Tom Foley of the Massachusetts State Police races through Boston’s streets toward Dorchester, the city’s organized crime unit commander at the wheel. An informant has just given him the tip he has waited years for. In the cold night air beneath a busy highway, he makes a grim discovery: a mass grave. The work was brutal, slow, miserable.
On a freezing night, on his hands and knees, he had to pull each bone out of the earth, lifting the remains of three individuals stacked on top of one another. A woman’s skull comes up. Her teeth have been ripped out, a gruesome tactic meant to make identification impossible. Foley suspects these bodies belong to men and women missing and presumed dead for more than two decades.
Strangled, shot, left to rot in an unmarked grave. And Foley knows in his gut who is responsible. A man he has been tracking for twenty years. An Irish-American mobster with a deadly grip on Boston.
A lot of people didn’t know what he looked like, but they knew who he was. His name was like the local boogeyman. Crime boss and vicious killer James “Whitey” Bulger. In the 1950s, South Boston is a violent neighborhood ruled by powerful criminals.
Gangs with dramatic names like the 40 Thieves or the Drip and Daggers control the streets. Running with these gangs is a young thug named James Bulger. His blonde hair earns him the nickname Whitey. He grows up on the lowest rung of the neighborhood, in one of America’s first housing projects.
His family qualified because his father had lost an arm as a young man and struggled to support them. Whitey grew up poor, and Whitey hated being poor. In his teens, he makes a name for himself on Southie’s mean streets. He was a tough kid who never backed away from a fight, a savage fighter.
He starts his criminal career stealing cargo on Boston’s waterfront. Trucks would come in with goods, and there was an organized group stealing from them. They called it tailgating. Whitey was part of it.
In his twenties, Bulger steps up to bank robbery. He robbed banks in Massachusetts, Rhode Island, and Indiana. But at twenty-six, the underworld delivers a harsh lesson. Bulger gets ratted out by one of his own gang and receives a twenty-year sentence, including three years in Alcatraz.
The experience had a huge impact on him. He never wanted to go back to prison again. When he comes up for parole, Bulger puts on his best behavior and convinces the board he has gone straight. On March 1, 1965, the thirty-five-year-old walks free after serving only nine years.
But this gangster has no intention of turning over a new leaf. He gets back into it quickly, aligning himself with local gangsters in South Boston. For four years, Bulger works as an enforcer for an Irish gang called the Killeens when a mob war breaks out. Another Irish gang, the Mullens, are muscling in on Killeens territory.
One day, Bulger sees a car belonging to a Mullens boss. In broad daylight, he steps out of the shadows. By the late sixties and early seventies, he had an amazing reputation as a brutal, cold-blooded killer. But killing isn’t enough for Bulger.
He was incredibly ambitious. He didn’t just want to be anybody. He wanted to be somebody. After his boss dies in a revenge killing, Bulger pledges allegiance to one of Boston’s biggest gangs, the Winter Hill Gang.
And that’s where he meets a kindred spirit. Through the Winter Hill Gang, he becomes associated with a gangster named Stephen “The Rifleman” Flemmi. Like Whitey, he had no problem killing people. Flemmi was a marksman in the Korean War.
Within months, he and Bulger are inseparable. They trusted each other and formed a friendship that lasted through the years. His partnership with Flemmi brings out the worst in Bulger. Together, they deal brutally with anyone who steps out of line.
When Bulger discovers he has a rat in his midst, he takes action. An informer is the lowest form of being. Things get violent in a second when you start talking rats and informers. Bulger lures a bookmaker he suspects of talking to the FBI to an apartment.
The gang’s money is counted out. Then Bulger gives the nod. They would track you down, dispose of you, and not even think about it. Then, in 1979, the Winter Hill Gang is suddenly brought to its knees.
Howie Winter, the leader, and twenty-one of his associates are busted by the feds for fixing horse races along the Eastern Seaboard. But not everyone in the gang gets locked up. The two members who were not indicted, the only two, were Whitey Bulger and Steve Flemmi. Fifty-year-old Bulger quickly seizes control of the remaining gang.
Two years later, the other major crime family in Boston, the Angiulo Mafia family, are also busted. That leaves the Winter Hill Gang as the most feared crime gang in Boston, and Bulger as its boss. Twenty years after Bulger first returned to the streets of Boston, the city is finally his. He could wake up in the morning, look across the water at the Boston skyline, and say, “I own this place.
