The REAL Frank Costello In The Departed Was Whitey Bulger – HT
October 6th, 2011, Plymouth County Correctional Facility, Massachusetts. 4:30 in the afternoon. James Joseph Bulier, 82 years old, sat across from his attorney in a windowless concrete room that smelled like bleach and stale coffee. 16 months earlier, he’d been pulled out of a rent controlled apartment in Santa Monica, California.
With $822,000 in cash stuffed inside the walls and 30 firearms hidden behind kitchen cabinets. He’d been a fugitive for 16 years. He’d been on the FBI’s 10 most wanted list, second only to Osama bin Laden. And now, in that concrete room, he leaned back and said one thing to his lawyer. I’m not a rat. Tell them I’m not a rat.
That was the only thing that mattered to him. Not the 19 murders, not the extortion, the racketeering, the cocaine. Just that one word, rat. This wasn’t just another mobster. James Whitey Bulier was the man who outsmarted the FBI for 25 years by becoming the FBI. He ran South Boston like a feudal lord while his brother William ran the Massachusetts State Senate.
He fed informants to law enforcement, then murdered the people they identified. He’s the only American gangster to ever convince an entire field office of the Federal Bureau of Investigation to work for him. And in 2006, when Martin Scorsesi needed a villain so dark, so manipulative, so paranoid that Jack Nicholson could chew the scenery for 2 and 1/2 hours, he didn’t invent Frank Costello.
He sanitized Whitey Bulier. This is the story of how a kid from a souy housing project became the most powerful organized crime figure in New England history. How he turned the FBI into his personal hit squad. And how Hollywood took his real life and made it gentler, kinder, more cinematic because the truth was too ugly to put on screen.
But here’s what the movie didn’t tell you. The most disturbing parallel between Frank Costello and Whitey Bulier isn’t the rats or the restaurant meetings or the cop on the payroll. It’s something Scorsesei cut out completely. And once you know what it is, you’ll never watch the departed the same way again.
James Joseph Bulier was born September 3rd, 1929 in Dorchester, Massachusetts, the second of six children. His father, James Senior, lost his arm in a railroad accident before Whitey was born. The family moved into the Old Harbor housing project in South Boston when Whitey was 8 years old.
Old Harbor was the first public housing development in New England. Brick row houses, clothes lines strung between windows. Irish Catholic families packed three generations to a unit. To outsiders, it looked like poverty. To the kids who grew up there, it was a kingdom with its own rules. Whitey was small for his age. Blonde hair so light it was almost white, which is where the nickname came from, though he hated it his whole life.
He preferred Jimmy. He was a reader. He kept canaries as pets. He had a lifelong obsession with cleanliness, washing his hands compulsively, refusing to eat food that touched. But by the time he was 13, he was running with a street gang called the Shamrocks, knocking over delivery trucks and rolling drunks coming out of the taverns on West Broadway.
His first arrest came at age 14. Lararseny, then assault, then armed robbery. By the time he was 20, Whitey had been arrested for forcible rape, but the charges were dropped when the witnesses suddenly forgot what they’d seen. That was the first sign of what made him different. Other Souy kids got caught.
Whitey made witnesses disappear without ever pulling a trigger. In 1956, at age 26, Whitey and three accompllices robbed three banks in Indiana, Rhode Island, and Massachusetts. They got away with $42,000. He was caught the next year hiding in a Rever Massachusetts nightclub with his girlfriend. The judge gave him 20 years.
And here’s where the story takes its first turn into the territory that Scorsesei never touched. Whitey Bulier did three years at the federal penitentiary in Atlanta. Then he was transferred to Alcatres, then to Levvenworth. While he was in Atlanta, he volunteered for what he was told was a medical study.
The doctors said it was research into a cure for schizophrenia. They paid the inmates $75 and offered time off their sentences. What it actually was was MK Ultra, Project MK Ultra, the CIA’s covert program to test mind control techniques on unwitting Americans. For 18 months between 1957 and 1959, Whitey Bulier was injected with massive doses of LSD.
He’d later tell his friends he was given the drug more than 50 times. He described nightmares so vivid he thought he was dying. He said he could hear the canaries from his childhood screaming inside the walls. He stopped sleeping. When he finally got out of prison in 1965, he was 35 years old, paranoid, insomniac, and convinced that the United States government had broken something inside his head that would never heal.
