract Caruana had given Zullo to kill me was lifted. I put my gun away.

"Just keep taking care of my guys at the airport," Bulger told me when I met him again to thank him. "You're a good earner, kid. I checked you out. If there's anything else you need, let me know.'

That's how powerful Bulger was: Even the wiseguys were afraid of him. If anyone had told me then Bulger was an informant for the FBI, I would have said, "You're out of your fucking mind."

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Eight years in prison cured me of my pen­chant for crime. Prison did the opposite to Bulger. We think of men like him and his ilk as aberrations, monsters. And they are. We are fascinated by them and repelled because somewhere deep down we know they are our creations, our brothers, our sons, our fathers, and had circumstances been differ­ent, we could have become them.


Kevin Weeks knows Whitey Bulger as well as anyone except perhaps Bulger's long­time live-in girlfriend, Teresa Stanley, and his current girlfriend-on-the-run, Cath­erine Greig. Weeks was one of Bulger's lieutenants (he has been called Bulger's surrogate son). "I was with Jimmy some­times 24-7 for weeks at a time," Weeks says. We are in Southie, sitting in a back room at the Rotary deli, which Weeks once owned with Bulger and Flemmi. Weeks's book, Brutal: The Untold Story of My Life Inside Whitey Bulger's Irish Mob, gives us the most intimate, well-rounded portrait of the complicated criminal. In Weeks's account Bulger continually defies stereotype.

"Sure he was all the things people said he was: a killer, fierce, forceful, dangerous," Weeks writes. "But he was also fair, respect­ful to people and their opinions, treating most of them courteously. If someone was right or had a valid point or opinion, he gave them credit tor their attitude. Some­times he did things I didn't understand, but I knew he had his reasons, and I would never question them."

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Weeks is in his early 50s, with dark curly hair and electric-blue eyes. He has the charm and easy repartee of an Irish pub­lican. He did close to six years in federal custody after pleading guilty to federal racketeering and admitting to participating in five murders. He cooperated with the government, leading investigators around Boston to shallow graves where the remains of eight of Bulger's victims were unearthed. As he finishes his pizza and tucks a pinch of Skoal beneath his bottom lip ("a habit I picked up in the can," he says), it's hard to imagine his assisting Bulger and Flemmi in their bloody reign of terror. Yet Weeks speaks almost casually about the killings. Bulger would take a nap after murdering someone, Weeks recalls. He would lie down on the sofa and doze off while Flemmi sat on the corpse and pulled teeth with a pair of Channellock pliers so the bodies couldn't be identified using dental records.

(A Southie Irish gangster named Pat Nee relates a story about the killing of a crook named John McIntyre. Nee says he brought Mclntyre to his brother's home, where Bulger, Flemmi and Weeks were waiting. Net-left for an hour and returned to find Mclntyre lying face up on the dirt floor of the basement with bullet holes in his head. "Stevie had a pair of pliers and was on his knees pulling out Mclntyre's teeth; you could hear the teeth separating from the jawbone.")

Bulger was a living paradox of loyalty and treachery. One of my favorite Bulger stories, which Weeks details well, concerns a vow Bulger made to a fellow prisoner in Alcatraz, a Choctaw Indian. Clarence Carnes, known as the Choctaw Kid. When Carnes died and was buried in a pauper's grave near the federal prison hospital in Springfield, Missouri. Bulger paid $10,000 to have the remains exhumed and removed to Oklahoma, where Carnes was given a proper ceremonial burial in con­secrated Choctaw soil so his spirit could ascend to the happy hunting ground. Bulger attended the ceremony. Hand­ing out $100 bills to Choctaw Clarence's relatives, he introduced himself as "Jim, a friend from Boston. "

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"People say Carnes was Whitey's gay lover in the joint and he died of AIDS," Weeks says, "That's bullshit. He was an alcoholic. That was what got him in trouble in the first place. He died from cirrhosis of the liver."

When I tell Weeks of my run-in with Caruana and of Bulger's intervention, he smiles. "You know what happened there? Jimmy and Stevie started shaking down Caruana."