”
Bulger wastes no time making a killing from his empire. They were making money from bookies, from drug dealers, and shaking everybody down in town. To bring in more cash, he leans on other criminals. Every drug that came into South Boston at the time had to go through Bulger, and he took large pieces of the profits from the drug distribution.
Soon, innocent people get caught in the crossfire of Bulger’s brutal power plays. Like thirty-two-year-old truck driver Michael Donahue. He stopped into a bar for a beer and ran into an old friend who needed a ride home. Bulger was targeting that friend.
They opened fire on the car and killed an innocent father of three whose only crime was giving his friend a ride home. Even those closest to Bulger and Flemmi aren’t safe. There was a girlfriend of Stephen Flemmi they were concerned about. She knew too much and was a liability.
They decide to make sure she’s never tempted to rat. So Flemmi brings his girlfriend home, and Bulger is allegedly there waiting. After strangling her, it’s said Bulger orders Flemmi to pull her teeth out with pliers to prevent identification. If somebody was a threat, they had to go.
Sergeant Tom Foley has served the Massachusetts State Police for fourteen years. He wanted to be part of what many think is the finest law enforcement agency around. Foley knows all about Bulger’s activities. Whatever crime could make money in Boston, that’s what Bulger was doing.
He was a one-man crime wave. For Foley, the failure to catch the crime boss is a stain on his beloved police force. As head of the State Police’s Special Service Division, he vows to rid Boston of Bulger. Tom was the right guy at the right time for this.
He was not from Boston. He’s a Worcester guy, growing up fifty miles away. He just saw Bulger as a bum and a criminal. Foley’s team gathers evidence to build charges against Bulger.
A garage in the North End of Boston, known to be used by Bulger, is put under surveillance. They spend weeks filming and photographing Bulger and his associates coming to see him. But the surveillance produces no evidence to bring charges. Every time the police are ready to close in on Bulger, the case mysteriously breaks down.
If there was a bug, he found out about it. If there was an investigation, he knew about it. If someone was cooperating against him, they were dead. Bulger and his gang are untouchable.
Ever since his release from prison twenty-nine years ago, the cops haven’t been able to pull him in on any charges. So Foley comes up with a dangerous plan: use Bulger’s criminal contacts to bring him down. First, he leans hard on Boston’s illegal sports bookies to snitch. A lot of them have been squeezed and shaken down by Bulger and Flemmi over the years.
But Foley knows getting them to turn on Bulger will be tough. They all know what the boss does to rats. Foley keeps up the pressure, wiretapping their phones and threatening them with jail time. Then he turns up the heat another notch.
They raided the bookmakers’ homes, threatened to indict them and their wives. They pressured them, and they cracked. Foley has done what no law enforcement agency has accomplished before. He has people willing to rat on Whitey Bulger.
They get enough information to charge Bulger and Flemmi with extortion. Extortion is a federal charge, so Foley brings the FBI into the manhunt. The feds agree to charge Bulger, but on one condition. They insist that they will make the arrest.
As a consolation prize, Foley and the State Police are tasked with arresting Stephen Flemmi. Officers keep an eye out for Bulger’s right-hand man. There’s a sighting of Flemmi in a restaurant in downtown Boston, and not long after, he’s in police custody. Foley radios the FBI to tell them he’s got Flemmi.
The feds haven’t a moment to lose. They know it’s going to get out, and it’s going to be on every television station in the city. Now is the time to take down Bulger. Foley wants to hear that Whitey has been arrested.
Instead, he gets a kick in the teeth. Bulger is nowhere to be found. Foley and his team scour the city, but it looks as though the crime boss has been tipped off and skipped town. When they went to Bulger’s girlfriend’s house, he wasn’t there.
He had already fled. At the time of Flemmi’s arrest, Bulger is in his car with girlfriend Kathy Greig, driving back to Boston when they hear that Steve Flemmi has been arrested. He turned around, and that was it. Bulger’s escape leaves Foley with one question burning in his head.
