The dirt floor in the cellar at 799 East 3rd Street in South Boston was cold that night in November of 1985. 26-year-old Debra Hussey didn’t know she was walking into her own grave. She walked through the front door expecting her stepfather. She walked into a trap. Within minutes, James Whitey Bulger had a rope around her neck, and Stephen Flemmi, the man who raised her, the man who had been sleeping with her since she was a teenager, stood there and watched her die.
Then he pulled her teeth out with pliers. Then he buried her in the ground beneath the house. She’d been wearing a sweater her mother bought her. She was the third body to go into that cellar. This wasn’t a hit. This wasn’t business. This was a man murdering his own stepdaughter because she’d become inconvenient.
Stephen “The Rifleman” Flemmi was a top-echelon FBI informant, a Winter Hill Gang enforcer, a man who had killed dozens, and Debra Hussey was the secret he couldn’t let walk around Boston anymore. She knew too much. She talked too much. She was using drugs, and she was angry, and she was telling people what he’d done to her.
So, he made a phone call to Whitey, and Whitey said, “Bring her over.” This is the story Hollywood left out of Black Mass, the chapter Johnny Depp never filmed. This is how an FBI-protected gangster murdered the little girl he’d helped raise, how her body sat in a Boston cellar for 15 years while her mother filed missing person reports, and how Stephen Flemmi sits alive today in federal protective custody after he should have been executed by the state of Oklahoma.
This is the darkest corner of the Bulger story, and it starts with a child who never had a chance. You have to understand who Debra Hussey was before you understand what they did to her. She was born in 1959 in Boston. Her mother was Marion Hussey, a working-class woman from the neighborhood who got involved with Stephen Flemmi when Deborah was around 2 years old. Flemmi was already married.
Flemmi was already a killer. By 1965, he was on the run for a car bombing that nearly killed a lawyer named John Fitzgerald. He fled to New York. He came back in 1974 when the charges fell apart. And when he came back, he moved in with Marion Hussey and her kids. Deborah was a teenager by then.
And that’s when, according to her own testimony years later in federal court, Stephen Flemmi started having sex with his stepdaughter. She was 15 years old. Maybe 14. The exact age was disputed in court. What wasn’t disputed was that it happened. Flemmi admitted it on the witness stand. He admitted it like he was reading a grocery list.
He’d raised her since she was a toddler. He’d taken her to school. He’d put her in his car and driven her around like a daughter. And then he started sleeping with her. And he kept sleeping with her into her 20s. Deborah grew up broken. She started using drugs, heroin, cocaine. She worked as a prostitute in the combat zone, Boston’s old red-light district downtown.
She bounced in and out of trouble. By the early ’80s, she was in her 20s, strung out, furious, and she had a mouth on her. She’d tell anyone who’d listen what Stephen Flemmi had done to her. She’d show up at his businesses high and screaming. She’d call her mother and threaten to blow everything up. She became, in the cold language of the Winter Hill gang, a problem that needed solving.
And here’s where you have to know who was solving the problem. Stephen Flemmi was 61 in 1985, a wiry, intense, dark-eyed gangster from Roxbury. He’d been a paratrooper in Korea. He’d been a made associate of the New England Mafia and a top lieutenant in the Winter Hill gang. Most importantly, he’d been a paid FBI informant since the ’60s.
His handler was a Boston Irish kid turned agent named John Connolly. And Connolly’s other prize informant was Flemy’s partner, a South Boston gangster named James Joseph Bulger. Everyone called him Whitey. Bulger was 56, white hair, ice-blue eyes, gym body, vegan diet. He didn’t drink, he didn’t smoke, he read history books, he ran South Boston like a feudal lord.
And he and Flemy had a deal with the FBI that was the dirtiest secret in American law enforcement. They informed on the Italian Mafia. In exchange, the FBI protected them, tipped them about wiretaps, tipped them about witnesses, tipped them about indictments. The agents who were supposed to police them became their partners.
By 1985, Bulger and Flemy had been killing people in basements for years. The house at 799 East 3rd Street belonged to a Bulger associate named Patrick Nee for part of that time, though the ownership changed hands. It was a quiet two-story home in the Telegraph Hill section of Southie. Nothing fancy, nothing memorable, but it had a dirt floor cellar.
And a dirt floor cellar is the only thing a Boston gangster needs to make a person disappear forever. Two bodies were already down there. Arthur “Bucky” Barrett, a safe cracker they’d robbed and tortured for his money in 1983. John McIntyre, a fisherman they’d suspected of cooperating with the Feds in 1984.
Both strangled, both shot in the head for insurance. Both stripped of their teeth so dental records couldn’t identify them if the bodies were ever found. Both lying in shallow graves in the same cold dirt where Deborah Hussey was about to join them. The decision to kill her wasn’t dramatic. According to Flemmi’s later testimony, and according to Kevin Weeks, the Bulger lieutenant who would eventually break and tell the whole story, it was a conversation between two old partners.
