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. Flemmi had gotten Di Silva a job as a barmaid at Blackfriars, a bar in the city’s financial district that was “mobbed up.” Di Silva was scheduled to work that night, but Flemmi called her and said, “Don’t go. Not tonight.” Di Silva stayed home. At Blackfriars that night, there was a slaughter. 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 Costa Rica and Florida, she never stopped worrying about 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, who Di Silva knew, and Deborah Hussey were “sickening,” but equally disturbing was the revelation that Flemmi began a sexual relationship with the fourteen-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 thirty-six years, with sixteen 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 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.”
In the twelve months since notorious mobster James “Whitey” Bulger was captured, he has been revealed to have feet of clay. Stripped of his power, with few cards to play, Bulger awaits some form of justice, be it death from old age (he’s eighty-two), or adjudication in federal court, where he stands accused of nineteen murders. Either way, Bulger will be made to pay, though, increasingly, it has become apparent that the many people and institutions of government that made Bulger possible will not be held accountable. One of the most violent and pernicious criminal conspiracies in the history of America is over, but for those who hoped that the prosecution of Bulger would be some form of final exposé on the Bulger era, the trial is shaping up to be a whitewash.
Having lived sixteen years on the run, twelve of those in an apartment near the beach in Santa Monica, California, with $822,198 cash and an arsenal of weapons stashed in a wall, Bulger was finally pinched after a tipster contacted the FBI with information about his fugitive girlfriend, Catherine Greig. Bulger and Greig, age sixty-one, were arrested on June 23, 2011 and returned to Boston, where Whitey had for nearly a quarter century maintained a criminal business that included extortion, loan sharking, narcotics, fraud, illegal gambling, and murder.
Last week, Catherine Greig received an eight-year prison sentence and $150,000 fine for aiding and abetting a federal fugitive. With time served and allowable reductions for “good behavior,” she is likely to serve seventy-six months. Bulger’s trial is scheduled to begin on November 5.
The evidence against Whitey is formidable. Since he went on the run in January 1995, most of his closest associates have cut deals with the government and testified at various hearings and trials, and they are likely to testify against Whitey at his trial. Any attempt to prosecute Bulger, however, is complicated by the fact that at the same time he was committing most of the alleged murders, he and his gangster partner, Steve Flemmi, were also working as top informants for the FBI.
It is Bulger’s role as a government informant, and how that role was fostered, facilitated, and kept confidential by a vast array of public servants, that has led many to suspect that the true nature of Bulger’s criminal career will never be fully explored in a court of law. Actions taken since Whitey’s arrest one year ago underscore these claims.
“The prosecution of Bulger is being carefully orchestrated,” says Harvey Silverglate, a renowned Boston criminal defense attorney and author who has written about the case. Silverglate uses the word
cover-up
to describe the prosecution’s motives, adding, “If they wanted to convict Bulger swiftly, they could have tried him in California on gun possession charges. Would have been an open-and-shut case. He’d have received a thirty-year sentence. Or in Oklahoma, where one of the murders occurred, they have the death penalty. But the U.S. Attorney’s Office in Boston is not about to let this case out from under its control. Because then details might come out that show a pattern of secrecy and cover-up going back generations.”
The cover-up kicked into gear last July when the U.S. Attorney’s Office announced they had dropped all counts in the indictment except for the murder charges. “It is in the public interest to protect public resources—both executive and judicial—by bringing the defendant to trial on the government’s strongest case,” said U.S. Attorney Carmen Ortiz. Dropping the racketeering counts had another benefit: It greatly diminished the possibility that Bulger’s trial would explore how his racketeering career was underwritten, in large part, by the U.S. Department of Justice.
One person who concurs with the cover-up theory is John Connolly, the former FBI man who was Bulger’s case agent in the years that he was an informant. Since 2002, Connolly has been in prison on numerous charges stemming from his relationship with Bulger and Flemmi, including a second-degree murder conviction. “The Justice Department is going to do everything within its power to try to make sure the full story never comes out,” says Connolly, via phone from a correctional facility in Chipley, Florida, where he is currently serving a forty-year sentence. Since Bulger’s apprehension, Connolly has not granted any public interviews—until now.
Born and raised in the insular blue-collar neighborhood of South Boston (Southie), Connelly knew Bulger from childhood. He was even closer friends with William “Billy” Bulger, Whitey’s younger brother, who would rise through the ranks of state politics to become president of the state senate and, arguably, the most powerful politician in the Massachusetts state legislature.