Who on earth keeps tipping Bulger off? With Bulger and Kathy Greig on the run, Flemmi rots behind bars waiting to be charged with racketeering. Two years later, Flemmi makes a last-ditch bid to avoid conviction with a shocking revelation. He decides on a very unusual strategy: admit that he and Bulger were informants and claim the FBI had promised them immunity.
The mobster claims that for more than two decades, he and Bulger have been informants protected by the agency. The claim sends shockwaves through the Massachusetts State Police. The FBI are forced to admit he’s telling the truth. Bulger and Flemmi had been working with the feds for more than two decades to help bring down the Italian Mafia.
There were these cozy little dinners where FBI agents sat down with Whitey Bulger and Steve Flemmi. One agent testified it was like Whitey was part of the team. The secret relationship explains how Bulger rose to power so quickly and how he was warned about his potential arrest two years earlier. The news comes as a sickening shock to Tom Foley.
These were top-echelon informants, two murderers killing people around Boston, and they were being protected. But it also gives Foley an unexpected break. Now the world knows Bulger and Flemmi are dirty squealing rats, and their criminal associates aren’t too happy about it. South Boston criminals would view what Bulger did as far worse than engaging even in murder.
To be a rat, there’s nothing worse than that. For Bulger’s contacts, it’s payback time, and they deliver in spades. New informants come forward with the precise location of eight victims of Bulger’s reign of terror. They go to a burial ground on a freezing cold night and pull out the remains of three individuals stacked on top of one another.
The bodies found include Flemmi’s girlfriend, who had disappeared fifteen years earlier. It’s final proof of what a homicidal monster Bulger is. The bodies showed he wasn’t just a guy who sat around South Boston shaking people down. He’s a guy that murdered people.
Bulger fled to avoid an extortion charge, but now he’s wanted for multiple murders. If they ever catch Whitey, he ain’t ever coming out. With this bombshell, the FBI finally ditches their informant and decides to take him down. They add Bulger to their Ten Most Wanted list the same year as an international terrorist named Osama bin Laden.
But there’s no sign of Bulger for six months. Then one day, the FBI gets a call from a hairdresser in California. She thinks she has just cut Kathy Greig’s hair. The sighting is at a hairdresser’s in Fountain Valley, a small city in Southern California’s Orange County.
The hairdresser called in and said, “I just cut that woman’s hair. ” And there was an older guy sitting outside waiting for her in a car. The descriptions appear to match Greig and Bulger. The FBI’s LA office wants to move on what they believe to be a credible lead and releases a statement saying a reliable sighting appears to have occurred.
But the Boston FBI are not convinced. Within twenty-four hours, in a confusing and convoluted way, the Boston office puts out a press release saying there was a possible sighting but it’s not confirmed. That response angers many in Boston who feel the FBI isn’t working hard enough to catch this notorious killer. The FBI, a three-billion-dollar annual budget with eleven thousand agents, had one agent specifically tasked with finding Bulger.
Just one. This was 2000. This was not an all-out search. Then in early 2001, new officials at the FBI make a strong public commitment to the Bulger manhunt.
They had no stake in the past corruption, and it would be a credit to their careers to be part of it. The feds reach out to Foley and his team about working together. Foley and his group felt there was a determination to make it one unit involved in the manhunt. But Foley isn’t happy with the agency’s idea of collaboration.
Instead of working together, it was more of a situation where they expected his team to work for them. He feels he has no choice but to turn them down. Tom believed the FBI had compromised previous investigations, but he was always willing to rise above that and hope the next group of FBI people were as committed as him to getting Bulger. He constantly had his heart broken.
That means the two forces will continue their separate investigations. You have to have the FBI and the Massachusetts State Police working with each other. It’s just not good. The only thing that’s good for is criminals.
Foley and his officers continue to stalk Bulger. Calls regularly come in with new leads. Some good information came from time Bulger spent in New Orleans. They had a little information about Florida.
Some tips put him even further away, with thoughts of islands in the Caribbean. There was information that he was spotted in South America, and claims he slipped over the border into Mexico to buy medicine. Foley’s team and the FBI travel the world looking for him. They would run down each lead until they found the person the tipster thought was Whitey, only to discover it was someone else.
