The Secret Life of Whitey Bulger

By Richard Stratton

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The Secret Life of Whitey Bulger :

On a cool Wednesday evening, June 22, 2011, FBI agents with the Violent Crimes Task Force gathered at the Bureau’s Los Angeles headquarters on Wilshire Boulevard. They were joined by deputy U.S. marshals and heavily armed members of the LAPD SWAT team. The agents and cops were wired, tense with anticipation, for they were hoping to take down the FBI’s most wanted man, a criminal who had evaded capture for more than 16 years despite one of the largest worldwide manhunts in history.

That man, these agents believed, was living with his mistress in an apartment complex in Santa Monica just five miles from where the task force had assembled. James “Whitey” Bulger, criminal mastermind and Top Echelon FBI informant, was wanted for racketeering, extortion and drug dealing, as well as for his alleged participation in at least 19 murders. The agents believed Bulger, now 83 years old, was living under the alias Charles Gasko at 1012 Third Street, two blocks from the beach in Santa Monica, always paying his $1,145 rent on time, always in cash. The painstaking planning centered on how to capture Bulger now that the FBI was convinced it finally had him in its sights. Bulger was considered to be armed and extremely dangerous. An ex-con who had served time in California’s infamous Alcatraz penitentiary, he had sworn he would never go back to prison.

The Bureau did not want to screw it up this time. For years the agency had been humiliated time after time in locations around the world—from England to Australia, Italy to Ireland—as tips and reported sightings had failed to produce an arrest. Bulger was a phantom. There was rampant speculation that he was in fact the FBI’s least wanted fugitive, that the Bureau was merely making a show of trying to find him for fear of the consequences of his arrest—of what his secrets would reveal not just about the underworld but about the U.S. justice system itself.

At last the bust was about to go down. Sharpshooters had the tree-shaded building surrounded. Fearing a shootout, they decided not to break down the door and go in with guns blazing. Instead they concocted a ruse to lure the gangster from his lair. Agents contacted the building manager and instructed him to call the apartment. When the man they believed was Bulger answered, identifying himself as Mr. Gasko, the building manager told him a storage locker he was using in the basement of the building had been broken into and asked him to come down to make a claim.

The balding, white-haired man shuffled from the apartment and took the elevator to the basement. He wasn’t noticeably surprised or even upset when he walked into the trap and found a small army of federal agents with guns pointed at his head.

“James Bulger!” an agent yelled. “You’re under arrest! Put your hands on your head. Drop to your knees. Lie facedown. Hands behind your back.”

Agents swarmed around him like paparazzi on Brad Pitt. There was that familiar click and grip of the cuffs around his wrists.

“Yes,” he admitted, “I am James Bulger. You got me.”

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Whitey Bulger smiled. At last he could stop running.

The agents took him back upstairs to the apartment, where his 60-year-old companion, Catherine Greig, awaited. There the investigators uncovered almost a million dollars in cash and a huge arsenal of weapons.

Bulger looked at his longtime live-in girlfriend, on the run with him for all these years. “Honey,” he said, “it’s time to go home.”

Phones rang in the offices of cops, agents, politicians, lawyers and prosecutors and in the homes and hideouts of crooks big and small all over the globe. Bulger’s flight had ended.

For Whitey Bulger was not just some run-of-the-mill bad guy. He was a mythic figure, a folk hero and ruthless murderer, the great criminal mastermind of our time. Loosely portrayed on the silver screen by Jack Nicholson in the Martin Scorsese film The Departed, Bulger ranks on a level with Gotti, Capone and Escobar, and even higher in his hometown of Boston. While executing his alleged 19 hits—strangling and stabbing his victims, dismembering their bodies and yanking out their teeth with pliers to thwart identification—Bulger and his partner, Stephen “the Rifleman” Flemmi, ruled the New England rackets for decades. All the while, it had long since been revealed, they were what is known as Top Echelon FBI criminal informants, or TEs. They were FBI assets. While Bulger and Flemmi ran New England’s underworld, they were protected and allowed to remain active by high-ranking officials within the Department of Justice.

The FBI claims that after a 16-year manhunt it finally got wind of Bulger’s whereabouts after disseminating a 30-second public-service ad focused on his female companion, the elegant Greig, a former dental hygienist who was known to frequent beauty and nail salons. Aired primarily during women’s TV shows such as Ellen, The View and Dr. Oz, the ad produced more than 200 calls. According to inside sources, a young deputy U.S. marshal zeroed in on the lead that ultimately led agents to Bulger—a mere two days after the ads started to air.

