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blind eye The U.S. State prosecutor who took down Whitey Bulger and exposed mobster as an FBI informer


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Bulger shortly before he disappeared in 1995.

Bulger shortly before he disappeared in 1995.

Whitey with his pet

Whitey with his pet

FBI wanted poster

FBI wanted poster

Bulger’s passport photo

Bulger’s passport photo

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Bulger shortly before he disappeared in 1995.

Boston gangster James 'Whitey' Bulger's role as an FBI informant is a lesson for police forces across the world in how NOT to handle their touts.

Brian Kelly, the former US state prosecutor who was the lead counsel against Bulger, tells this week's Crime World podcast that the mobster murdered at will, often using information leaked to him by his handlers.

He believes the corrupted system that allowed such a high-level criminal inform on others while operating with virtual impunity is one of the greatest scandals in the history of law enforcement.

Kelly pushed hard during Bulger's high-profile trial to make sure evidence of his informer status was heard, and the prosecutor says that at times the mobster was more defensive about this than he was regarding the multiple murders he was accused of.

He says that he believes Bulger fought harder to save his reputation as an underworld heavy than he did for his freedom, knowing he would be under serious threat in prison as a known tout.

Kelly, who is one of the most respected lawyers in the US, tells the extraordinary story of Bulger during the podcast interview from his native Boston, where he now works for one of the city's top legal firms.

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Bulger’s prison photo.

Bulger’s prison photo.

Bulger’s prison photo.

He says while he prosecuted plenty of gangsters and criminals in his time, none were more menacing than Bulger, who was 81-years-old by the time he reached the dock.

"He was an old man at that time in 2013. But his demeanour was every bit as menacing as it had ever been. He was scary and there was an aura of viciousness about him. He gave off this thing that he was not to be trifled with and I was glad to have the marshalls nearby. He may have intimidated some of the jurors but I knew that he was no real threat.

"There were no guns in the courtroom, it wasn't as if he was going to be able to shoot anyone, but he would watch up to the judge and it felt like a lion stalking his prey," Kelly says.

Whitey grew up in an area of Boston known as 'Southie', predominately populated by Irish Catholics.

Growing up, he joined the local 'Winter Hill Gang' and worked first as an enforcer before eventaully taking over the crew, who were known as the Irish mafia and who had a fearsome reputation for extortion and gambling rackets as well as drug dealing.

Bulger was caught a number of times committing crime and spent time in prisons including Alcatraz, but he gained notoriety for being the most vicious of all the crime bosses in the area and beyond.

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Former Federal prosecutor Brian Kelly.

Former Federal prosecutor Brian Kelly.

Former Federal prosecutor Brian Kelly.

"Bulger and his closest associates carried out crimes hands-on. A lot of the local mafia guys would have buffers or underlings to do their dirty work but not Bulger. He liked to get his hands dirty," he tells Crime World.

"Bulger and a few of his select crew members, they were a ruthless bunch and even the Italian mafia was afraid of them."

Bulger's mother was a first generation Irish immigrant and his father was a Canadian. Whitey had two brothers, both of whom excelled at school, and one, Billy, went on to become a powerful politician.

But while his siblings forged careers for themselves in the legitimate world, Bulger felt more at home on the streets and by the 1980s he was totally in charge of his turf and was making a fortune from all sorts of criminal ventures.

"The people he shook down for money were easy prey. They were running illegal gambling businesses or dealing drugs and they couldn't come looking for help. Bulger and his crew would confront them and everyone knew it was better to pay than to die," he said.

Bulger's rules were set in stone - nobody crossed him and nobody grassed. But as it would later emerge, the hypocritical gangster was operating as an informant himself and being handled by an old childhood friend - crooked FBI agent John Connolly, later convicted for racketeering.

Bulger was tipped off by Connolly and others in the FBI when information came in about his role in crimes and he would often then torture and kill the 'informant'.

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In his younger days

In his younger days

In his younger days

He went on the run in 1995 when he was tipped off that he was set to be charged in relation to organised crime, and remained in hiding for 16 years until he was caught in Santa Monica, California, where he had been living under an assumed name.

When he eventually went on trial in 2013 it was his status as an informant that took centre stage, aside from the 19 murders he was accused of.

"Part of the grotesque irony of his success was that he had informants killed when he was one for many years," says Kelly.

"He used the FBI as they used him. Nobody suspected he was informing along the way as it was too ridiculous to consider. He was a homicidal maniac, running organised crime in Boston and it would have been preposterous to believe he was also working with the FBI but he was."

While Kelly says he totally understands how law enforcement has to work with criminals and that intelligence gathering is key to solving crimes, he said that in the case of Bulger, the FBI had got into bed with the kingpin.

"The problem was that instead of getting information from low-level figures to bring down the big bosses they were getting information from the big bosses. Because of the information they gave him back, people were killed, he says.

"These things have a serious cost when not handled properly and that is why all these protocols are in place. But people can get lax and bureaucracies and the institutions get lax and sometimes the institutions are more concerned about their own reputation than they are about individuals and justice.

"In the case of Bulger, the FBI became more concerned about bad press than the fact that their informants had run amok," he said.

Kelly and his team secured two life sentences plus five years for Bulger after putting up a legendary case against the mobster in 2013. When he went to jail he found himself unpopular and he failed to make friends or gain any protection.

At 89 years old in 2018 Bulger was beaten to death in his wheelchair, his eyes and tongue gouged out in a brutal and slow murder carried out by suspected mafia underlings.

"He found it very hard in court to deny being an informant. But we fought hard to introduce the proof that was there. We weren't going to allow that to be ignored or denied and it helped tell the story to the jury. In a way he was resigned to the fact that he had lost but he did spent the trial trying to focus on things he felt made him look better, like denying he had killed women and denying he had worked with the FBI.

"In the end, he was savagely beaten to death. It wasn't a good way to go. It was a savage way to die but the fact is that not a lot of people felt bad about it. One of the main takeaways for me is that it is not a problem to use informants for certain things but you always have to be careful around them.

"They can not be left alone or law enforcement cannot look the other way and let them do what they want. He should have been shut down long before he was and thrown in jail where he belonged and that would have saved a lot of lives and a lot of mayhem for the city of Boston."

  • Crime World is available on Soundcloud, Acast, Apple and all podcast platforms.

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