Weeks believes they will never find Bulger. "Jimmy's too smart. He's way ahead of the game." He says Bulger had been planning to go on the lam for years. He rented safe-deposit boxes and stashed money all over the world. He says he thinks that since 9/11 Bulger has avoided the United States due to the additional security. But like nearly every­one I spoke to, Weeks says Bulger could be anywhere. He was so good at disguising himself, at times even his own family mem­bers wouldn't recognize him as he cruised around Southie, hunting his prey.

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"Could he be in Southie?" I ask.

Weeks smiles. "Who knows?"

Weeks met with Bulger five times after he became a fugitive.

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"How do you feel about Whitey now?"

"Betrayed," Weeks says. "We were killing guys because they were informants, and all the time Jimmy and Stevie were informants."

And John Connolly?

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"Connolly will end up doing more time than any of us." he says. "He's a scapegoat."

As we are about to leave the deli, Weeks stops at the front door. "You go out first," he says, an Irish twinkle in his eye.


The feds believe one man knows more about Bulger than he is letting on: Con­nolly. When Connolly was convicted of obstruction of justice, in 2002, the verdict was controversial. Witnesses testified that he had tipped of Whitey that the law was going to sweep in and that Connolly had pocketed thousands of dollars from Whitey and his crew over the years. A closer look reveals, however, that three of the four major witnesses who testified against Con­nolly were admitted murderers, all seeking ways to lessen their sentences. A fourth key witness was Connolly's own boss, John Mor­ris, who admitted to accepting bribes from Bulger. Morris was offered immunity to tes­tify. He has never served a day in prison.

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In the Florida case this past fall, prosecu­tors convinced a jury that, in 1982, Connolly tipped off Whitey that a gambling executive was about to cooperate with the Feds in a murder case that was going to land Bulger in prison for life. Subsequent to the alleged tip-off the gambling executive was found in the trunk of his Cadillac with bullets in his head. The main witness who testified against Connolly in that trial? Bulger associate and hit man John Martorano, who did the kill­ing himself. Martorano is hardly a stand-up guy. He admitted to 20 killings in 1995 and served 12 years, far less time than Connolly is likely to do. While Connolly faces life in prison, Martorano is a free man.

Many of Connolly's fellow agents maintain his innocence to this day. They believe that the Top-Echelon Informant Program, being as secret as it was, would make the cozy rela­tionship between Bulger and Connolly seem very suspicious to juries. Some believe that the witnesses who testified against the for­mer FBI agent had motive to lie.

Guy Berado, a retired FBI supervisor, worked with Connolly. "Agents were expected to develop informants," Berado says during a meeting in New Jersey. "That was what we did, dealing with murderers and thieves. Some guys had it; other guys could work for years and not open up one source." Connolly, Berado says, "broke the record for develop­ing made or 'proposed' guys as informants."

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Connolly had an uncanny ability to flip high-level Mob guys. His life was peopled with powerful crooks and killers. It was not rare for Connolly and his most high-profile informant, Bulger, to have dinner together. The closer they were, the safer they were. The information Connolly got from his TEs, including Bulger, led to some of the most vis­ible busts in Mob history. "It is recorded in FBI files that John was the key to the demise of the Patriarca crime family." Berado says. "Information John got from his TEs led to the arrest of 40 made Mafia members during the 1980s." Berado holds up a hand and signals me to take note. "And this is very important," he continues. "The October 29, 1989 record­ing: This was the first time the Bureau had ever recorded an actual Mafia induction cer­emony, and John gets the credit for that."

Using day-to-day updates from Bulger, his partner Flemmi and another informant, FBI agents planted a bug in the basement of a suburban home in Medford, Massachu­setts. The wire was used to obtain one of the most damning Mafia tapes of all time. Four new members were made in a traditional Mafia induction ceremony. One of the pro­posed men, Vinny Federico, was in prison at the lime, doing a bid for attempted mur­der. On his application for a weekend fur­lough, Federico described the necessity for the leave as "family business."