The tip supposedly came from Miss Iceland 1974, Anna Björnsdóttir, still stunning at 58, a former B-movie star living in southern California. Björnsdóttir recognized Greig, whom she had befriended over a stray cat the ladies encountered in the streets of Santa Monica. That pussy cost Bulger his freedom and earned Björnsdóttir a $2 million reward.

But in the highest realms of the Department of Justice, and for students of the Bulger saga everywhere, the capture is not the end of the story but a new beginning. The gangster is a man of many secrets. He holds information that if exposed would send shock waves through the hallowed halls of the Department of Justice. Here is Bulger’s opportunity to end all the lies and tell the world what he knows.

There is one man who stands to gain the most by having the truth emerge. That man is former special agent John Connolly, Bulger’s FBI handler. A long time ago Connolly was a highly decorated agent. Now he has been in prison almost as long as Bulger was on the run. Connolly was headed to the yard for a workout at a federal prison in North Carolina when he heard about Bulger’s takedown. All through his workout, the news of the arrest played in Connolly’s mind. When he finished his exercises and returned to the housing unit for the evening count, Bulger’s capture was all over the airwaves.

Connolly’s side of perhaps the biggest law enforcement scandal of our time has never been fully told. Until now. In a series of telephone interviews from prison, Connolly spoke about the potentially game-changing arrest of Jim Bulger, his longtime Top Echelon criminal informant.

“Was I surprised to hear they caught Jim?” Connolly says. “Yes…but then again no. Yes because Jim had been a fugitive for so long, and as an FBI agent I realized the trail of someone that bright and that disciplined is usually ice-cold after 16 years. I knew Jim Bulger wasn’t going to be making the usual mistakes that result in fugitives being apprehended.

“Later,” Connolly remembered, “when I caught up with the news on TV, it hit me. This thing is going to get blown wide open. The potential evidentiary value of Whitey Bulger finally exposing the truth of his relationship with the Department of Justice—and what was done to me to cover that up—cannot be overestimated. That could finally set me free.”

South Boston is a neighborhood in the true sense of the word—an Irish American enclave physically and psychologically separate from the rest of the city. It even has its own song: “Southie Is My Hometown.” In the Old Harbor housing project, three Irish American youths were born before World War II to a shared destiny: One would reach the lofty heights of the famously clannish Massachusetts political machine, one would rise to the highest ranks of national law enforcement, while the third would seize the bloody crown of the New England underworld. All three would end up embroiled in a scandal that reached the highest levels of the American justice system.

Whitey Bulger got his elementary education in crime as a teenager running with a Southie street gang known as the Shamrocks. He became a journeyman criminal in league with a crew of bank robbers while still in his 20s and was named to the FBI’s most wanted list. Bulger did his first major prison stretch at the federal penitentiary in Atlanta. While there, in the 1950s, he volunteered to ingest massive doses of LSD as part of the CIA’s MK-Ultra program. Becoming a human guinea pig earned him a reduction in his sentence. He was transferred to Alcatraz, the Harvard of penitentiaries, where he received the equivalent of a doctorate in criminality. An avid reader and a long-range thinker, Bulger studied military history and warfare tactics while locked up, absorbing such classics as Sun Tzu’s The Art of War and Machiavelli’s The Prince. He emerged from the penitentiary a master criminal on acid and was soon in the thick of the mob wars raging in Boston in the 1960s and 1970s, working his way up until he was running the notorious Winter Hill gang out of Southie.

Whitey’s younger brother Billy took the opposite road. He became a “triple eagle” graduate of Boston College High School, Boston College and Boston College Law School before entering local politics. After 17 years in the state senate, Billy was named president of the University of Massachusetts. Later, after his gangster brother absconded from the law in 1995, Billy was hounded out of public life by then Massachusetts governor Mitt Romney for refusing to testify before a grand jury investigating Whitey.

Like most of the kids in the neighborhood, young Johnny Connolly was in awe of Whitey. He heard the stories of Whitey having an affair with a stripper from the Old Howard burlesque hall and running off with a traveling circus while most kids were still in school. But Connolly was closer in age to Billy Bulger, and they became friends. Connolly chose to follow Billy’s lead. He got a good education before embarking on a career in law enforcement with the FBI.