These sightings continue to come in, and just one may be the one to crack the case. But the 9/11 terrorist attacks in New York force the FBI to move focus away from Bulger. 9/11 affected Whitey’s life on the run in a couple of ways. Whatever resources the FBI was committing to the Bulger manhunt and others, a lot got reallocated to the war on terrorism.
If Bulger is abroad, 9/11 has made it even more likely he will remain abroad. Travel became difficult after 9/11, with positive IDs and much more scrutiny. His team knew it was risky for Bulger to move around like that, so they felt he had hunkered down in a location he felt comfortable in. In September 2002, a tip comes in to the FBI that puts Bulger and Greig three thousand miles away from Boston, on the other side of the Atlantic.
There were rumors about Ireland, England, and Europe. A man claimed he saw Whitey walking through Piccadilly Circus with a shopping bag. He was very specific. He saw him, even yelled to him, and Bulger pretended it wasn’t him and kept walking.
The FBI send agents to London to investigate. The reason they gave it so much credibility is this guy had met Whitey before, when Whitey was visiting at the Meridian Piccadilly in 1994, before he was a fugitive. The London lead starts looking promising. With the help of Scotland Yard, the FBI find a safety deposit box in a London bank with Whitey Bulger’s name on it.
They found fifty thousand dollars in the box and focused a lot of energy there, spending a lot of time going over to London. But there’s no sign of Bulger anywhere, and the trail goes cold yet again. In 2004, Tom Foley retires from the State Police and gives up the chase. But he is constantly haunted by his failure.
Anytime he went out anywhere and people knew who he was, the Whitey Bulger jokes would start. He’d walk into a room and everybody would say, “Where’s Whitey? ” Bulger and Greig have now evaded capture for nine years. They have been perfect fugitives.
The key is to cut all ties, and the second key is to settle down somewhere and not move around. Unbeknownst to law enforcement, they’ve been living a quiet life completely under the radar in an unknown location. They spend a lot of time in their apartment, go out in the morning for walks, go out at dusk for walks. They’re having a good life.
They’re enjoying themselves. They can live incognito because they don’t look like wanted fugitives. When people think of a Ten Most Wanted gangster, it conjures up someone nefarious and scary-looking. Whitey just wasn’t scary-looking.
As the years pass, he ages, giving him the perfect disguise of anonymity. He looked like somebody’s grandfather with a nice woman by his side. He did not attract attention. But behind closed doors, he still lives on his gangster’s instincts.
He’s up on the third-floor apartment with binoculars, looking out at night for anything suspicious. Whitey was always good at surveillance and knowing if he was being followed. Many are now starting to wonder if Bulger will ever be found. He was either going to die out there or get captured because something lucky happened.
It’s not about master sleuthing. It’s about catching a break. It’s been fifteen years since Bulger fled Boston and became a fugitive. Frustrated and determined, the FBI call in the US Marshals.
This was always a point of contention. Even when they expanded the task force to include other agencies, nobody from the US Marshal Service was included. While not relinquishing control, the FBI allowed the US Marshal Service, the experts in fugitive searches, to become part of the task force. The internationally renowned US Marshals capture tens of thousands of fugitives every year.
This is what the Marshals do. They find fugitives. That’s what they are best at. The Marshals assign Neil Sullivan, a man who spent his career tracking fugitives and brought a fresh approach.
Sullivan joined the US Marshal Service in 1995, the same year Bulger went on the run. Being a Massachusetts native, he was very familiar with the Bulger case. It was a big story in the Northeast. Sullivan knows he has a massive task ahead of him.
He’s fully aware that for fifteen years, a lot of highly respected investigators had searched for Bulger without success. On his first day, Sullivan is shocked by what he finds in his office. It was just him, an FBI agent, and a clerk. In terms of full-time resources, it wasn’t a major commitment to finding Whitey Bulger.
The office may be understaffed, but Sullivan discovers thousands of files bursting with data. He reads for ten months. The number of associates was unbelievable. Bulger had a very wide range of people he was associated with.
Sullivan sifts through decades of case files. Together with the FBI, he builds a profile of where the fugitives may be hiding. He concludes that Bulger can’t be abroad. He had safety deposit boxes in Europe, and none were accessed during his time as a fugitive.
If he had really made it to Europe, he would have accessed them. So Sullivan and the FBI focus on where in the US the two could be. They believe Bulger and Greig are in a warm climate near the ocean, a place where retirees are in abundance and they would blend in with everyone else. That still leaves the net much too wide.