Most men come out of prison damaged. Whitey came out weaponized. He came home to South Boston and South Boston was at war. The Keen brothers, Donnie and Kenny, ran the Mullen gang’s main rival out of the Transit Cafe on West Broadway. They were old school Irish raketeers. Lone sharking, bookmaking, hijacking. Whitey went to work for them as muscle. He was patient.
He watched. He learned who paid, who didn’t, and who could be turned. In May of 1972, Donnie Colleen was shot to death in his own car outside his home in Framingham, Massachusetts. The Mullen gang took credit. Whitey went to the leadership of the Mullins and made a proposal. He wouldn’t avenge Donnie. He’d switch sides.
He’d help them finish off Kenny. And in exchange, when the dust settled, Whitey would run South Boston. Within 90 days, Kenny Colleen was sitting in a barber’s chair on West Broadway when a man walked in, put a 45 caliber pistol against the back of his head, and pulled the trigger. Witnesses saw nothing, heard nothing.
The killer walked out, got in a green Pontiac, and drove away. Whitey Bulier was now the boss of South Boston. He was 42 years old. Here’s what most people don’t understand about the Winter Hill Gang. And this is the kind of insider knowledge that changes how you see the whole story. The Winter Hill Gang wasn’t an Italian mob outfit.
It was an Irish-American syndicate based in Somerville, Massachusetts, founded by Howie Winter that absorbed the South Boston Cruise, the Charles Town Cruise, and a handful of Italian operators from Ravier. The Winter Hill gang ran the bookmaking, the lone sharking, the truck hijacking, and a horse race fixing operation that grossed over $8 million between 1973 and 1979.
The race fixing scheme worked like this. The opportunity east coast horse tracks from Suffach Downs in Boston to Pompo Park in Florida had small fields and underpaid jockeyies. The inside connection. The Winter Hill gang had a fixer named Tony Cula who could bribe a jockey for as little as $2,000. The execution Cula would pay four or five jockeyies in a single eight horse race to hold their mounts back.
The remaining horses, the ones Winter Hill bet on, ran clean. The money Winter Hill would spread their bets across multiple tracks and bookmakers to avoid suspicion. sometimes pulling down $400,000 on a single afternoon. The problem, Tony Chola got greedy, got caught, and in 1979, he turned federal witness.
21 members of the Winter Hill gang were indicted. But two of them, Whitey Bulier and his partner Steven the Rifleman Flemmy, were quietly removed from the indictment. That’s where everything changes. Steven Fleming was 44 years old in 1979. Born in Roxbury, Korean War paratrooper, two Bronze Stars, quiet, almost gentle in conversation.
He had two girlfriends in their early 20s named Deborah Davis and Deborah Hussie. He liked Italian cooking and gardening. He was also, by his own later admission, responsible for at least 10 murders. Fleming was the closest thing Whitey had to a brother. He was Whitey’s Mr. French, except Mr. French in the departed never sleeps with his stepdaughter and never strangles her in a basement. Flemmy did both.
The reason why Whitey and Flemmy escaped that 1979 indictment is the most consequential criminal alliance in American law enforcement history. In 1975, Whitey had been recruited as a top echelon informant by the Federal Bureau of Investigation. His handler was a Boston agent named John Connelly, a kid who’d grown up in the old harbor housing project.
two doors down from the Bulier family. Connelly was 34 years old, ambitious, well-dressed, and deeply convinced that taking down the Italian mafia, Lacosa Nostra, the patriarcha family of New England, was the most important work of his career. Whitey gave Connelly the patriarchas. He fed him names, addresses, meeting locations, internal disputes.
The FBI dismantled the New England mafia using information Whitey provided. And in exchange, the FBI protected Whitey. They tipped him off to wiretaps. They removed his name from indictments. They warned him when other agencies, the DEA, the Massachusetts State Police were closing in. They even on at least two occasions identified other criminals who were considering testifying against him.
And those people died. You have to understand what this means. It wasn’t a corrupt agent taking bribes. It was an entire FBI field office, including Conny’s supervisor, John Morris, who took at least $7,000 in cash and a case of expensive wine from Whitey, treating a serial killer as a protected asset for over 15 years. Connelly later wrote internal reports calling Whitey a strategic source.
He warned Whitey that a businessman named Roger Wheeler who owned World J Alli was going to expose Winterhill’s ski from the Florida operations. Whitey sent his hitman John Marterano to Tulsa, Oklahoma. On May 27th, 1981, Marterano shot Wheeler in the face in a country club parking lot. Wheeler had a wife and four children.
