Whitey Bulger’s Women: Inside the Terror and Glamor of His Ex-Girlfriends
Catherine Greig was sentenced to eight years in prison for helping fugitive Whitey Bulger on his 16-year run from the FBI. Greig becomes the latest girlfriend of the mob boss to suffer for her love. T.J. English exclusively speaks to “the other woman” in the Bulger saga, Teresa Stanley, and other mobster ex-girlfriends about the terror and glamor of their life.
When Catherine Greig, girlfriend and fugitive partner of gangster James “Whitey” Bulger, walks into federal district court in Boston this week, she will face her moment of reckoning. After 16 years on the lam with Bulger, most of those years spent living in an apartment in Santa Monica, Calif., under assumed names and false identities, Greig, age 60, pleaded guilty three months ago to charges of identity fraud and harboring a fugitive. She is expected to receive a sentence somewhere between three and five years. Having already served one year in prison, she could walk free in 33 months. Not bad, considering that some of the women who entered the realm of Bulger and his gangster partner, Steve Flemmi, were strangled to death and buried in a shallow grave.
When 26-year-old Debra Davis sought to end her relationship with Flemmi, she was lured to an apartment on Third Street in South Boston and strangled in the basement, allegedly by Bulger. Four years later a similar fate befell Deborah Hussey, also 26, Flemmi’s stepdaughter from a relationship with his common-law wife, Marion Hussey. When Deborah Hussey openly accused Flemmi of having sexually molested her as a teenager, she wound up allegedly garroted by Bulger, her teeth extracted, and her body dumped in a grave not far from Whitey’s condominium in Quincy, Mass.
The killings are disturbing enough, but for the women who circulated in the orbit of Bulger and Flemmi, there were other costs. Appearing in federal district court for her guilty plea, Greig seemed fragile and traumatized. Her voice rarely rose above a whisper. Asked by the judge if she had ever sought psychiatric counseling, Greig wept openly.
At least two other women who had relationships with Bulger and Flemmi can identify with the state of posttraumatic stress Greig might be experiencing. To them, her story is a cautionary tale. These women also could have wound up dead, or on the run with a murderous gangster and psychotic control freak, or in prison awaiting sentencing. Instead, they are alive and free, though, like Greig, they carry with them a lifetime’s worth of psychological baggage from their years of deceit and paranoia as the girlfriends of underworld criminals.
For nearly 20 years, Teresa Stanley has endured a checkered legacy as “the other woman” in the Whitey Bulger saga. Her feelings about this are mixed. On one hand, she regrets that she was ever any kind of woman to Bulger, a man who romanced, dominated, and then betrayed her. On the other hand, she resents being known as a second-class paramour when, in fact, she lived with Bulger for 30 years. If anything, Stanley believes it was Catherine Greig who was the other woman.
“It’s hard to live with,” says Stanley. “Not only did I share my life with a man who is now accused of these terrible things. But he deceived and betrayed me by having this other life with Catherine. He humiliated me in the eyes of the town.”
In the media, Stanley is often portrayed as Whitey’s attractive but dumb common-law wife. At age 70, her fresh, girl-next-door good looks have faded, but she is certainly not dumb. In two separate interview sessions, Stanley—who rarely talks to the media—was thoughtful and reflective, as she looked back over her 30-year relationship with a man whose criminal history, and upcoming trial, has riveted the city.
“To me, he was just Jimmy, the man I lived with,” she says. “I never thought of him the way other people do.”
Bulger and Stanley are both products of “Southie,” a close-knit, mostly Irish Catholic enclave nestled along the Boston waterfront at Castle Island. When Stanley first met Bulger, in 1966, she was a 26-year-old woman with four children. Bulger had recently returned to Boston from a stint in prison on armed-robbery charges. Stanley had no idea that he’d also once been charged with rape, in Montana, while serving in the Air Force in the 1950s. Bulger was not rich at the time or the mobster of legend that he would later become. To her, he was a strong male figure offering to play a significant and much-needed role in her life as a protector and father figure to her children.
“There was a strong physical attraction,” says Stanley. “He was very handsome. And he was classy, always looked sharp, everything in place. He liked quality. He used to brag about the value of things he owned, a watch or shoes or whatever. And he was smart. He could intimidate people with his intelligence. He used big words, spoke in complete sentences with proper grammar. You couldn’t win an argument with Jimmy; he was too smart. When I watched him with other people, he stood out. He was a leader. I thought, gosh, maybe some of that will rub off on me.”
