The life and crimes of the late Boston crime lord, Whitey Bulger

In this feature from our archives Irish journalist, John Breslin, charts the rise and fall of the infamous Boston crime lord, Whitey Bulger, who was found dead in his prison cell earlier today.

The life and crimes of the late Boston crime lord, Whitey Bulger

DEBRA Davis’s relationship with her boyfriend of nine years was on the rocks when he invited her to a house in south Boston.

Stepping in, her much older boyfriend stepped aside as another man emerged from the shadows and strangled her to death.

After the murder, Davis’ teeth were pulled to make identification more difficult and her body taken to the banks of a river, where it was dumped in a shallow grave.

It would be 20 years before her body was found by the Neponset River in Quincy, south of Boston. It was only one of many found there after someone began revealing where all the bodies were buried, literally and figuratively.

Debra Davis’ alleged killer was James ‘Whitey’ Bulger whose federal trial on charges of running a criminal enterprise over three decades and being involved in the murder of 19 people is expected to begin on Monday following jury selection.

Her family had warned her about being involved with Stephen Flemmi. In the tight knit Southie community, the most Irish in the most Irish of cities, everyone knew everyone else.

And the family knew Flemmi was Bulger’s right hand man. And they knew he was a killer.

She was just 17 when she met Flemmi, then in his early 40s.

In 1981, aged 26, she was tiring of the relationship and wanted out. But she knew too much, according to Flemmi himself.

Specifically, she knew of Bulger’s links to the FBI. Flemmi had told her, in a fit of impatience after being paged by Bulger one evening. Bulger, it is alleged, ruled she must die.

Deborah Hussey was Flemmi’s step daughter. When she reached adulthood, she accused Flemmi of sexually molesting her as a teenager. She also had to die.

This from a court document, one of thousands now filed in connection with numerous criminal and civil cases stemming from the murderous activities of the now notorious Boston Irish mob and its connections to corrupt FBI and other law enforcement agents in Massachusetts.

“They murdered her in much the same way they murdered their other victims, by luring her into a house and strangling her. Here again, Bulger grabbed Debrorah Hussey from behind and scissored her neck between his forearm to crush her windpipe.

“Hussey fought desperately for her life and knocked Bulger over.

When the two fell to the floor, Bulger jack-knifed his body to work his legs around Hussey’s body to crush her torso.

"The court infers Hussey lost consciousness from asphyxiation and died in minutes.”

The teeth were extracted and the body buried in Quincy.

As Bulger waited for the trial that is set grip Boston over this summer, it appears those two murders are very much on his mind.

Of all his alleged criminal deeds, it is those two he wants to refute. “I never killed any women,” he wrote to a friend from his prison cell.

Debra Davis’ brother Steve certainly does not believe Bulger is innocent of his sister’s murder. Davis, who more than once has offered to kill Bulger and save the bother of a trial, was in court last week for jury selection and has vowed to be there every day of the expected three month trial.

He watched as the 83-year-old Bulger took his seat in the belly of the Boston federal court room.

“Good morning,” said Bulger to the first batch of some 675 potential jurors to be questioned ahead of the panel being whittled to 18, 12 seated and six alternates.

Looking fit, dressed in jeans, a navy jersey, white trainers and wearing wire rimmed glasses, his time in prison appears to have been good for his health.

In his first court appearance following his June 2011 arrest in Santa Monica, California, he looked dishevelled and every bit his age.


Bulger is accused in a wide ranging racketeering indictment of leading for nearly three decades the Winter Hill Gang.

He is alleged to either have been directly involved or ordered 19 murders, and directing a mob involved in extorting money from drug dealers, bookmakers and businessman.

From his headquarters at the South Boston Liquor Store on Old Colony Avenue and the Triple O’s Lounge on West Broadway, Bulger orchestrated the corruption of FBI and other law enforcement officials, the laundering of millions in cash and the stockpiling of an arsenal of weapons, according to prosecutors.

More than 150 potential witnesses, for the prosecution and the defence, have been listed in court documents.

Key to the prosecution case are three of Bulger’s one time henchmen, Flemmi, Kevin Weeks, the man who finally spilled all on the site where many bodies were buried, and John Mortarano, a cold blooded hit man who admits to murdering 20 people.