That was the pattern for the next decade. Whitey would learn through Connelly that someone was a problem. The problem would die. The FBI would close the case as unsolved. Now, think about the departed. Frank Costello has a cop inside the Massachusetts State Police, Colin Sullivan. Sullivan tips him off.
Sullivan kills the people who could expose Castello. The movie treats this as a clever plot device. The reality is worse. Whitey didn’t just have one cop. He had agents, supervisors, prosecutors. He had what the Department of Justice’s own internal review later called one of the worst betrayals of public trust in the history of American federal law enforcement.
By the mid 80s, Whitey had built a power structure that no one could touch. His older brother, William, called Billy, had risen from a Massachusetts state representative to president of the Massachusetts State Senate. Billy Bulier was between 1978 and 1996 the most powerful elected official in Massachusetts.
He controlled state budgets, judicial appointments, university presidencies. He was a fixture at parade reviewing stands and St. Patrick’s Day breakfasts. And while Billy was running the state house, his brother Jimmy was running everything else. drug shakedowns, lone sharking, bookmaking that pulled in $50,000 a week, extortion of every cocaine dealer south of the Charles River.
The headquarters was Triple O’s Lounge, West Broadway and F Street, South Boston, a two-story brick building with a green awning and no sign. Whitey didn’t drink. He’d order a glass of milk and sit at a back table watching the door. Inside Triple O’s, you could buy guns, sell coke, settle debts, plan murders.
The bartenders knew never to look at the back room. Triple O’s was Whitey’s Frank Castello restaurant. Except Whitey didn’t sit there to be seen. He sat there to see who came through the door. Whitey had rules. No one in his crew could be a heroin user. He despised heroin dealers, though he taxed every one of them.
He banned the word rat being said as a joke in his presence. He drilled his men in counter surveillance. He had them rotate through six different cars in a single afternoon. He insisted on meeting only on foot, walking along Castle Island, the South Boston Pier, where you could see anyone coming for half a mile in either direction.
He memorized the federal agents license plates. He kept binoculars in a leather case in his car. But it wasn’t paranoia if they were really after him. And by 1989, they were. A handful of investigators, mostly from the DEA and the Massachusetts State Police, had figured out what the FBI couldn’t see or wouldn’t admit.
They started building a parallel investigation. They couldn’t trust the Boston FBI office, so they kept their files in another state. In 1994, they had enough. A federal grand jury in Boston was about to return indictments against Whitey Bulier, Steven Fleming, and the rest of the Winter Hill Corps, charging racketeering, extortion, and money laundering.
On December 23rd, 1994, the day before the indictments were to be unsealed, John Connelly drove to a parking lot in Quincy, Massachusetts. He met with Whitey. He told him to run. Whitey already had cash hidden in safe deposit boxes in Dublin, Montreal, London, and Venezuela. He had multiple passports under multiple names, all real, all issued by the State Department to fake identities.
He had a girlfriend, Katherine Greg, a 43-year-old former dental hygienist who had agreed to disappear with him. Greg had no criminal record. She had two miniature poodles named Gigi and Nikki. She had a brother-in-law who was a Massachusetts state trooper. None of it mattered. She loved him. She left her life behind and walked away into nothing.
Whitey Bulier vanished on December 23rd, 1994. Steven Fleming was supposed to go with him. Fleming waited too long. He went to dinner with his girlfriend. He was arrested at a restaurant called Schooners in Boston on January 5th, 1995, 12 days later. Fleming never saw the outside of a prison again. Howie Winter was already in prison.
John Marterano fled to Florida. Frank CMI, the head of the New England mafia by then, was arrested in West Palm Beach. The whole Winter Hill structure collapsed. Whitey was 65 years old when he went on the run. He should have been a frail old man hiding in a basement. Instead, he and Katherine Greg moved through Louisiana, Wyoming, Mississippi, New York, and finally settled in 2007 in a rent controlled three- room apartment at 3003rd Street.
Apartment 303, Santa Monica, California. They paid in cash. They told the neighbors they were Charles and Carol Gasco, retirees from Chicago. Whitey grew a long white beard. He fed the alleycats. He gave money to the homeless. He bought a wide-brimmed hat and a new identity at every motel between Mississippi and California. 16 years passed.
Three Massachusetts FBI directors came and went. The Boston field office was completely restructured after the scandal broke. John Connelly was indicted, convicted of rakateeering, and later convicted of seconddegree murder for tipping Whitey off about John Callahan, a businessman who was killed in 1982.
