Southie Tales: How Whitey Bulger played both sides… and lost

The world of federal gangland informants is a shadowy one. Criminals play both sides of the fence in a twisted game of self indulgence, often pleasing both their law enforcement handlers and cohorts in the streets in a double-agent role. Then when the indictments come out, they disappear, reemerging to testify in court, before being whisked into the Witness Protection program. That is the theory, at least. In reality, the odds are stacked against anyone striving to uphold their reputation in the underworld while at the same time snitching on the men they are breaking bread and doing dirt with. Betraying the code of Omertà gets a criminal branded all types of labels – like a rat or a snitch or, as they call them in Boston, a tout.

Getting a jacket as a tout can ruin a gangster’s criminal career before it even begins. It’s a death knell to whatever street dreams they harbour. Touts are ostracised from the underworld hierarchy or even worse, killed for their betrayal.

“Touts are the lowest form of life,” a Boston mobster doing time in the Feds told Real Crime. He is in for a drugs and guns conspiracy and has asked that his real name be withheld as he goes through his appeal process. “No real man would sell out to avoid jail. You just do your time and get on with it. Anyway, its character building in the long run.”

Johnny Depp as Whitey Bulger in 2015's Black Mass
Johnny Depp as Whitey Bulger in 2015’s Black Mass

But some men make the decision to forego the unspoken death-before-dishonour vow that pervades criminal life. They choose to betray their comrades and work with the Feds, minimising their own exploits and putting cases on others to shift their culpability. Some are brazen enough to do it while still active in what they call the life or the game, playing both sides as they attempt to stay one move ahead.

Because in the criminal underworld, there’s only one rule: no snitching. When a gangster breaks the code, it can lead to death, but it can also lead to the destruction of his legacy in the chronicles of gangster lore. Gangsters are romanticised in our culture but informants are despised.

That didn’t stop Whitey Bulger, the Irish-American mob boss who ruled the Irish enclaves of Boston for more than two decades. He’s been immortalised in print and in film, but to those in his hometown, he is nothing more than a rat.

“Whitey Bulger had a long run and was king of Boston’s criminal underworld for a long time,” the Boston mobster said. “But he was leading a secret life. He was having his cake and eating it too. Making money, killing people and basically doing whatever the fuck he wanted to do. While at the same time working for the FBI and feeding them information on La Cosa Nostra.” Bulger was snitching on his competition to build up his own criminal empire. “And the thing was, no one ever suspected this of Whitey,” the Boston mobster said. “He was beyond reproach. The people in Boston were terrified of him, both criminals and citizens. Everyone knew not to cross Whitey Bulger. No one ever thought he was a snitch. He carried it so hard that he was seen as the ultimate gangster.”

Bulger's wanted poster
Bulger’s wanted poster

Bulger grew up in a housing project in South Boston and was busted early in his criminal career. He was sentenced to 20 years in federal prison. Bulger wasn’t anyone special back then, just another Irish hooligan brought into a life of crime by circumstances, but he would become the boss of bosses in Boston. After that case, everyone in the town figured he was the consummate stand-up guy, but he was ratting even then. FBI and prison records show Bulger began co-operating with law enforcement from the jump. “Bulger, after his apprehension, co-operated with this bureau,” states a July 1956 FBI report. Bulger informed the FBI who his accomplices were in the bank jobs they were suspected in.

However, from the start, Bulger didn’t want it on paper and he would never sign anything or testify in court. He felt this was his best defence against being labelled a tout. As long as there was no proof, then in his mind he didn’t do it. He was playing all sides against the middle. “He made these oral admissions but insisted that it not be put in writing,” said journalist Dick Lehr, author of Black Mass, the book that inspired the movie. No paperwork to muddy his trail.

“He rose to the top of a vicious underworld and managed to get away with it,” David Amoruso from organised-crime blog Gangsters Inc said. “That’s why people are so mesmerised by his story. A violent gangster who rose to the top by all means necessary, breaking all the rules of both the legitimate and underworld. Even manipulating the FBI. A true outlaw.”

After serving nine years of the 20 he was sentenced to, he got out, went home to Boston and set about making his name in the city’s rackets. He is alleged to have killed 40 people in his lifetime, starting with the bloody Boston gang wars of the 1960s, when many Southie gangsters were gunned down in the streets and seedy bars of the town, as rivals perpetuated a life-and-death struggle to be crowned king of Boston’s underworld. But Bulger wasn’t playing fair.

South Boston in 1965
South Boston in 1965

“He was a cheater,” the Boston mobster said. “He was vicious and smart and cunning and had all the factors he needed to thrive but he told it one step further. He wanted to hedge his bets, so to speak. He wanted to ensure he would always be on the winning side.”