Bulger told Stanley, “With me, you will never have to work a day in your life. I will take care of you. I will be a father to your children. I will provide for your every need.” In return, Bulger had Stanley learn to cook, “though I never really liked it.” He set her up in a home in Southie and made sure she kept it spotless. He turned her into the woman he wanted her to be.
Stanley knew her boyfriend was some type of criminal. Southie had a long tradition of gangsters and racketeers going back to the Prohibition era, when illegal booze was offloaded at Carson Beach. She believed he made his money from illegal gambling and maybe loansharking. She heard stories that he had killed people during the Boston gang wars of the early 1960s. This did not dissuade her.
“It could be exciting,” she admits. “You walk into a restaurant or neighborhood place, and everyone notices you. You get the best tables. People treat you like you are special. It’s very easy to be seduced by that.”
Given that Bulger was a professional criminal, there was a lot of secrecy in his life. Though he usually checked in with Teresa, he could be gone for days at a time. Stanley had no idea that, along with being a rising star in the city’s criminal underworld, Whitey and his partner Flemmi were both confidential informants for the FBI.
By the late 1970s, Bulger and Flemmi used their secret relationship with law-enforcement authorities as a way to eliminate underworld rivals and take over the rackets in Boston. They allegedly fed information to the FBI and U.S. Attorney’s Office, making it possible for prosecutors to take down the most powerful Mafia family in Boston. Bulger and Flemmi became gods of the underworld. Virtually any criminal operating in Boston or the New England area paid tribute to them.
Stanley knew little about this, mostly by choice. She avoided newspaper articles about Bulger, though sometimes neighborhood rumors were hard to ignore. In the late 1980s, when a cocaine operation in Southie was broken up, leading to many arrests and prosecutions, neighborhood people asked an obvious question: how could this level of criminal activity be taking place without Whitey knowing about it and getting a piece of the action? Whitey told Teresa, “You’ll hear rumors, but let me ask you: Have you ever seen me around drugs? Have you ever seen me spending time with the kind of people who use or deal drugs?”
Stanley chose to believe Whitey. Later, it would be revealed that Bulger—who often bragged that he was keeping cocaine, heroin, and other hard drugs out of Southie—was, in fact, receiving a cut of all major dope transactions in the area.
The money rolled in. Stanley remembers being given the opportunity to select diamond rings, necklaces, and other goodies from boxes of jewelry, likely the bounty from robberies. Whitey paid for the house, school for the kids, and all other bills. Every week she was given an envelope filled with $500 cash, her “table money” for personal use. Stanley and Bulger took trips to Europe and around the U.S., always staying at the best hotels.
But there were problems. “He could be a very difficult man,” she says of Bulger. He was a control freak with an unpredictable temper. In attempting to be a father to Stanley’s four children, he was a harsh disciplinarian. The kids were grounded for minor infractions and sometimes physically threatened. Bulger ran background checks on the families of people her daughters were dating. He clashed especially hard with Stanley’s oldest son, Billy, who both worshiped and despised Bulger.
Then there was Bulger’s temper. Stanley remembers one time when they were in a hotel elevator and she exchanged pleasantries about the weather with another passenger. When they arrived in the lobby, Bulger grabbed Teresa by the arm and looked at her with eyes that could kill. “Don’t you ever make eye contact with another man like that ever again.” Another time, when she mentioned she’d helped a friend move some boxes into a car and accepted a $20 payment, Bulger went ballistic, calling her “low class” and a “whore.” Says Stanley, “You never knew what was going to set him off. It was unpredictable. I was afraid to say anything that would get him going. So mostly I said nothing.”
Although Bulger never struck Stanley, he was physically menacing. He grabbed and pushed and threatened her. Stanley’s fear of Bulger was such that whenever she smoked a cigarette—which Bulger, a health nut, was adamantly opposed to—she would have to sneak it when he was wasn’t around.
By the early 1990s, Stanley began to crack under the years of control and psychological domination. She and Bulger were arguing constantly, sometimes violently, at home and in public. Once, at a wedding party, Teresa was approached by Bulger’s partner, Flemmi, who said, “Teresa, I know you and Jimmy are going through a rough patch, but there’s something you need to understand. That man will never let you go.”
Stanley felt trapped. She went into a deep depression. She had become financially and emotionally dependent on Bulger; she could see no way out. Then, the “other woman” entered the picture.