Connelly is currently serving a 40-year sentence in Florida. In June of 2011, the FBI ran a new public service announcement campaign focused on Katherine Greg. They figured Whitey would be too disciplined to make a mistake. But Catherine, after 16 years in hiding, would still want to look like herself. The PSA showed photos of Katherine, described her vanity, her love of plastic surgery, her two poodles.
A former neighbor in Iceland who had visited Santa Monica that year recognized her face on television. She called the tip line. On June 22nd, 2011, FBI agents knocked on apartment 303. They told the man at the door they needed help. He came outside. They put him on the ground. 81 years old, he didn’t resist. They asked, “Are you James Bulier?” He said, “Yes, I am.
” Inside the apartment, they found $822,000 in cash, 30 firearms, and a list of names and addresses written in Whitey’s neat block handwriting. The list contained the home addresses of every person who had ever been believed to inform on him. He had been planning, even at 80, to come back and finish his work.
Whitey Bulier went to trial in Boston on June 12th, 2013. He was charged with 33 counts, including 19 murders. The trial lasted 8 weeks. The witnesses against him included John Marterano, who had murdered 20 people for the Winter Hill gang and gotten a 12-year sentence in exchange for testifying. Steven Fleming, who had been Whitey’s partner for 30 years, testified that Whitey had personally strangled Flemy’s stepdaughter, Deborah Hussie, in 1985 in the basement of a house on East Third Street, Souy, because Whitey thought she was talking too much. Flemmy
described how Whitey lay down on a mattress to rest after the killing, asking Flemmy to pull the teeth from Hussy’s mouth and remove her fingers so the body couldn’t be identified. The jury convicted Bulger on 31 of 33 counts, including 11 of the 19 murders. He was sentenced to two consecutive life terms plus 5 years.
The judge that day, Denise Casper, looked down from the bench at the 84year-old man in the orange jumpsuit and said, “The scope, callousness, and depravity of your crimes are almost unfathomable.” Whitey said nothing. He stared at the wall. On October 30th, 2018, James Whitey Bulier was transferred from a federal prison in Florida to United States Penitentiary Hazelton, a highsecurity facility in West Virginia.
He arrived in a wheelchair at 6:45 p.m. By 900 p.m., he was in his cell on the general population unit. At 6:00 a.m. the next morning, October 31st, Halloween, 2018, guards found him on the floor, his eyes gouged out, his tongue partly removed, beaten to death with a sock filled with padlocks. He was 89 years old.
The men suspected of killing him were mafia associates from Massachusetts. They never forgot what he was. Inside, in the only court that mattered to wise guys, Whitey Bulier was a rat, and rats die. Steven Flemmy is still alive, serving life in a federal prison in North Carolina, 89 years old as of last year. John Connelly is still in prison in Florida.
John Morano served 12 years and now lives quietly in Massachusetts. Katherine Greg served eight years for harboring a fugitive. She was released in 2020. Billy Bulier resigned as president of the University of Massachusetts in 2003 after refusing to fully cooperate with a congressional inquiry into his contact with his fugitive brother. He’s still alive.
What Whitey Bulier really teaches us isn’t a story about gangsters. It’s a story about institutions. The FBI didn’t fail to catch him. The FBI fed him. They handed him names. They cleared his way. He didn’t beat the system. He bought it for the price of information about people the system wanted gone more than it wanted him gone. That’s the real lesson.
And it’s the lesson Hollywood couldn’t quite tell. Now, think about the departed again. Frank Costello has the cop inside. Frank Costello obsesses about rats. Frank Costello meets at a restaurant. Frank Costello has the Steven Flemmy style enforcer. Scorsesei took all of those parallels straight from Whitey Bulier.
But here’s the parallel he left out. The brother in government. Scorsesei didn’t put Billy Bulier in The Departed. He couldn’t because the idea of one brother running the criminal underworld of an American city while his blood brother runs the elected government of that same state for 20 consecutive years untouched, unchallenged, unindicted, is too dark for a Hollywood film.
It’s the parallel that turns the departed from a crime story into something else. A story about how power, real power, doesn’t choose between the legal world and the illegal one. It uses both. But the most disturbing parallel, the one Scorsesei left out completely, isn’t even the brother. It’s something deeper.
Something about who Whitey was working for the whole time. We’ll show you tomorrow. If this story shook you, hit subscribe. We drop a new mob documentary every week on Mafia Talks. Drop a comment below. What do you think Scorsesei cut from the departed and