How Will the World Remember Gang Kingpin and FBI Rat Whitey Bulger?

Bulger's Alcatraz mugshot from 1959.

One of the most outlandish and depraved criminal careers in American history has whimpered to a close. And, to no one’s surprise, it looks like James "Whitey" Bulger is going to spend his remaining years locked up inside a prison cell.

On Monday, the jury in his trial found him guilty of a slew of charges, including 11 murders. It was a trial where everything Bulger did and did not do was noteworthy.

He did not take the stand. He did not drag down any federal agents who weren’t already implicated in allowing him to terrorise the Boston underworld for decades. He made no mention of his brother, Billy, who – as president of the former Massachusetts Senate – was one of the most powerful politicians in the state.

It was the final chapter in what has been a superlatively weird and notorious underworld saga.

This is a guy who, while incarcerated, was part of the government’s LSD testing program, Project MKUltra. He did time in Alcatraz, the notorious prison in San Francisco Bay. He survived a gang war. He dubiously and famously won the Massachusetts lottery. I’m not saying this as some sort of ham-handed metaphor – he literally won the lottery, splitting $14 million (£9 million) with three other men.

He killed, hijacked, pushed drugs and loansharked. He corrupted the Boston office of the FBI. For years, he was a federal informant, which allowed him to undermine his mob rivals and commit heinous crimes with impunity. Impossibly, he was both rat and kingpin. For years there was a pervasive myth that he was some sort of Robin Hood figure who kept the drugs out of his native South Boston. It was Boston provincialism at its lowest point.

A young Bulger.

He avoided capture for more than a decade. During his time on the lam he was the FBI’s bogeyman – a constant, taunting reminder of one of the agency’s darkest hours and biggest failures.

Whitey sightings were reported all over the world – in London, in Ireland, in Rome, in New York City, back in Southie. He was everywhere and nowhere. His myth grew.

People wondered aloud if the feds even wanted to catch him, given the amount of dirt he had on the shady agents that allowed him to run amok for years. Now he’s just another criminal who will spend the rest of his life behind bars.

Jane McDonald is a distant cousin of mine. She’s also the daughter of Joe McDonald, who was in the Winter Hill Gang with Bulger.

Joe never cared for Whitey, as Jane is quick to point out. Urban legend has it that her father allegedly remarked that Bulger felt the need to use machine guns in the hopes it would add inches to his dick. She says she can’t corroborate that, but does not rule it out, either.

She said her father would assess Whitey thusly: “He ain’t nothing.” He would then add, sarcastically, “He’s got connections.”

“He never liked him,” she tells me. “He never trusted him because he came to Winter Hill for protection, but he was turning on his friends.”

The arrival of Whitey in the Winter Hill fold – he had sought protection from the outfit after being on the losing side of a gang feud – saw the gang expand its operations, Jane tells me. Before, they were into bookmaking and armed robbery, she says. According to her father, Winter Hill only got into the protection and extortion racket after Whitey’s arrival in the early 1970s.

“The extortion turned his stomach, I think,” she says of her father.

After Whitey’s arrival, some of the associates started pushing – and doing – drugs, she says.

This being Boston, where everyone is related and interconnected to everyone, Jane is also a cousin of one of Whitey’s victims, Michael Donahue. (She also tells me I’m distantly related to him, something I was unaware of.)

An older Bulger with a baby goat.

Some of those marked for death by Bulger were underworld hoods themselves; Brian “Balloonhead” Halloran, for instance, was a South Boston coke dealer who turned into a federal witness.

Donahue, however, was not a criminal. The only thing he was guilty of was being in the wrong place at the wrong time. He was giving Halloran a ride home from Anthony’s Pier 4, a restaurant in what is now known as Boston’s seaport district, when Bulger opened fire, hitting Donahue in the head and killing him.

The Donahue slaying was one of the 11 murders Bulger was convicted of Monday.

Jane says she had no real reaction to the verdict – that she expected Bulger would be found guilty of a multitude of crimes and spend the rest of his days behind bars.

She also says that she has known Bulger killed Donahue for years.

“I don’t really have any feelings about it,” she says of the verdict. “He’s going to have the guards kissing his ass. He’s going to be a hero, a celebrity in jail. They ought to charge admission to see him. People would love to see the toothless tiger.”

McDonald fled greater Boston when she was 21; she didn’t want to have to fear getting shot in the back while walking down the street. When she was a child, the family did not have a car because they feared someone would rig it with a bomb after someone tried doing just that to her father’s close friend and associate James “Buddy” McLean.

“There was the whole Irish car bomb thing. That was a concern,” she says.

Now 59, disabled and living in Florida, Jane thinks Whitey gave her father up to the authorities on at least one occasion.

She suspects Whitey set him up with a bag full of machine guns when he was apprehended in New York City.

I ask her to sum up Whitey in one sentence. She needs only one word. “Sociopath,” she says.

Follow Danny on Twitter: @DMacCash

More stuff about James "Whitey" Bulger:

I Met Some Guys from Boston Who Really Hate James 'Whitey' Bulger My Cousin Joe Was a Hitman for the Boston Mob South Boston Is Too Ugly for Reality TV