Stanley was home alone one night when she got a call. An unfamiliar female voice said, “I think we need to talk.”
Teresa agreed to meet the woman. At a designated location, they arrived by car. A window rolled down and Teresa saw Catherine Greig, whom she did not know. When Teresa sat in the passenger seat of Greig’s car, she asked, “What is this all about? Who are you?”
Catherine answered, “I’m Jimmy’s girlfriend.”
Teresa suspected there had been other women, floozies, she assumed, whom Bulger used for sex and then discarded. She asked Catherine, “For how long?” thinking the answer would be three or four months.
“Twenty years,” said Catherine.
Teresa felt as if she’d been kicked in the stomach. She and Catherine drove to the condominium in Quincy where Whitey had set up an entirely separate domestic life with Greig. There, Greig told her the entire story of her long relationship with Bulger. Says Stanley, “Here’s the man I have a life with. He’s been a father to my kids, walked my daughter down the aisle on her wedding day. I’ve devoted my whole life to him—and he has this entirely other life!”
As Stanley was absorbing this information, in walked Whitey, with his underling Kevin Weeks.
Bulger had no idea that Greig had contacted Stanley and deliberately blown his cover. When he saw the two women together, he exploded. Remembers Stanley, “He grabbed Catherine around the neck and started choking. ‘You bitch, what have you done?’ She shoved him back. He fell over the arm of the couch and grabbed the Venetian blinds, accidentally tearing them down.” Catherine pointed at Teresa and shouted at Jimmy, “I can’t believe you put this woman in the same ballpark as me!”
Now Teresa was irate. The same ballpark! “I lived with this man for 30 years, and here they are talking about me like I was nothing.”
Weeks, who had been at Bulger’s side during murders and the disposal of bodies, vividly remembers the incident. “It was wild. I thought Jimmy was gonna kill Catherine. I grabbed him to stop him from choking her. Teresa didn’t want to leave, but I grabbed her too and got her out of there.”
In the wake of this incident, Bulger supposedly ended the relationship with Greig. He said to Stanley, “I see I’ve been hard on you. Let’s go on a trip. Anywhere you want to go.”
In December 1994, Bulger and Stanley set out on a drive across the country. It was supposed to be a one-month trip all the way to California. As they drove through the Midwest, Stanley stared out the window at the passing scenery. She had fallen deeper into depression, feeling that she was hopelessly trapped in an abusive relationship.
When they pulled off the road and into a lodge for an overnight stay, Bulger could see that Teresa was upset. “Why the sourpuss?” She seethed and said, “Maybe it’s because I belong in some other ballpark.” Then she did something she’d never done in the 30 years her and Bulger were together. She pulled out a cigarette, lit it, and puffed away, right in front of Whitey. It was her way of saying, “This charade is over. I want to go home.”
On the drive back to Massachusetts, Stanley and Bulger heard over the car radio that Steve Flemmi had been arrested and Bulger was being sought by a federal task force. They detoured to New York City. From there, Bulger communicated with underlings back in Boston, determining that he would have to go on the lam. He asked Teresa to accompany him. “I knew it was a mistake. My mother told me not to do it. But where I come from, loyalty is an important value. I’d spent 30 years with this man. He needed me.”
Stanley said she would do it, but then the depression set in again. She had four children and a whole lifetime of relationships she would be leaving behind. She couldn’t do it. She told Whitey she wanted to go home.
Under cover of darkness, they drove back toward Boston. Late one night, Stanley was dropped off at her daughter’s house in Hingham. She never saw Bulger again. He drove immediately to Malibu Beach, in Dorchester, where he’d made arrangements to pick up Greig.
Teresa Stanley’s 30-year personal relationship with Whitey Bulger was over, but the repercussions of that relationship continued. With Bulger on the FBI’s 10-most-wanted List right behind Osama bin Laden, Stanley was hounded by the FBI. She and her family were under constant surveillance. As details about her former boyfriend’s criminal life exploded into the public domain through sensational revelations in court, her feelings of betrayal deepened. Eventually, she cooperated with investigators by giving them information about one of Bulger’s aliases, Thomas Baxter, which led them to seize a bank account in Tampa, one of many Bulger had opened around the country to facilitate his life on the run.
Stanley is still in a state of shock from the legacy of deception and depravity left by Bulger. Learning that he and Flemmi are alleged to have murdered women with their own hands, she says, “It’s horrible. You ask yourself, what kind of people are these? And why didn’t I see it or recognize it?”