Florida, Texas, South Carolina, and California are just a few states that fit the bill. Just as Sullivan begins to zero in on the fugitives, Bulger is about to go underground for good. Bulger has been on the FBI’s Most Wanted list for twelve years, the same time as the man who topped it, Osama bin Laden. Then on May 2, 2011, the world awakes to stunning news.
After a firefight, American forces kill Osama bin Laden and take custody of his body. While Americans celebrate the death of the al-Qaeda mastermind, eighty-one-year-old Whitey Bulger knows his days are now numbered. Whitey becomes number one on the FBI’s Ten Most Wanted list. That’s not good news.
The former crime boss knows the spotlight will now be on him, and he takes extra steps to protect himself. For the first time, neighbors notice a new sign on their apartment door: “Please do not disturb. ” He was hunkering down to provide cover. His girlfriend Greig also spreads a lie that her husband is sick.
She started telling neighbors who asked, “Where’s Charlie? ” and led on as if he had a little bit of Alzheimer’s. Hidden in his own apartment, the chances of anyone spotting Bulger now are almost zero. But back in Boston, Sullivan and his task force come up with a brilliant strategy to flush him out.
They release a public service announcement for a wanted criminal, with the key difference being, instead of doing the same old on Whitey, let’s focus on Catherine. The FBI offers a hundred thousand dollars for tips leading to Catherine Greig’s whereabouts. The photos are from the early 1990s. Sullivan figures that sixty-year-old Greig is more likely to be seen in public than Bulger.
She was known to be more social and out and about. She would be the one out getting groceries and doing daily errands. In terms of size alone, two states are key to producing strong leads. Sullivan wanted publicity in New York and Los Angeles, cities that would fit perfectly with the theory of an area where Bulger could be.
But his budget has been cut to the bone. They would have spent an enormous amount of the fifty thousand dollars on two cities. So New York and LA are left out. But Sullivan finds another way of reaching them: daytime TV.
Several daytime talk shows profile photos of Cathy Greig. The new public service announcement is screened across America. The ad goes out, and the calls start to flood in. Analysts work with Sullivan, answering phone calls and organizing the tips.
There’s no time to follow every lead, so he prioritizes, putting tips into low, medium, and high priority piles. By the second day of the PSA broadcast, the team determines that the highest number of calls all come from one place: Biloxi, Mississippi. Seven tips in a very short period of time all place Bulger in Biloxi. That obviously grabs their attention.
On the Gulf Coast, Biloxi is warm and on the water, fitting Sullivan’s profile. He sends local agents to check the sightings. Every single piece of information received in Biloxi is investigated. By now, it’s likely Bulger and Greig have seen the ad, giving them a forty-eight-hour head start.
Sullivan firmly believes that if they don’t capture him in the first couple of days, the campaign will not work. As the clock runs down, he is staring defeat in the face. But what he doesn’t yet know is that the PSA has been picked up by international news channels and is being shown across the globe. On the second night of its release, it airs in Iceland.
One woman can’t believe what she is seeing. She’s sitting at home in Reykjavik, watching the publicity campaign, and she immediately recognizes the couple as her former neighbors. She knows instantly that it’s them. Day three, Sullivan comes in in the morning and there is a large pile of tips from the night before.
He goes through them and sees the Iceland tip. He immediately picks up the phone. The woman says she lives in Santa Monica, California for a few months every year. She tells Sullivan she is convinced the couple in the ad had been her neighbors in her apartment complex near the ocean.
They went by the name of Charlie and Carol Gasko. She and Cathy developed a bond through a cat. They struck up a conversation and became friendly, so she knew her. Something else stuck in her mind: Bulger’s temper.
They got into a little fight one time, and she saw that streak of the Whitey everyone knows, the vicious, nasty Whitey. That explosion of anger in a normally meek old man had stayed with her. Everything seemed to sound exactly like the way they would picture Bulger and Greig living their lives. Sullivan hangs up hoping this tip is the real deal.
He scans government databases to see what they have on the Gaskos. They are able to confirm that a Charlie and Carol Gasko were living at that address in Santa Monica. But key information is missing. There are no identifiers or date of birth, no credit history.