As he was making inroads with the notorious Winter Hill Gang, he also formed a partnership with Steve ‘The Rifleman’ Flemmi, another rising criminal who had Mafia connections. But not all things were what they seemed.

Not even ten years into his re-emergence into the criminal ranks Bulger became an FBI informant again. With Flemmi by his side in the snitch game, he formed another important relationship with FBI agent John Connolly. The agent made Bulger his top-echelon informant in 1975. Due to Connolly’s protection, Bulger was able to make big power moves in the criminal underworld, unmolested by law enforcement.

“Whitey could do as he pleased because he was protected,” said the Boston mobster. “Everyone kind of knew what was up but no one could prove it, but people were definitely talking about it. Because, how else was everyone getting busted and Whitey never went to jail? He was like the Teflon Don. But the world knows now. It’s because he was a tout.”

FBI agent John Connolly and his immediate supervisor John Morris developed Bulger as their office’s prize informant; they sold him to the FBI as a top source of valuable information on the Italian Mafia, who the FBI had their sights on. But other law enforcement agencies, including the Massachusetts State Police, didn’t like the relationship Bulger had with the FBI. They were questioning the legitimacy of it even back then.

One-time Bulger ally Steve ‘The Rifleman’ Flemmi in
One-time Bulger ally Steve ‘The Rifleman’ Flemmi in

As the criminal stature of Whitey Bulger rose in the streets, so did his desire to protect his illegal rackets. He would protect them at all costs, resorting to killing, snitching, or whatever it was he had to do. On the streets he was known as a shrewd intimidator who played the thugs, drug dealers, street figures, local toughs and gangsters of Boston with equal aplomb. In the game of chess that Bulger was playing, no one could fathom what his next move would be. He kept everyone off balance and had the FBI in his back pocket.

The legitimacy of his co-operation with the government has been called into question by many quarters. Many think that Bulger, who was a master manipulator, never gave up anything to the government and in fact used them for information instead. The world wants to see everything in black and white, but sometimes that’s not always the case.

“Whitey is claiming that he paid the government cash and gifts in exchange for information and protection,” said Mark Silverman, a Boston mob associate and author of Rogue Mobster. “He claims that he gave them ‘shit and got gold in return.’ I’ve never been around any high-level gangsters who didn’t have contacts inside the circles of law enforcement. A rat testifies. He gets up on the stand and points the finger at the friends who cared for him his entire life.”

Despite all the criticisms of Bulger, he has never done that. But the questions about him being an informant remain. His 700-page FBI file and informant card gives proof that Bulger provided information on murders, drug deals, armed robberies and criminal fugitives, which led to several arrests. He also snitched on the Mafia and rival gangs, protecting only those in his inner enclave of the Winter Hill gang.

Bulger in police surveillance photos
Bulger in police surveillance photos

But at his latest trial, following his capture after 16 years on the FBI’s Most Wanted list, even an FBI agent questioned his legitimacy as a rat. “He said he would never testify,” said Robert Fitzpatrick, a former FBI agent who wrote the book Betrayal about his time in the FBI with John Connolly. “You can’t have the head of a gang as an informant, because then you’re validating the gang, you’re actually part of the management process, if you will.”

Fitzpatrick knew that Bulger was not a legitimate snitch because, as he said: “The worst thing for an Irish guy in Boston is to be a tout.” Whitey’s reputation was important to him and being labelled a snitch or tout was not something he could abide. He would kill to protect his secrets and he was so brutal to informants that no one would ever suspect. But usually it’s the person that goes the hardest against something that has the most to hide. The perfect ploy in Bulger’s case. But still there are doubters.

“I think he has an irresistible narrative,” said Joe Berlinger, whose documentary Whitey: The United States Of America Vs James J Bulger gives viewers an up-close look at Bulger’s life. “Here’s a guy who was on top of Boston’s criminal empire for 25 years, not even charged with so much as a traffic ticket. Whitey rises to the top of Boston’s underworld and he has a life of crime, extorting and killing his way to the top.”

Bulger’s MO is not in question. It’s a given fact that he lied, cheated and stole his way to the top of the criminal hierarchy. Nothing was out of bounds for him. “Whitey was the devil, pure and simple,” the Boston mobster told us. “He had no honour, he had no scruples or morals. No loyalty. Why he is held up as a man of honour in pop culture amazes me. He is no John Gotti.” But to his admirers, he is the classic Irish gangster. That’s why Berlinger made a film about him.