Between the three, they have admitted to being involved in a staggering 46 murders.

Each cut a deal with the Government. Flemmi is serving life in prison but avoided the death penalty. Mortorano is a free man after serving just a 12 year sentence, while Weeks served less then six.

Bulger didn’t cut a deal but he tried, according to Boston Globe reporters, Kevin Cullen and Shelley Murphy.

In their book, Whitey Bulger: America’s Most Wanted Gangster and the Manhunt That Brought Him to Justice, the authors reveal Bulger offered to admit to the 19 murders, even ones.

He also offered to submit to the death penalty in Oklahoma or Florida, where he is charged at state level with murder.

In exchange, he asked that his girlfriend, Catherine Greig, be spared prosecution and prison.

Bulger wrote in a letter from prison:

I never loved anyone like I do her and offered my life if they would free her – but no they want me to suffer – they know this is the worst punishment for my by hurting her.

Prosecutors refused the offer. Greig pleaded guilty to harbouring a fugitive and identity fraud and was sentenced to eight years in prison.

In his letter, Bulger complained: “Got me to live crime free for 16 years – for this they should give her a medal.”

Catherine Greig was the siste-in-law of Donald McGonagle, a mild mannered and popular figure in south Boston who was shot dead as he sat in his car at a traffic light.

McGonagle, it is alleged, was James Bulger’s first murder victim. And he killed the wrong man.

Gang war

The year was 1971 and south Boston was in the middle of bloody gang war between the Killeen and Mullen factions that lasted a decade and leave more than 60 people dead. It began with a petty row.

One of the leaders of the Mullen gang was Paulie McGonagle. Bulger belonged to the rival gang.

In his book, Kevin Weeks described what happened.

“One day while the gang war was still going on, Jimmy was driving down 7th Street in south Boston when he saw Paulie driving toward him. Jimmy pulled up beside him, window to window, nose to nose, and called his name.

“As Paulie looked over, Jimmy shot him right between the eyes. Only at that moment, just as he pulled the trigger, Jimmy realised it wasn’t Paulie.

It was Donald, the most likeable of the McGonagle brothers, the only one who wasn’t involved in anything.

Bulger drove to the home of one of the leaders of the Killeen gang, William O’Sullivan, who was at the stove cooking.

Weeks recalled Bulger telling O’Sullivan that he shot the wrong man, that he shot Donald.

“Billy looked up from the stove and said: ‘Don’t worry about it. He wasn’t healthy anyway. He smoked. He would have gotten lung cancer. How do you want your pork chops?’

Paulie disappeared soon after. Bulger is alleged to have been involved in his disappearance.

The gang war ended with victory for the Mullen faction, which was folded in to the Winter Hill mob, headed by Howie Winter.

Ever resourceful, Bulger, despite his connection to the Killeen group, managed to align himself with the victors, as did his crew of Matorano, Weeks and Flemmi.

Shamrocks gang

James ‘Whitey’ Bulger was born in Dorchester, Massachusetts in September 1929, the eldest son of James and Jean Bulger, nee McCarthy.

Five other children would follow, two boys and three girls.

In 1938, the family moved to Boston, to the Old Harbour Housing Project, one of the first large scale urban estates in the United States.

Bulger’s father had lost a leg in a workplace accident, had other health problems and through his life had difficult finding work.

But he did encourage his children to pursue an education. And, in the case of two of his boys, William and John, it worked.

William became Massachusetts’ most powerful politician, John spent his working life in the court service.

But the eldest embarked on an entirely different path, never attending secondary school, preferring life on the street, including as a member of a gang called the Shamrocks.

Bulger, who developed a reputation for his fighting skills, committed his first known offences as a young teenager. He was eventually arrested for theft and assault and sent to reform school for a period.

In 1948, he joined the air force and, despite spending time in the stockades for brawling, was honourably discharged in 1952.

Bulger went straight back to crime.

He embarked on a spree of bank robberies in his home state, Rhode Island and as far away as Indiana.

In 1956, aged 26, Bulger was caught and sentenced to 10 years in federal prison, serving his time in various penitentiaries, including the notorious Alcatraz.

Letters home to his brother William and mother reveal deep families bonds – and his vow to settle down and avoid crime when he returned home.

In one letter he urges his brother to pursue a career in politics as it “pays a good salary” and a “pension.”