Mostly, Stanley tries to stay out of the media glare. She works as a waitress at the Boston Convention and Exhibition Center and rarely talks to reporters. Recently she was offered $10,000 to do an on-camera interview for the cable-television program I Married a Mobster. She turned it down. She was relieved to learn that her name is not on the list of potential witnesses to be called by the government to testify at Bulger’s trial, scheduled for Nov. 5. Even so, there is no escaping the consequences of her years with Whitey. “It never ends,” she says.
Back in the mid-1970s, Marilyn Di Silva, 64, also found herself slipping deeper and deeper into the seductive parallel universe of the Winter Hill Mob, as Bulger and Flemmi’s criminal crew was known to law enforcement. At age 26, a divorced mother with three young daughters, she landed a much-needed waitressing job at Chandler’s, a bar in Boston’s South End that was, unbeknownst to Di Silva, partly owned by mob boss Howie Winter. The bar was a gathering place for gamblers, mobsters, mafiosi, and, occasionally, corrupt cops and agents.
At Chandler’s, Di Silva met Stevie Flemmi, who was 15 years her senior. He was handsome, flirty, and always had a wad of cash from which he dispensed $10 and $20 bills. Di Silva knew that Flemmi had an estranged wife and a live-in girlfriend named Marion Hussey, but that was OK with her. “I had three daughters who I went home to every night,” says Di Silva. “I wasn’t really looking for anything permanent. I was a better prospect as a mistress than as a wife.”
The relationship with Flemmi was based mostly on sex and good times. Unlike Teresa Stanley, who was sweet and pliable with her gangster boyfriend, Di Silva was spunky and had a sharp tongue, which Flemmi found amusing. She learned early on that her new sugar daddy was a criminal of some type. Flemmi had recently returned to Boston after several years on the lam; he’d been ducking a murder charge that was eventually thrown out, likely with the help of the FBI. He didn’t hide his lifestyle. Within the first month they were together, Flemmi bought Di Silva a two-tone Cadillac and showered her with jewelry. “He was extravagant, very generous,” she remembers.
Flemmi set up Di Silva in an apartment next door to Marshall Motors, an auto garage in Somerville that served as the clubhouse of the Winter Hill Mob. “Because I was Italian, I was designated to cook lunch for them. In the apartment I’d make sandwiches, with cold cuts, or pasta. If I had my mother there, we’d make extra sauce, then walk it over to the garage.” Di Silva became the unofficial mascot for what would become the most notorious criminal gang in the city’s history.
As the daughter of a cop who grew up over a meat market in East Boston, Di Silva knew better than to ask a lot of questions. Clearly, the men who passed through Marshall Motors were not doctors and university professors. “I figured they were loansharks, leg breakers, bookies. Yeah, bookies. Money. That seemed to come up a lot.”
The garage is where Marilyn first met Whitey Bulger. “He was there almost every day,” she remembers. “Along with Stevie, Johnny Martorano, and sometimes Johnny’s brother, Jimmy. Whitey was always impeccable, with his jeans starched, the tight leather jacket. He was kind of a know-it-all, talked with a lot of authority on different subjects. Eventually, I could see that he was sort of taking over as the leader. He’d sit behind a big desk, his foot up, cleaning his nails with a knife he kept tucked in his boot.”
On numerous occasions, Di Silva hung out socially with Flemmi and Bulger together. “They took me to buy my first gun,” she remembers. Di Silva’s father had taught her how to shoot. “We went to this little shop, the three of us standing over the gun case. ‘That’s a nice one, I like that. The snub nose.’”
Occasionally they all went on double dates. Di Silva would set Whitey up with one of her friends. “One time, we were at Café Budapest. It was late. Whitey and his date, a friend of mine, were in another area. Suddenly, Stevie and I hear this bloodcurdling scream. We run over there. Whitey had pulled this big knife out of his boot, was flashing it around. It scared the hell out of my friend.”
Sometimes, Di Silva clashed with Bulger, who could be “uptight.” At the garage, after she cursed one time, Whitey said to Flemmi, ‘Listen to the mouth on that broad. She talks like a truck driver. Why you want a truck driver in your life?” Di Silva got right in Whitey’s face. “Fuck you,” she said. “This is the way I talk. You don’t like it, you can leave the room.” The others laughed. Bulger let it slide. At the time, Di Silva found the encounter comical, but looking back now, with what she knows about Bulger and Flemmi, she feels lucky to be alive.