Flemmi told Bulger that Deborah was out of control. She was using. She was talking. She was threatening to go to the police about what he’d done to her as a girl. She was a liability. Whitey listened. Whitey nodded. Whitey said the words that ended her life. “Bring her by the house.” She came willingly.
That’s the thing that haunts the case. She came willingly because Stephen Flemmi was her stepfather, and she trusted him in some broken way, even after everything. The exact date is recorded in the federal indictments as on or about a day in 1985, but the men who were there have said it was late in the year, the cold months. She walked through the door.
Bulger was waiting. The accounts that emerged in court, primarily from Kevin Weeks and from Flemmi himself once he flipped, describe what happened next in a way that no Hollywood film has ever dared to show. Bulger grabbed her from behind. He put a rope around her neck. He pulled. He was a strong man, and she He was a slight woman, and it didn’t take long.
She struggled. She kicked. She made the sounds people make when they understand in the last seconds what is happening to them. And Stephen Flemmi, the man who’d raised her since she was two, stood and watched until she stopped moving. Then, according to his own testimony, he leaned over the body of his stepdaughter, and he checked to make sure she was dead.
What happened next was the Winter Hill gang’s standard procedure for disappearing a person. They stripped her body. They pulled her teeth out one by one with a pair of pliers because teeth carried dental records and dental records identify the dead. Flemy did the teeth. He admitted it on the stand. The man who’d taken her to school pulled her molars out of her jaw with hardware store pliers so that nobody would ever know it was her if the body turned up.
Then they wrapped what was left of Debra Hussey and they carried her down into the dirt cellar. They dug a hole. They put her in. They covered her over and they went upstairs and they had coffee. That’s how Kevin Weeks described it later. They had coffee. Now here’s what you have to understand about the next 15 years.
Marion Hussey, Debra’s mother, the woman who had loved Stephen Flemy and trusted him with her children, didn’t know her daughter was dead. She knew Debra was missing but she didn’t know. And Flemy let her not know. He sat with her. He held her hand. He told her Debra had probably run off, probably gone south, probably gotten into trouble somewhere.
He looked into her eyes and he lied to her face for 15 years while her daughter rotted under the dirt of a house 3 miles away. For the rest of the ’80s and into the ’90s, Bulger and Flemy kept running South Boston. They kept informing for the FBI. They kept killing people the FBI looked the other way on. John Connolly kept tipping them.
By 1995, the deal was finally cracking. A new federal prosecutor named Fred Wyshak was building a case. The Drug Enforcement Administration and the state police, who hated the FBI by then, were closing in. Indictments were coming. And in January of 1995, John Connolly tipped off Whitey Bulger one last time. Bulger ran.
He vanished into a 16-year fugitive run that would end in a Santa Monica apartment in 2011. Flemy didn’t run. Flemy thought his FBI protection would hold. He was wrong. He was arrested in January of 1995 outside a Boston restaurant called Schooners. And once he was in custody, the dam started to break.
Kevin Weeks, the Bulger lieutenant, the kid from the project who’d carried bodies and stood lookout, got indicted in 1999. Weeks did the math. He looked at the federal time he was facing. He looked at the loyalty Whitey had shown by running and leaving everyone behind. And Kevin Weeks did what no Southie kid was ever supposed to do. He cooperated.
Weeks took the FBI and the state police to the house at 799 East 3rd Street in January of 2000. He told them what was buried in the cellar. He told them where. The FBI agents and Massachusetts state troopers and forensic anthropologists went to that quiet little house in Telegraph Hill and they dug.
The dirt floor gave up its dead. Three bodies. Bucky Barrett, John McIntyre, and the small skeletal remains of a young woman with her teeth pulled out. Dental records were useless. They identified Deborah Hussey by DNA, by her mother’s DNA. By the cells Marion Hussey carried that she’d given her daughter 26 years before her daughter was strangled in a basement 3 miles from her home.
Two more bodies turned up at a separate site that same season. Five total Winter Hill victims pulled out of the Boston ground in less than a year. The case exploded. Whitey was on the lam and on the FBI’s 10 most wanted list sharing space with Osama bin Laden. Flemy was facing the death penalty. That’s the part most people don’t know.
Stephen Fleming could have been executed, not by Massachusetts. Massachusetts didn’t have the death penalty, but the killing spanned states. Fleming and Bulger had murdered a man named Roger Wheeler in Tulsa, Oklahoma in 1981. Wheeler owned World Jai Alai, a gambling operation Bulger and Fleming were skimming from.
They had a hitman named John Martorano drive to Oklahoma and put a bullet through Wheeler’s face in a country club parking lot. Oklahoma had the death penalty. Oklahoma wanted Stephen Fleming. Florida wanted him, too. There was a Tulsa businessman’s lawyer named John Callahan whose body had been found in a car trunk at Miami International Airport in 1982.