As a young street agent in Manhattan, Connolly was walking along Third Avenue on a cold December day in 1972 when he recognized fugitive Boston mafioso Francis “Cadillac Frank” Salemme walking toward him. Salemme was a suspect in numerous gangland hits and had been indicted for planting a car bomb that blew one of the legs off a Boston attorney. After a foot chase that ended when Connolly tackled Salemme at the corner of 81st Street, Connolly took the fugitive into custody virtually single-handedly. With the Salemme arrest, Connolly got his wish: He was transferred back to his hometown to work the underbelly of Boston, where both the Irish and Italian mobs were thriving even as they warred for dominance.

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.

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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.

The FBI was forced to admit Bulger and Flemmi had been informants. But the prosecutors and Department of Justice higher-ups were loath to acknowledge that as TEs they had been given immunity from prosecution in exchange for their intelligence. Connolly refused to play along, and as a result he became the DOJ’s whipping boy, its scapegoat.

By October 2000 Connolly had been charged with nine counts of criminal action, including racketeering, obstruction of justice and making false statements to law enforcement officials. Essentially the government prosecutors attempted to prove that instead of merely handling his Winter Hill informants, Connolly had joined Bulger as an active member of his gang. The trial had the city of Boston riveted. Connolly was found guilty of racketeering, obstruction of justice and making false statements. Bulger was gone, and the feds needed to save face. Using testimony from a Winter Hill gang insider (testimony that was later discounted by another witness), a jury found Connolly guilty of tipping off Bulger to the impending indictments so he could flee before the law came for him. The judge sentenced Connolly to 10 years in federal prison.

Seven years later, Connolly was wrapping up his federal bid when he was charged in Miami with conspiring with Bulger and others to murder a shady Boston businessman named John Callahan. The former president of World Jai Alai, Callahan was involved in a scam with Bulger—until he was found riddled with bullet holes at the Miami airport in the trunk of his Cadillac. The charge claimed that Connolly had tipped Bulger off that Callahan was going to drop a dime on him for the murder of World Jai Alai owner Roger Wheeler. Callahan’s body had been found with one dime facing up on his chest. Connolly was transferred from the federal prison in Butner, North Carolina to the Turner Guilford Knight Correctional Center in Dade County, Florida. He was held in the hole on 24-hour-a-day lockdown.

At the Miami trial, prosecutors trotted out a rogues’ gallery of hit men and snitches to testify; it was in all of their best interest to take Connolly down. Connolly’s former supervisor John Morris again took the stand and wept through his testimony. Although he admitted to accepting thousands in cash and a case of fine wine from Bulger (Bulger called him Vino for his fancy palate), Morris testified against his underling Connolly and walked without ever spending a minute behind bars. Hit man turned government witness John Martorano—who admitted to committing the murder and placing the dime on the victim’s chest after shoving the body into the trunk of the Cadillac—testified against Connolly. Today Martorano, known as the Basin Street Butcher and with more than 20 confirmed notches in his belt, is a free man often seen dining in fine Boston restaurants. Another admitted murderer who testified against Connolly in exchange for a lesser prison sentence is Bulger’s partner Flemmi.

Connolly was convicted of second-degree homicide with a firearm and sentenced to 40 years in prison—a virtual life sentence. His Miami lawyers belatedly pointed out that in cases involving the crime for which he was convicted—second-degree murder with a firearm—Florida statute requires that it be proved beyond a reasonable doubt that the firearm used in the murder was in the personal possession of the defendant during the commission of the felony. That element of the crime was never proven; in fact it was never even alluded to in the state’s case. The only firearm in Connolly’s possession would have been his FBI-issued weapon, which was with him in Massachusetts, hundreds of miles from the scene of the crime.

The trial judge agreed with Connolly’s attorneys that the jury’s verdict, and therefore Connolly’s conviction, was flawed. But, he pointed out, the lawyers had filed their motion for arrest of judgment several days beyond the 10-day period allowed by law. Because the motion had not been filed in a timely manner, the judge ruled that the conviction and 40-year sentence would stand. And the appellate court in Miami denied the appeal without issuing an opinion.

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As Connolly watched his life slip away in a Florida prison, FBI agents maintained their command center in Boston and spent millions on one of the most elaborate and expensive criminal manhunts ever mounted. All the while, Whitey Bulger and his lady, Catherine Greig, were living quietly in Santa Monica, hiding in plain sight.