While Bulger was serving his time, William Bulger was first elected as a state representative.

During his time in prison, he agreed to take part in a CIA experiment where inmates were given LSD in return for a slightly shorter sentence.

He claims those experiments are responsible for recurring nightmares.

On his release in 1965, he returned to south Boson and went to work as a janitor at a court house. But he was also acting as an enforcer for local mobsters and deeply involved in the gang war.

And he had a son, Douglas Cyr, who died in 1973 aged six following a severe allergic reaction to aspirin.

“He changed after Douglas died,” said Douglas’s mother, Lynsey.

He was colder.

It was just after Christmas 1976 when mob connected strip club owner Richard Castucci was shot in the back of the head as he sat counting money in a Boston apartment.

The shooter was John Matorano. Also present were Bulger and Flemmi. They cleaned up the mess, according to Flemmi and Matorano.

Castucci was a high level FBI informant and he had told the agents of the hiding place of two on the run members of the Winter Hill gang.

The reason Bulger and his crew knew Castucci was an informer was because they were told by a Boston-based FBI agent named John Connolly. That indictment is one of several handed down against Connolly over the last decade.

Following the murder, Connolly directed investigating agents away from Bulger, telling them the execution was not in the style of the Winter Hill gang.

In 2009, Castucci’s family won a more than $6m lawsuit against the federal government for its agents involvement in the murder.

Connolly, currently serving a 40-year sentence for his involvement in a murder in Florida carried out by Matorano, has always insisted that he was not corrupt but that Bulger and Flemmi were his informants.

It is a claim that Bulger denies and claims to want to prove in court. But there is a contradiction at the heart of Bulger’s defence.

On the one hand, Bulger, in his letters, is claiming he was never a government informant. On the other, his lawyer has strongly indicated that one of the planks of his defence will be that Bulger was granted blanket immunity from prosecution by government agencies in return for information.

Whatever happens the actions of law enforcement agencies, particularly the FBI, will come under heavy scrutiny.

One of the witnesses being called by the defence is none other than the head of the FBI, Robert Mueller.

Already, relatives of those killed allegedly by Bulger’s gang have won significant amounts of money in civil actions after claiming their loved ones died because of the actions, or lack of, of the FBI.

And it was not just John Connolly, it has been argued in repeated court cases. He was able to continue to operate even though he was known to have a close, likely corrupt, relationship with Bulger

Others in the Boston FBI office took money from Bulger. His tentacles also stretched to other law enforcement agencies including the state police.

Bulger, on his way to taking over full control of the Winter Hill mob, met Connolly, the son of a Galway immigrant, graduate of Boston College and Harvard University, in 1975.

Unlike in the film the Departed – the Jack Nicholson and Matt Damon characters are loosely based on Bulger and Connolly – the mob boss did not cultivate the younger man from child hood.

According to Matorano, they were, in fact, introduced by Bulger’s younger brother, William, then a rising political star. William Bulger, the long-time former speaker of the state senate and later head of the state university, denies this.

However they met, it was to be the start of a fateful relationship that led to Bulger and his cohorts essentially being able to act, and kill, with impunity.

Bulger, it is claimed, was recruited as an informant to help bring down the Italian Mafia in Boston. But the two decade relationship appears to have benefited Bulger much more than the FBI.

When Roger Wheeler, a respected businessman, was shot dead as he left an exclusive country club in Tulsa, Oklahoma in 1980, no one knew where the bloody trail would lead.

Colleagues reported being baffled as to why such a fine guy was murdered. The trail was certainly bloody, in large part because Wheeler had become unwittingly embroiled with the Boston Irish mob.

And it was John Matorano who pulled the trigger, he claims on the orders of Whitey Bulger, by then undisputed leader of the Winter Hill gang following the jailing a year earlier of Howie Winter.

Key Witness

Matorano was the key prosecution witness in the murder trial in Florida of John Connolly, later convicted and sentenced to 40 years in prison.

Connolly was convicted of being centrally involved in the 1982 murder of John Callahan, a gambling industry executive with close ties to the Boston mob, whose bullet ridden body was discovered in the boot of a car parked at Miami Airport.

A dime left on his chest signified he had been killed because he was, in gangster speak, a “rat”.