When it was over, the FBI had the entire secret ritual, in Sicilian and English, on tape. For visuals they snapped surveillance photographs of the departing mafiosi. FBI director William Sessions traveled to Bos­ton to personally congratulate the agents responsible for the induction-ceremony bugging, singling out Connolly for his han­dling of informants and calling the induc­tion tape the most important weapon in the FBI's war on organized crime.

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Berado closes his eyes and shakes his head in bewilderment. "John Connolly was a loyal, hardworking agent," he tells me. "He worked his ass off for the Bureau. He's a hero. What they are doing to him is heinous."

Joe Pistone couldn't agree more. Pistone, a.k.a. Donnie Brasco, knows a thing or two about the Bureau and the underworld. As an agent for nearly three decades, Pistone worked undercover for six years, infiltrat­ing the New York Bonanno crime family in Operation Sun-Apple. His book, Donnie Brasco: My Undercover Life in the Mafia, was made into a movie starring Johnny Depp as Pistone and Al Pacino as Pistone's Mafia mentor, Benjamin "Lefty" Ruggiero.

I meet Pistone in front of a nondescript strip-mall deli in New Jersey. Now in his late 60s Pistone looks relaxed, serious—nothing fake or soft about this man. Pistone tells me he has been a close friend of Connolly's for more than 30 years; they remained in con­tact even while Pistone was living in the underworld as Donnie Brasco. "John was one of the few people I was in touch with while I was undercover," he says. "That's how much I trust him." Pistone attributes Connolly's success at cultivating and han­dling informants to his ability to relate to the gangsters the Bureau was targeting.

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It was understood, Pistone says, that agents and informants would have to form relationships and that informants would continue committing crimes. "If you have a top-echelon informant like Bulger, you know you are dealing with a killer," Pistone says. "But you let them know that they will not be protected from prosecution for capital crimes. Anything but murder. You know, for me and John, it was all about doing a job we were sworn to do."

As far as the obstruction-of-justice count Connolly was convicted of in Boston in 2002—the charge that he tipped Bulger off to imminent indictment so Bulger could abscond—Pistone does not believe it. "John had been out of the Bureau for, what, four years when Bulger went on the lam? No one is calling a retired agent to tell him they have an indictment against one of his former infor­mants," Pistone says. " It ain't happening. They keep that information close to the vest."

"Do you think Whitey is still alive?" I ask.

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He nods solemnly. "We would know if he was dead. Somebody would take credit."

"Where do you think he is?"

"Probably in Europe—England or Ire­land—moving around. At his age, as long as he has good ID and money and does not contact any of his old associates, he can stay-on the lam indefinitely. It's going to be diffi­cult to catch him. It's not like the guy stands out. But I do believe they are looking."

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Pistone goes on to say he met Bulger once. He had dinner with him, Flemmi, Connolly and another Boston FBI agent. "It's on record," he adds. "I got a real sense of his intelligence," Pistone recalls of his meeting with Bulger. "The guy was quiet, a thinker. He didn't need John to tell him what was going on."

"Look, you know this," Pistone continues about his old friend Connolly, who at the time of our interview is sitting in the Hole in Florida, awaiting trial. "Since when do they keep a federal prisoner locked up in a county jail for years waiting to go on trial? They take you out on a writ, indict you, then bring you back to the prison where you're serving your time. Not John." He pauses. "Something's not right here. They're trying to squeeze him."


One of the more intriguing scenarios swirling in Bulger's wake is the super-rat theory. It stems from a botched 1984 arms-smuggling venture in which some Boston crooks and IRA operatives tried to move seven tons of weapons to Ireland aboard a 77-foot fishing trawler called the Valhalla. Bulger was involved in the plot; he hooked up gangster Pat Nee with a pot smuggler named Joe Murray, who provided the boat and financed the ill-fated escapade.

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The Valhalla made it across the Atlantic and unloaded the guns oil the coast of Ireland. Soon after the off-load was complete the Irish navy swept in and busted the IRA soldiers. They had clearly been tipped off. The Valhalla was allowed to leave the scene and return to the United Stales. An indictment came down on April 15, 1986—18 months after the incident. Two principal partners, Nee and Mur­ray, were sentenced to prison. Bulger didn't go on the lam until nine years after I he Val­halla incident, yet he is the only major figure involved who was never indicted.