Same crew. Florida had the death penalty, and federal prosecutors in 2003 were preparing to charge Fleming with capital murder in jurisdictions that would put him in a death chamber. So, Stephen Fleming made the only move left to make. In October of 2003, he cut a deal. He pleaded guilty to 10 murders. He agreed to testify against everyone, including John Connolly, the FBI agent, including Whitey Bulger himself, if they ever caught him.
In exchange, Oklahoma and Florida agreed not to pursue the death penalty. He got life. Life with no parole. Life in a secret federal facility. The witness security program inside the Bureau of Prisons. Protected, fed, alive. Deborah Hussey’s family sat in the courtroom in 2008 when Fleming finally took the stand at the trial of John Connolly. He admitted everything.
He admitted the abuse. He admitted he started having sex with her when she was a teenager. He admitted he stood there while Whitey strangled her. He admitted he pulled her teeth out himself. He said it flat. He said it without crying. The man was in his 70s by then, and he spoke about murdering his own stepdaughter the way a clerk reads a receipt.
Marion Hussey was in the gallery. She heard him. She’d loved him for 20 years. She finally understood what kind of thing she’d been sleeping next to. In 2011, the FBI finally found Whitey Bulger. He was 81 years old living under the name Charles Gasko in a rent-controlled apartment in Santa Monica, California with his long-time girlfriend Catherine Greig.
They found $822,000 in cash in the walls. They found 30 firearms. They flew him back to Boston in chains. His trial started in June of 2013. Stephen Flemmi was the star witness. Flemmi walked into that federal courtroom in South Boston, an old man in a sweater, and he sat across from his old partner of 30 years, and he told the jury everything.
He told them about Deborah Hussey. He told them how Whitey strangled her. The defense lawyer asked Flemmi if he’d had sex with his stepdaughter when she was a teenager. Flemmi said yes. The defense lawyer asked if he was the one who pulled out her teeth. Flemmi said yes. Whitey Bulger, sitting at the defense table, called Flemmi a liar under his breath, loud enough for the jury to hear.
The judge had to admonish him. The jury convicted Bulger of 11 of the 19 murders he was charged with. Deborah Hussey was one of the murders where the jury could not reach a unanimous verdict on Bulger’s direct participation. Flemmi was the only eyewitness, and Flemmi was a confessed killer and rapist trading testimony for his life.
So, on Deborah’s murder specifically, the jury wrote no finding. But Whitey got two consecutive life sentences plus five years. He was 83 years old. He was going to die in federal prison. And in October of 2018, he did. They transferred him to a penitentiary called Hazelton in West Virginia. Within 24 hours of arrival, three inmates with Mafia ties beat him to death in his cell with a padlock stuffed in a sock.
He was 89. He never saw it coming. The man who’d murdered for 50 years died exactly the way he’d lived. Stephen Flemmi is still alive. As of this recording, he is in his early 90s, held in protective custody in an undisclosed federal facility somewhere in the United States. He has access to a television. He has access to commissary.
He eats three meals a day paid for by the taxpayers of a country he spent his life robbing and killing in. Roger Wheeler’s family in Oklahoma will never see him executed. John Callahan’s family in Florida will never see him executed. Marion Hussey, who buried her daughter’s bones in 2000 after 15 years of not knowing, will die without ever seeing the man who killed her child face anything more than a cell.
That’s the real cost of the Bulger-Flemmi deal with the FBI. It wasn’t just that John Connolly went to prison, though he did. Convicted in Florida in 2008 of second-degree murder for tipping the gang that John Callahan was about to talk. It wasn’t just that the FBI’s Boston office was humiliated. The real cost was Debra Hussey and John McIntyre and Bucky Barrett and Debra Davis, Flemmi’s other girlfriend, who he also helped strangle in 1981 because she wanted to leave him.
The real cost was the people who died because two killers had federal badges protecting them. The house at 799 East 3rd Street still stands. People walk past it every day. Kids ride bikes on the sidewalk. The dirt floor in the cellar has been excavated and sealed. Someone lives there now. They probably don’t know.
Or maybe they do and they don’t think about it. Boston is a city built on graves. The Winter Hill gang just made a few of them themselves. Here’s what the Black Mass movie left out. Here’s what Hollywood couldn’t put on the screen. The Bulger story isn’t really about two Irish gangsters from Southie outsmarting the FBI.
It isn’t really about the corrupt agents or the rat informant or the brother who became Senate President. The Bulger story at its center is about a young woman named Deborah Hussey who was molested by her stepfather as a child, strangled by his best friend as an adult, and buried in a cellar by both of them while her mother lit candles in a church across town praying she was alive.
Everything else, every federal indictment, every wiretap, every chase scene through Santa Monica, every prison cell is just the noise around that one quiet terrible truth. Stephen Flemmi murdered his own stepdaughter. Whitey Bulger helped him do it. The FBI knew the kind of men they were protecting.
And Deborah Hussey, 26 years old, was buried in the dirt with no teeth in her mouth so nobody would ever know her name. She has a name now. Her name was Deborah. And as long as anyone tells this story, the man who killed her will never get to forget it. If this story moved you, hit subscribe. We drop a new mob documentary every week.