In 2008, after a two-month trial in Miami, Connolly was convicted of having fed information to Bulger’s crew that led to the murder of John Callahan, a crooked business partner of Bulger’s who the mobster was concerned might cooperate with a criminal investigation. Callahan was shot in the head by a Bulger associate, his dead body left in the trunk of a Cadillac near Miami International Airport. Before being convicted for his involvement in the Callahan murder, Connolly was sentenced to ten years on a federal conviction in Massachusetts for accepting gratuities, falsifying evidence, and obstruction of justice, including the charge that he tipped off Whitey about his imminent arrest back in late-1994, making it possible for Bulger to run.
Says Connelly, “[The Justice Department] put a hit out on me back in 2000. They decided I would be targeted to take the fall for this whole arrangement. And they’ve stuck to it ever since.”
Connolly hopes that the apprehension of Bulger will lead not only to his murder conviction being overturned, but also to his public exoneration. “My lawyers have information that since Bulger was brought in, he spoke to FBI agents and told them I had nothing to do with tipping him off [about a pending federal indictment]. And he told them I had nothing to do with this murder in Florida, not one damn thing.”
From 1975, when Connelly first enlisted Bulger as a Top Echelon informant, until 1990, when Connelly retired from the FBI, Bulger and the agent met often, shared meals, and traded information. Connolly acknowledges that Bulger was involved in criminal activity, but, he says, “I didn’t ask about that. My role was to protect Bulger and Flemmi so we could make cases against criminals based on information they gave us. That was my job. Everyone knew that they were top criminals and murderers.”
Though he insists there was nothing criminal in his relationship with Bulger, Connolly acknowledges there was a natural affinity between him and the Bulger brothers based on their shared Southie upbringing. In fact, in the early-1990s, following his retirement, Connolly says he’d heard that criminal investigations of “Jimmy” (Bulger’s friends never called him Whitey) were under way. He had a friendly conversation with Senator Billy Bulger, saying, “You know, I hear your brother is involved in things that could get him into big trouble. You should tell him maybe it’s time to change his lifestyle and retire to Florida.” Says Connolly, “Billy sighed, looked at me, and asked, ‘John, you ever try to tell an older brother what to do?’ I knew what he meant.”
The crucial question about Bulger’s trial is whether or not the evidence might reveal that Connolly was merely a foot soldier in a much larger campaign of secrecy and corruption that spanned generations. The forces that sustained Bulger involved not only the entire Boston office and regional supervisors of the FBI, but stretched into the U.S. Attorney’s Office and possibly involved federal judges.
Federal prosecutors are on a track to make sure this version of the Bulger narrative does not surface at his upcoming trial. “The DOJ has no appetite for any kind of self-examination,” says Thomas Foley, a former colonel with the Massachusetts State Police who spent the better part of his career in law enforcement trying to take Bulger down. “To air all this out now would give a lot of people a black eye. They just want it all to go away.”
The roots of Bulger’s “special relationship” with law enforcement goes back before Bulger was a big player in the city’s underworld. In the early hours of March 12, 1965, in a dark back alley in Boston, a low-level hood named Teddy Deegan was filled with lead and left for dead. Deegan had fallen afoul of a psychotic Mafia-connected hit man named Joe “the Animal” Barboza. It was Barboza who murdered Deegan after asking for permission from Raymond Patriarca, boss of the Patriarca crime family, which then controlled New England. Barboza was assisted in murdering Deegan by another gangster named Vincent “Jimmy the Bear” Flemmi, brother of Steve Flemmi, who would one day be Bulger’s partner in crime. The murder of a small timer like Deegan would normally have been a minor event. But the government had a problem. The killers, Barboza and Flemmi, were both Top Echelon informants for the FBI.
The feds knew that these two men murdered Deegan. In fact, the FBI had bugged Raymond Patriarca’s home in Providence, Rhode Island, and captured on tape the conversation where Barboza asked for and received permission to whack Deegan. But the FBI did not want to lose their highly prized Top Echelon informants. What they did next would alter the trajectory of criminal justice in the region for a generation. The FBI and prosecutors had Barboza take the stand and tell a fabricated version of the murder that would lead to the conviction of two innocent men, Peter Limone and Joe Salvati. After being declared guilty, Limone and Salvati were sentenced to death row.
The framing of innocent citizens in a capital murder case by withholding evidence and suborning perjury—all to protect notorious criminals who were government informants—became the dirty secret of federal law enforcement in New England. In the years that followed, the convictions of Limone and Salvati would be challenged in various local jurisdictions but the government always fought back. It is difficult to know how many agents, assistant U.S. attorneys, district attorneys, and cops were in on the conspiracy. Prosecutors understood that they were to do everything within their power to preserve the convictions and ensure that no further examinations of the evidence would ever take place in court. Virtually the entire system became part of an effort to safeguard the false conviction so that criminals, protected by the government, could remain free.