It started to turn sour in 1978, after she and Stevie had been together four years. Flemmi had encouraged her to get a criminal-justice degree at a local community college. He wanted her to be a cop and even helped get her name on a five-year waiting list. Only the name on the list was not Marilyn Di Silva. Flemmi had created an entirely false identity for Di Silva, with a fake name, driver’s license, and birth certificate. Di Silva now believes that Flemmi and Bulger were angling to get her on the police force so she could serve as a mole for the Winter Hill Mob.
Di Silva now found herself being followed home by police cars and sometimes other unidentified vehicles. When her phone records were seized, she became worried. “God forbid, if something happened to me, who would take care of my girls? I asked Stevie, ‘What’s going on here?’ But he had a way of not answering questions. He told me not to worry.”
The last straw came on a night in 1978. Di Silva told Flemmi she was going that night to Blackfriars, a bar they sometimes frequented together, in the city’s financial district. “Don’t go,” said Flemmi. “Not tonight.” Di Silva stayed home. That night there was a slaughter at Blackfriars. The owner of the bar and two others were shot dead. Flemmi has denied any involvement in the Blackfriars shooting; it remains one of Boston’s most notorious unsolved crimes.
Di Silva’s dual life as a mother and a gangster’s girlfriend had lost its charm. She drove over to Marshall Motors one night and handed the keys to the Cadillac to Flemmi. “I can’t do this anymore,” she said. “I got my kids to worry about. It’s over for us.”
“Oh boy, if looks could kill, I think he could have killed me at that moment. He was, like, ‘What!? Nobody walks away from me.’” I think maybe the only reason I got away with that was because I had kids. I was a little older than his other girlfriends and had a life of my own. For whatever reason, I walked away from it. I was lucky.”
Though Di Silva moved out of the area, to Arizona and Belize and Florida, she never stopped worrying bout her past connections to Flemmi and Bulger, partly because she was frequently contacted by the FBI and other law-enforcement sources seeking details about her time with the gang. In the late 1990s, when Bulger went on the run and Flemmi turned stool pigeon, the lurid details started to come out.
“I was shocked,” says Di Silva. “I’m still shocked.” The grisly details of Flemmi and Bulger strangling Debbie Davis, whom Di Silva knew, and Deborah Hussey, were “sickening,” but equally disturbing was the revelation that Flemmi began a sexual relationship with the 14-year-old daughter of his common-law wife. “I remember him always asking me about my oldest daughter,” she says. “Did he have his eyes on her so he could move in when I got older? Was that his plan?”
Like Teresa Stanley, Di Silva is haunted by the knowledge that she could have circulated among men who were psychopathic killers and what that says about her. “You can’t take back the past,” she says. “It is what it is. But when I think back about it, it gives me the creeps.”
To some, Catherine Greig, like Teresa Stanley and Marilyn Di Silva, is guilty only of having made bad choices. She fell for a professional criminal and likely became enamored by the excitement and, most of all, the financial security it provided. She remained loyal to Bulger for 36 years, with 16 of those years under extreme pressure as co-fugitives from the law. Greig was either in love with Whitey, or living in fear, or under the throes of some manner of Stockholm syndrome.
Others see a more conniving co-conspirator. In the wake of Greig’s guilty plea, it was revealed in court that she was attempting to transfer co-ownership of her house and bank accounts into the name of her twin sister, Margaret McCusker. Rather than a woman in a state of trauma, claimed federal prosecutors, she was calculating ways to protect her property and bank accounts. U.S. district court Judge Douglas P. Woodlock has ordered that her assets be frozen until after she is sentenced.
One person who could feel vindictive toward Greig, but does not, is Teresa Stanley. “I have nothing to gain by Catherine doing a long time in prison,” she says. Stanley remembers a day last summer, after Bulger and Greig were apprehended, when she was approached by Catherine’s sister, who said, “Teresa, I’m sorry about what you’re having to go through,” adding, “You know, Whitey really loved you.”
“I thought about that,” says Stanley. “Did he love me? Really? How can you say that about a person who deceived you and lived a double life and shamed you in the eyes of everybody?”
Still, she does not blame the other woman. “All those years cooped up with Jimmy, traveling, living on the run, having to answer to his every command, that couldn’t have been easy.”