Whoever was there was living under the radar. Next, he checks the Gaskos’ state IDs and driving licenses. There isn’t a single hit for either of them. That raises a lot of red flags that this couple was trying to go undetected.
Sullivan knows he hasn’t a moment to lose. He contacts the LA office immediately and advises them that this tip needs to be covered immediately, that he really feels there’s a possibility this could be them. The FBI dispatches agent Scott Garriola to follow up the lead. He arrives at the apartment complex and speaks with the apartment manager.
Garriola shows him photos of Bulger and Kathy Greig and asks, “Do you recognize these people? ” The manager says, “Yeah, those are my neighbors. ” They ask how sure he is, and he says one hundred percent. When the agent explains who Charlie Gasko really is, the manager is stunned.
They talk about raiding the apartment, barging in, but they’re reluctant because they’re not one hundred percent sure Whitey is home at the moment. They have to come up with gimmicks and ideas to lure him out. Garriola asks for the manager’s help in taking Bulger down. The manager has been running the apartments for five years and has just learned the man down the hall is cold-blooded killer Whitey Bulger.
He’s not too excited about knocking on his door, especially now that he knows who he is. Instead, he comes up with another idea. Down in the garage, each apartment has its own storage locker. He offers to call the Gaskos and tell them there’s been a break-in, knowing Whitey would certainly want to come down and check it out.
Garriola agrees, and the phone call is made. But no one answers. There’s real anxiety. They wonder if the couple has seen them.
It’s the FBI’s worst nightmare. Spooked by the act, Bulger and Greig have the jump on them yet again. Then suddenly, the manager’s phone rings. It’s Catherine Greig calling Josh, the manager, asking, “Josh, did you just call the apartment?
” Yes, he says, “Your storage locker has been broken into. I was thinking of calling police. ” And that’s when they can hear Whitey in the background saying, “Tell Josh I’ll meet him there. ” Garriola calls in his backup, and they race to establish a takedown position.
They hustle over to the basement garage. Bulger is alone. But if he’s armed, the agents know he won’t think twice about firing. There’s a sense of anxiousness when you know you’re about to make a capture, wanting to do it safely.
Lots of things go through your mind. Whitey rides the elevator down. The agents shout at him to freeze, to put his hands up, to get down on the ground. They’re yelling at him to get down on his knees.
And here he is, this old man in his early eighties. He looks down at a puddle on the floor and says, “No, I’m going to take a step. ” They’re yelling at him, “Don’t. ” He says, “I’m going to take a step to my right.
” And he did that. They moved in on him. They handcuffed him. It was over.
After sixteen years on the run, James Whitey Bulger is finally in handcuffs. Back in the apartment, girlfriend Kathy Greig is also arrested. As the agents examine the couple’s home, they make a chilling discovery. Little old Charlie Gasko had eight hundred thousand dollars in cash stuffed in the holes in the wall of the apartment and something like thirty guns, which he had collected while on the run.
He was ready for a war, although it didn’t come to that. Back in Boston, Sullivan gets the call he’s been hoping to hear for six long months. He has a little celebration in his kitchen, relieved that it’s finally over. Then the news breaks across America: fugitive Boston crime boss James Whitey Bulger has been arrested after spending sixteen years on the run.
Bulger returns to Boston to be tried. He denies he was ever an FBI informant and that he murdered women. But he is found guilty of thirty-one of the thirty-two charges against him, including involvement in eleven murders. For the alleged murder of Flemmi’s girlfriend, the court returns a verdict of no finding.
His conviction is a moment savored by the families of his victims who thought this day would never come, including the family of murdered truck driver Michael Donahue. They think he should sit in jail and rot and be miserable just like they have been for the last thirty years. Though it was the US Marshals and the FBI who finally took Whitey Bulger down, Sullivan knows it would never have been possible without the incredible dedication of Tom Foley and the Massachusetts State Police. They deserve all the credit in the world.
That is the group that was able to finally build a case against him and set in motion a sequence of events that first sent him on the run but eventually led to his capture and convictions. For Foley, the case was something that had hung over his investigative team for a long time. There were a lot of families out there involved in these investigations that Bulger had ruined.
Now, at last, he is paying for some of the things he did.