Not surprisingly it was Matorano who carried out the execution of his one time friend.

Matorano told a Florida court that he and an accomplice picked up Callahan.

Martorano told the court:

He got in the front seat, I got in the back seat... and shot him. I believe once, possibly twice.

The next morning, while transferring the body to the trunk of Callahan’s Cadillac, Martorano said, he and his accomplice thought they heard him moaning, so they shot him several more times.

Callahan’s path to death began with a business deal with Wheeler. They set up a gambling enterprise in Florida together.

Callahan was soon ousted after an investigation revealed his close connections to the Boston mob and that he was skimming money from the company. He made several attempts to buy the company back but was rebuffed by Wheeler.

It was then, according to prosecutors, he decided Wheeler had to die.

Naturally, he turned to Bulger, who dispatched his ace enforcer, Martorano, to carry out the hit in 1981.

According to FBI documents, within a month of Wheeler’s murder the trail had led to Callahan. The FBI in Boston was asked to follow up. Connolly, the agent with the top contacts in the Irish mob, was given the job.

Bulger had no information but Flemmi told Connolly — according to the agent’s official report — that Callahan had drifted away from the Boston mob and was reduced to hanging about with a small time hood called Brian Halloran.

Connolly questioned Callahan, who denied any involvement with the gambling syndicate or the death of Wheeler. However, two other FBI agents in Boston, who did not trust Connolly, were separately in contact with Halloran.He had a story to tell of a meeting with Bulger, Flemmi and Callahan, during which the murder of Wheeler was discussed.

Halloran wanted into the witness protection programme. Records show the FBI in Boston limited distribution of Halloran’s information and that Connolly was not on the list of those who needed to know.

One of Connolly’s superiors — who later admitted taking money from Bulger — let slip to the rogue agent that Halloran, a small time coke dealer, was co-operating with authorities.

Bulger and two associates shot dead Halloran in broad daylight on a Boston street in May 1982. Halloran’s friend, Michael Donohue, entirely innocent but in the wrong place at the wrong time, was murdered with him.

The authorities turned their attention once again to Callahan.

Martorano claims he was summoned to a meeting in New York with Bulger and Flemmi, and there he was ordered to kill Callahan.

At the meeting, Martorano said, Bulger told him that Connolly had warned the gang that the FBI planned to pressure Callahan for information about the Wheeler killing.

Bulger told Martorano that the message from Connolly was that Callahan was “going to fold and we’re all going to end up in jail for the rest of our lives if he doesn’t hold up”.

That was the end of Callahan.

“The defendant is a corrupt FBI agent,” prosecutor Fred Wyshak told jurors at Connolly’s 2008 trial.

“He gave sensitive information to gangsters who used that information to protect themselves from investigation and prosecution and used that information to kill people — and one of those people was John Callahan.”

Fall guy

For his part Connolly maintains he is the fall guy for the FBI’s mistakes, and the people killed as Bulger and his crew were essentially allowed to act with impunity. From his prison cell, Connolly is likely to be keeping a close eye on the Bulger trial as his lawyer has said he will appeal if Bulger tells the court he is innocent.

When Bulger was recruited as an FBI informant, he did so on the condition that his links to the IRA and gun running would not be investigated, according to authors Cullen and Murphy.

And Bulger later met Provisional IRA leader, Joe Cahill, who was smuggled in to the US for a meeting that took place in the Triple O’s lounge. According to Kevin Weeks, Bulger idolised Cahill and readily agreed to smuggle guns to Ireland.

In 1984, John McIntyre was taken to a “house of horrors”, tortured for eight hours, including repeatedly strangled to near death, before being shot dead.

McIntyre was a mechanic on the shipping trawler, Valhalla, the boat used to smuggle seven tonnes of weapons to the IRA. Off the Irish coast it met and off loaded the arms to the Marita Ann, and its crew, including Martin Ferris, the now Sinn Féin TD.

The Valhalla made its way back to Boston but the Marita Ann was intercepted.

Picked up on an unrelated charge, McIntyre started talking – and reportedly implicated Bulger in the gun running operation. Some one in law enforcement tipped off Bulger. That was the end of McIntyre. He was delivered to Bulger and murdered, tortured, his body buried and not recovered for 15 years.

His brother Christopher’s voice drips with contempt when he talks about ‘Whitey’ Bulger.