A later mugshot of Bulger
A later mugshot of Bulger

“What my movie tries to explore is some of the claims of the defence that Bulger, in fact, was not an informant – that there was evidence that demonstrates the relationship was much more corrupt,” Berlinger said. When it’s pointed out that Connolly and the FBI had 700 pages of documented paperwork outlining Bulger’s informant status, he said: “It’s full of information that’s not unique, where there are duplicate sources, sometimes from other informant files. The very definition of an informant file is one that is replete with unique information that directly leads to a prosecution.”

The film also airs a sequence with FBI agent Bob Fitzpatrick, who went to interview Bulger at his house to legitimise him as an FBI source for Connolly. “[Bulger] told me ‘I’m not an informant. I pay them, for information – not the other way around’,” Fitzpatrick said in the film. “At that point, I made a mental reservation: what am I doing here? What’s going on here?” It seems Whitey made a lot of people feel like that.

Was it because he was playing the game on a level that most people can’t even comprehend? It’s no secret that he was successful at what he was doing for a long time, but in the end, he lost. So what’s the difference? He will spend the rest of his days in a prison cell, but is that enough for a man who allegedly killed 40 people? At 80-something, he is in his twilight years, so in reality he is not paying that high a price. Only his legacy remains and few names have resonated more or been better associated with Boston than Bulger’s.

“Whitey is notorious for many reasons – he did time at Alcatraz, survived the Irish gang wars, corrupted J Edgar Hoover’s supposedly incorruptible FBI, became a Robin Hood figure to a South Boston neighbourhood reeling from the school busing crisis of 1970,” George Hassett, author of Gangsters Of Boston said. “But most important is the fact that his brother happened to be the most powerful man in Massachusetts for many years – State Senate President Bill Bulger. That’s just an accident of birth. Whitey is not a criminal mastermind, just a bully who understood how to manipulate others.”

Bill Bulger pictured with John Kerry
Bill Bulger pictured with John Kerry

For all his accolades, he was a very well insulated and protected gangster. “Whitey Bulger was better protected than any criminal,” the Boston mobster told us. “With the FBI on his right and a senator on his left, he was untouchable. Or at least he thought he was. But karma is a bitch and what you reap, you sow. So I say rot in hell, Whitey.”

Bulger’s history as the leader of the Winter Hill Gang, an Irish crime family that grew out of his Southie neighbourhood in Boston, is well known, as is his role as a top-echelon FBI informant who operated with lawless impunity for 20 years under the protection of his FBI handler Agent Connolly. The result was free rein for Bulger and top associate Flemmi, to manipulate Boston’s underworld to suit their own purposes and advance their own criminal enterprise ahead of La Cosa Nostra’s. The Feds often turned a blind eye and even encouraged the murders of rival Mafia and recognised crime figures. But when he was finally captured in 2011, people speculated about what card he might have up his sleeve to get out of the jam he was in. The Whitey mystique and mythology resonated and everyone in Boston figured he had an ace in the deck and was about to pull it out. The charges were stacked against him but if there was an out, Bulger would find it.

“When Whitey was first captured, many people in Boston compared it to the Red Sox winning the World Series in 2004,” Hassett said. “We couldn’t believe it happened. We figured he was dead or the FBI didn’t want to find him. The bombing of the Boston Marathon obviously is the big local story now, but Whitey’s court appearances were still news.” The media and the public were salivating at witnesses. His last and grandest trick on the biggest stage of all.

A courtroom sketch of Bulger
A courtroom sketch of Bulger

Hassett said: “People were wondering ‘who can Whitey give up in the FBI? The Boston police? The state police?’ If he does have law enforcement corruption to reveal, most of it would be barred by the statute of limitation. If Whitey told all, could he solve any of Boston’s gangland mysteries such as the Black Francis Massacre? The art heist of a Rembrandt painting at The Isabella Stewart Gardner Museum on Huntington Avenue?” In fact, Bulger didn’t say much at his trial except to mutter “I’m not a fucking informant,” when the litany of witnesses, mostly former comrades turned snitch themselves, described his relationship with FBI officials.

“It was a great show,” Hassett said about the trial that captivated Boston’s and the nation’s attention. Bulger’s infamy was on the big stage and he didn’t disappoint, posing question on top of question about his alleged co-operation with the government. But in the end, he lost and is now doing life in prison. Whether he was a snitch or not, he was a violent and brutal criminal who turned Boston’s gangland into a killing field for more than two decades.

He will live on in notoriety. That much is certain. Locked away in federal prison, the 80-something Bulger has been the toast of Boston and highlight of local talk radio shows and Hollywood alumni. As he serves his time, documentaries and films like Black Mass keep his name alive, romanticise his legend and add to his mythology. But to some it’s a wasted effort, because in reality who wants to glorify a snitch?

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