On the eve of the Bulger trial, it seemed a worthy endeavor to travel to Boston to interview some of the people who had been closest to him back in the day when he was assuming control of the underworld and conniving with FBI agents.

Theresa Stanley was in a relationship with Bulger for 30 years. She was on a road trip around the country with Bulger in January 1995 when they heard the news on the car radio that Flemmi had been arrested. In her early 70s, Stanley sat for an interview over lunch at Legal Sea Foods. A delicate woman still mourning the drug-overdose death of her son—a son Bulger had helped raise (“Jim was very strict,” she remembered of Bulger’s parenting skills)—Stanley was also still suffering from Bulger’s betrayal: All the while he was with her, he had two other mistresses, Catherine Greig and longtime girlfriend Lindsey Cyr, with whom he had a child, a boy named Douglas.

“It’s hard to understand,” she said over a bowl of lobster bisque. “I don’t know how a man can live so many different lives and keep up so many lies. It must not be easy.”

Reminded that Bulger, given his dual role as informer and mobster, was adept at living multiple realities, Stanley gained little solace. She had resisted telling her story because the whole thing brought up too many unhappy memories. She agreed to meet only after her son-in-law Chris “Knuckles” Nilan, a former enforcer for the Montreal Canadiens hockey team and a Bulger confidant, had put in a good word.

Stanley confirmed that Bulger had planned for his flight long before he learned of the indictments and Flemmi’s arrest. “He was traveling under his own name while we were together,” she recalled. “But he was aware something was going on back in Boston.”

Once they heard about Flemmi and the warrant for Bulger’s arrest, Stanley said, Bulger immediately stopped using his real name and assumed the identity of Thomas F. Baxter, who had died in January 1979. In 1990 Bulger had obtained a driver’s license in Baxter’s name and had renewed the license again in 1994, a year before he went on the lam.

“Connolly never tipped Jim,” Stanley said. “We weren’t even in Boston at the time. Jim heard the news on the car radio. It’s not right what was done to Connolly. Jim should clear Connolly. He should do that. He should do one good thing before he dies.” Stanley succumbed to lung cancer and died just months after our interview.

It is well established that Bulger had already planned his flight and left town by the time the Boston indictments were unsealed. He had phony IDs and cash at the ready. Connolly had retired from the FBI four years before the indictments. As another Connolly supporter, former FBI agent Joe Pistone, known as Donnie Brasco while working undercover for the FBI, explains, “No one is calling a retired agent to tell him they have an indictment against one of his former informants. It ain’t happening. They keep that information close to the vest.”

Pistone knew Connolly when they were both on the job. “All John Connolly did was his job, what he was hired and sworn to do,” Pistone says.

Hockey player Nilan believes that in addition to clearing Connolly, Bulger wants to set the record straight on several of the killings attributed to him. “Jimmy said to me, ‘The last guy to come in always gets blamed for everything,’” Nilan says. In particular, Nilan and others close to Bulger believe that Flemmi’s testimony against Connolly was self-serving in the extreme, that he lied about several murders Bulger supposedly committed, that he heaped the blame for killing two of Flemmi’s ex-girlfriends on Bulger and that government prosecutors knew Flemmi lied and therefore committed perjury.

“Jimmy’s very smart,” Nilan says. “I’m sure he’s still got a few cards he can play. Believe me, they don’t want to hear what he has to say.”

Lindsey Cyr—mother of Bulger’s only child, Douglas, who died of complications from Reye’s syndrome when he was six years old—has stories of Bulger few except those closest to him ever knew. Cyr met Bulger when she was 19 and had a second job as a waitress in a restaurant Bulger frequented while he was working for a construction company soon after his release from prison.

“Jimmy was very quiet and well-behaved,” Cyr told me in a television interview, “a gentleman, at least with me. He had beautiful manners and was so handsome—the blond hair and those blue eyes. You couldn’t help but notice him.”

Cyr’s boyfriend got rough with her one day in the restaurant while Bulger was there having breakfast. “Jimmy took him outside, talked to him for a second and then folded him up with four straight shots,” said Cyr, remembering how Bulger became more than just another customer. Bulger returned to his seat and told her, “That won’t happen again. If it does, I will be forced to become unpleasant.”

She started dating the older man. He took her to a cookout at Billy Bulger’s South Boston home, where she met Billy’s wife and their many kids, as well as the brothers’ mother, Jean Bulger, to whom Whitey was devoted.