“I have no respect for this man. Many people think he’s intelligent. But when your friends are morons, you look pretty smart,” said McIntyre, whose family were awarded more than $3m in a successful law suit against the government.

“By the time we met it was too late.”

Bulger wrote in a letter from prison.

I was in too deep, had done too much to even consider an honest way of life.

He was speaking of Catherine Greig, whom he met in 1975 and went on the run with two decades later. Bulger described his 16 years as a fugitive as the happiest of his life.

“Became a real citizen and became a different person, experienced emotions, feelings that I’d shut down for years,” said Bulger.

A real citizen living in an apartment with a large stash of guns and $800,000 in cash when he was finally arrested. Still a “stone cold killer,” says Kevin Weeks.

Bulger went on the run in 1995 after being tipped off by Connolly he was about to be arrested on a racketeering charge under the RICO Act. The murder charges were added after Weeks and others began to talk in the late 90s.

For years he was one of the country’s most wanted, behind only Osama Bin Laden for much of that time.

The alleged mass murderer who used terror to control the streets of south Boston, all the time protected by the FBI, was realistic about his prospects and said he believed he would be convicted and would die in prison.


JAMES ‘Whitey’ Bulger topped the FBI’s Top Ten Most Wanted for more than a decade — second only to Osama bin Laden.

Born James Bulger on Sept 3, 1929, in Dorchester, Massachusetts, he was one of six children born to Roman Catholic Irish-American parents.

Whitey (so-named for his white-blond hair) grew up in a South Boston public-housing project. His father worked as a longshoreman on the docks. Bulger was a troublemaker as a child, and even lived out the childhood fantasy of running away with the circus when he was 10.

He was first arrested at age 14 for stealing, and his criminal record escalated from there. As a youth, he was arrested for larceny, forgery, assault and battery, and armed robbery and served five years in a juvenile reformatory.

On his release, he joined the air force where he served time in military jail for assault before being arrested for going AWOL. He received an honourable discharge in 1952.

His criminal career took off when he returned to Boston. In June 1956, he was sentenced to 25 years in federal prison. He ended up serving nine years, and then returned to Boston to resume his life of crime.

Bulger became an enforcer for crime boss Donald Killeen.

After Killeen was gunned down in 1972, Bulger was consolidated into the Winter Hill Gang, where he quickly rose through the ranks. A shrewd, ruthless, cunning mobster, Bulger sanctioned numerous killings.

By 1979, Whitey Bulger had become a pre-eminent figure in Boston’s organised crime scene. That year, Howie Winter was sent to prison for fixing horse races, and Bulger assumed the gang’s leadership.

Over the next 16 years, he came to control a significant portion of Boston’s drug dealing, bookmaking, and loan sharking operations.

Under his reign, more than 18 murders accumulated in all.

At the same time, unbeknownst to even his closest associates, Bulger was an FBI informant.

Taking advantage of his brother William’s stature in the State Senate and childhood friendships that linked him to members of the police force, Bulger helped bring down Boston’s Italian-American Patriarca crime family while simultaneously building a more powerful and arguably more violent crime network of his own.

Jack Nicholson’s character in Martin Scorsese’s 2006 Academy Award-winning film The Departed was loosely based on Bulger.

In the spring of 1994, authorities launched an investigation into Bulger’s gambling operations.

In early 1995, Bulger and his associate, Stephen Flemmi, were indicted. Bulger, however, managed to slip through the authorities’ grasp.

According to federal sources, Bulger’s FBI handler, longtime friend Special Agent John Connelly, tipped Bulger off to the 1995 indictment, allowing Bulger to flee with his common law wife, Theresa Stanley.

She soon returned to her family and Bulger took up with a girlfriend, Catherine Greig.

Until his arrest in 2011 he was living in plain sight in California with Greig. The two had lived quietly in a Santa Monica apartment packed with weapons and cash.

They were arrested after Boston FBI Special Agent in Charge Richard DesLauriers launched a media campaign that included pictures of Greig as well as Bulger.

Bulger was accused of committing or ordering the murders while he ran Boston’s Winter Hill crime gang.

He also faced charged of racketeering and extortion. Bulger plead not guilty but was convicted and sentenced to what ultimately proved to be a life sentence in prison.

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