Questions linger like the smell of bilge-water and diesel fuel waiting from the hold of the Valhalla Who lipped off Irish intelligence? Why was Bulger never charged?

The super-rat theory holds that Bulger dropped a dime on his own operation. He snitched on himself. By doing so, some believe, Bulger became an informant for agencies higher than even Connolly's

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FBI—the CIA, top-level officials in the Jus­tice Department and British intelligence who continue to protect him to this day. Without Connolly ever knowing it, Bulger began to operate not only at the elite level of cops and crooks but possibly where the two meet and become one: in the rarefied world of spooks, of super rats. One current law-enforcement official who asked not to be identified told me Bulger is still pro­viding valuable intelligence at the highest levels of international crime.

Lending credence to this theory is the tact that the last confirmed Bulger sighting was near London's Piccadilly Circus in 2002. A British man who had met Bulger years ear­lier working out in a gym and knew him well says he bumped into Bulger in the street.

"Hey, mate, how have you been?" the man said.

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Bulger looked startled. "You must have the wrong person," he replied and disap­peared into the crowd.

Following this sighting, the story of Bulger's flight from justice was beamed into living rooms across England on Crimewatch UK, the British version of America's Most Wanted. A safe-deposit box in Bulger's name, containing $50,000 in cash, was located in a London bank. Calls reporting suspected Bulger sightings poured in. Yet when a team of American investigators arrived in England and asked for assistance from New Scotland Yard to follow up on the leads, the Brits ini­tially helped but then quickly begged off, claiming they were too busy tracking Mus­lim terrorists to be concerned with some aging Irish American gangster.

Weeks says Bulger traveled extensively in Europe and South America during the years after the Valhalla incident and before he became a fugitive, either on his own or with Flemmi. Weeks also says he would not dismiss the theory that they were doing "work" for the government, and he defi­nitely believes the murderous duo did hits for other organizations. 'They were very good at what they did." he adds.

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A necessary element of the super-rat theory is the existence of a scapegoat, a fall guy—in the words of JFK assassin Lee Harvey Oswald, "a patsy." As in, "I'm just a patsy." The theory posits that spooks oper­ate with impunity on both sides of the law, doing "black ops," dirty work for elements within the government—like the former CIA men arrested breaking into the Demo­cratic National Committee headquarters in the Watergate affair, or like Oliver North, who ran a clandestine arms operation out of the basement of the White House in the Iran-Contra scandal. Black ops require the existence of fall guys to act as receptacles for the public's outrage and to provide a sense of closure. Oswald. Sirhan Sirhan, James Earl Ray, C. Cordon I.iddy, even Richard Nixon. Add Connolly's name to the list.

Whether you believe, as juries did, that Connolly came under the spell of Whitey and became one of his criminal pawns, or that in fact the crooks who surrounded Whitey con­spired to land Connolly in the position he is in today, no one could argue that Connolly is not a fall guy. Never in a court of law was Connolly ever accused of lifting a finger against another man or ordering any hits. Yet he will serve more time than all but one of the men who testified against him, the majority of them admitted mass murderers.

During a recent stay in Boston I received a thick packet of documents from a group calling itself the Friends of John Connolly. One document contains excerpts from what is known as a DEA-6, a debriefing report of a government's cooperating witness, in this case Bulger's partner, Flemmi, who began talking with government prosecu­tors alter Bulger lied. The Flemmi report makes a compelling case that Connolly was framed with perjured testimony pro­vided by Frank "Cadillac" Salemme, a mobster who hated Connolly because Connolly had put him behind bars. The Flemmi DEA-6 contradicts all the charges brought against Connolly in his 2002 case.

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This highly excul­patory evidence was not provided to Con­nolly's defense law­yers. Instead it was placed under seal.