“He was still living at home, taking care of his mother,” Cyr said. “I guess that’s something Irish men do.”

Other dates were not so relaxed. Twice while out with Bulger, Cyr said, they were caught in gun battles with shooters trying to take him out. “He explained he was reorganizing Southie,” she recalled. There was a mob war raging in Boston at the time, and Bulger had landed himself in the middle of it.

Cyr remembers him as an “incredible,” well-endowed lover. “First time I saw him naked, I was shocked,” she said. “I told him, ‘No way you’re going to put that in me!’ But he was very gentle. Sex was a major item for Jimmy. I mean, it was like breathing. And he had to have it when he wanted, and that meant any time I was in the vicinity.”

Inevitably she became pregnant and gave birth to a baby boy. Cyr remembers Bulger as a doting father who was crazy about Douglas, his look-alike towheaded little boy. But Bulger was concerned about the exposure having a wife and child could mean to his enemies during his “reorganizing” of the underworld. He chose not to give the child or Cyr his name and kept them as much as he could out of harm’s way. She says Bulger changed after the boy’s death. “Jimmy became very cold. He said to me, ‘I can’t hurt like this. I don’t think I can go through life just as we always have with the exception of no Douglas.’ That was the one time he mentioned his name after Douglas died.”

Eventually they drifted apart. Cyr remembers the last time she heard from Whitey was in January 1995. He called at three in the morning and told her, “There’s trouble. I’m going away for a while. But everything’s under control. I’ve got insurance, and it’s gold-plated.”

“I don’t know what kind of insurance he’s got,” Cyr said, “but I honestly believe that several of the people who are walking around should be in jail, and certainly not the FBI agent. John Connolly, they threw him to the wolves.”

Bulger is now being held in solitary confinement in the maximum-security unit of a prison in Plymouth, Massachusetts. He’s made more than a dozen appearances in federal court in Boston, shuttled in and out by helicopter or in a caravan of armored black Suburbans. He smiles and nods to the media entourage that flocks to his every appearance. He waves and greets his loyal family members, in particular his brother Billy, who shows up at every hearing. His companion, Catherine Greig, was sentenced to eight years in prison after pleading guilty to harboring Bulger. She is serving her sentence in a low-security women’s penitentiary.

Bulger’s upcoming trial is the most anticipated public airing of the biggest law enforcement scandal of our time. Through his court-appointed attorney, J.W. Carney, Bulger declared that he intends to take the stand and name names, to tell of the higher-ups within the Department of Justice who authorized him as an informant and granted him immunity. He has insisted on only person-to-person communications with his lawyers, claiming that all his calls are monitored, even the protected attorney-client calls, and asserting his belief that all law enforcement is corrupt.

But the trial may never happen. Bulger turned 83 in September. He has a heart ailment. People held in custody with medical conditions tend to die. And already the feds are making moves to ensure that the full dimension of Bulger’s complex relationship with Connolly and his superiors in the Department of Justice is never brought to light.

Upon Bulger’s return to Boston to face the charges, prosecutors handling the case announced he would not be tried for any of the offenses in the original racketeering indictment that covered the period when he was a TE informant. A superseding indictment charges him only with the 19 murders he and Flemmi allegedly committed.

The judge imposed a tight gag order on Bulger’s attorney Carney, who has complained to the court that the order prevents him from talking to potential witnesses and is hampering his ability to prepare a defense. Given the machinations on both sides, it’s fair to assume that whatever comes out during the trial—if it takes place—will be a highly attenuated version of what really happened. The judge can simply rule that areas of Bulger’s evidence the government does not want made public are irrelevant, outside the purview of the current indictment or a threat to national security. End of story.

As Connolly says from prison, “It is my understanding that the many FBI agents who have been fighting to prove my innocence have been alerted by FBI officials in Washington, D.C. to evidence indicating Whitey Bulger has exonerated me and confirmed I was framed. I was also told he has implicated my admittedly corrupt former FBI supervisor, John Morris, in additional criminal wrongdoing, which proves Morris perjured himself both in his plea agreement and at both my trials. It is my further understanding these statements by Bulger have been documented in official FBI reports, but the reports are placed under seal by the Department of Justice and have not been provided to my attorneys. This comes as no surprise in light of all the other exculpatory evidence they concealed. Bulger has always kept his own counsel, for only he knows what he intends to do. Obviously it is my fervent hope that he will be allowed to take the stand and tell the truth and exonerate me.”


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