Another docu­ment included in the sheaf of papers is FBI Report FD-302, known as the Vella Report, which was also concealed from Con­nolly's defense lawyers at the time of his 2002 trial. This report con­tains statements from Roger Vella, who was locked up with Frank Salemme in a witness-protection unit of a federal prison at the time Salemme testi­fied against Connolly. Vella told FBI agents Salemme bragged about his perjury, say­ing he could "get a thousand years" for the lies he told on the witness stand. It had been "his chance to get even with Con­nolly and make the FBI look like 'the shit they are.'" Signifi­cantly, Salemme told Vella he believed his cooperation against Connolly "negated the need" for the government to find Bulger.

Bulger may be in the wind, but federal prosecutors had their whipping boy. And the spooks had their patsy.


Connolly did have a way out. Before his 2002 trial he was offered a deal: Testify against other agents in the Boston Bureau in corruption cases involving TEs, and he could walk. He turned it down.

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"Why are they doing this to you?" I ask him.

Our time is nearly up. The lanky guard with the jangling keys has reappeared.

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"I want to make it clear," Connolly answers. "The FBI is not doing this to me."

"Then who is?"

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"Ambitious Justice Department prosecu­tors, John Durham and Fred Wyshak. They got themselves out on a limb by creating the false perception that there was all this sup­posed corruption in the Boston FBI office, when nothing could be further from the truth. They took the uncorroborated word of career criminals, men who murdered 20 and 19 victims, respectively, and used that to go after distinguished FBI agents who dedicated their lives to honorable public service."

I press him. "But why specifically did they target you?"

"Look. I know a little about your history, which is why I agreed to talk to you," Con­nolly says as he shoves papers back into his portfolio. "You know how it works. I was offered a deal: Testify against other agents and Billy Bulger, and all this will go away. Billy Bulger knew nothing about my rela­tionship with Jim. And the only agent in Boston guilty of wrongdoing, to my knowl­edge, was my former supervisor, John Morris, whom these prosecutors adopted as their witness. They needed somebody to validate the lies their serial-killing witnesses told, who were trying to save themselves from a lethal injection or life in prison."

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Connolly stands, ready to return to his cell.

"I refused the deal." he tells me. "I'd pre­fer life in solitary confinement over the dis­honor of testifying against innocent men."


And where is Whitey in all this? If they have any inkling, the Bulger clan is steadfastly mum. One brother, Jackie, did six months for lying to investiga­tors, saying he hadn't had contact with Whitey. Billy took the Fifth when ques­tioned if he had communicated with his sibling. "The Fifth Amendment's basic function is to protect innocent men who might be ensnared by ambiguous cir­cumstances," he said. "I find myself in such circumstances." As a result he was forced to resign as president of the Uni­versity of Massachusetts.

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Fourteen years after Bulger's disap­pearance the Bulger Fugitive Task Force remains undeterred—and luckless. In the past year alone agents went to Mex­ico, England, Italy and Spain, hunting Bulger. From a secret location in Bos­ton—conference-room walls papered with pictures of Bulger, Catherine Greig, relatives and friends, maps of the world bristling with push­pins marking pos­sible sightings—the task force investi­gated more than 100 look-alikes and another 300 leads last year.

On one point in the Bulger biogra­phy there is uni­versal agreement: He is a criminal genius, a man who understands how to play both sides of the law. He is a long-range thinker, a man with a vision. A bid in Atlanta and Alcatraz with ample doses of pure LSD will do that to a man. Lying in his cell one night, ripped to the tits on acid, perhaps he had a breakthrough, a revelation: In the world of cops and crooks, he realized, there is no honor, only survival. He saw himself lying on a beach with his blonde babe and his stash of cash, living the convict's dream.

Now, as he watches himself being pur­sued on America's Most Wanted. Bulger snickers in his soup. "Catch me if you can," he taunts from parts unknown. He's a Houdini of whodunit, a Scarlet Pimpernel of crime. The feds seek him here; they seek him there; they seek him everywhere. But Bulger remains in motion. No fixed address. He's a lamster like Bin Laden. His home is travel itself. Wherever he is going, that's where he is. And about the time they figure out where he is, he's already somewhere else.

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It beats the hell out of being in a jail cell. Just ask John Connolly.


This article originally appeared in the January 2009 issue of Playboy.