Whitey Bulger’s Trial Conspiracy: John Connolly Speaks

Whitey Bulger
From left: U.S. Marshals Service-AP; U.S. Attorney's Office-Boston Herald-Polaris (2)

In the 12 months since notorious mobster James “Whitey” Bulger was captured, he has been revealed to have feet of clay. Stripped of his power, Bulger awaits some form of justice, be it death from old age (he’s 82), or adjudication in federal court, where he stands accused of 19 murders. Either way Bulger will be made to pay, though it has become increasingly apparent that the many people and institutions of government that made Whitey Bulger possible will not be held accountable. One of the most violent and pernicious criminal conspiracies in the history of American mobsterism is over, but for those who hoped that the prosecution of Bulger would be some form of final exposé on the Bulger era, his trial is shaping up to be a whitewash.

Having lived 16 years on the run, 12 of those in an apartment near the beach in Santa Monica, Calif., 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 61, 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.

Earlier this month 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 76 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 the way 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 30-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 suspected 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, who declined to be interviewed. Dropping the racketeering counts would have had another benefit—greatly diminishing 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, Fla., where he is currently serving a 40-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), Connolly knew Bulger from childhood. He was even closer friends with William “Billy” Bulger, Whitey’s younger brother, who would rise through the political ranks to become president of the state Senate and, arguably, the most powerful politician in the Massachusetts 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 apparently was concerned might cooperate with a criminal investigation. Callahan was shot in the head by a Bulger associate and 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 10 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.

whitey-bulger-FE03-secondary Scenes from Bulger’s reign of terror: A Tulsa, Okla., businessman gunned down Boston Herald-Polaris

Says Connolly, “[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 it to me 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.”

Between 1975, when Connolly first enlisted Bulger as a top-echelon informant (TE), and 1990, when Connolly 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 underway. He had a friendly conversation with Sen. 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 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 nearly the entire Boston office and regional supervisors of the FBI, but also stretched into the U.S. attorney’s office and possibly involved federal judges.

Federal prosecutors would seem to be on 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 go 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 run 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 Patriarca’s home in Providence, R.I., and documented on tape a conversation in which 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.

whitey-bulger-FE03-third Scenes from Bulger’s reign of terror: The remains of Debra Davis, who Bulger allegedly strangled. Mark Garfinkel / Boston Herald-Polaris

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.

By the time John Connolly recruited and signed up Whitey Bulger as an FBI informant in the mid-1970s, the Boston underworld had descended into a murky, murderous pit of rats, with cops and federal agents as active players. Connolly’s predecessor and mentor in the Boston FBI office, Special Agent H. Paul Rico, would eventually be indicted on charges of obstruction of justice and murder. Rico was believed to have supplied key information for gangland murders, and may have even taken part in actual mob hits himself. He died in prison in January 2004 while facing prosecution.

The Boston FBI office has been publicly excoriated for its handing of Bulger and Flemmi, and rightfully so. Connolly and many others in law enforcement defend the concept of using criminals to catch other criminals: “Nobody wants to see how the sausage is made, but in the real world that’s how cases get made,” says Connolly. At the very least, the Bulger case reveals a shocking lack of oversight. Federal agents fed information to two mobsters that led to murders and the thwarting of potential criminal investigations spearheaded by other law enforcement agencies. They helped turn Bulger and Flemmi into the most powerful gangsters in the history of Boston.

Connolly’s supervisor, special agent John Morris, head of the organized-crime squad, pleaded guilty to charges of accepting bribes and gratuities from Bulger, and obstructing justice. He served no jail time in exchange for testifying at 1998 hearings into the Bulger affair. In his testimony, Morris put forth a scenario—since expounded upon by prosecutors and the media—that Connolly was a “rogue agent” who promoted and protected Bulger’s informant status within the bureau solely for personal profit and aggrandizement.

Connolly is not without culpability, but he did not devise the Top Echelon Informant program, and whatever he did to maintain Bulger’s viability as an informant was authorized and in many cases rewarded via promotions and special citations from six different FBI directors.

“There were enablers throughout the system, from top to bottom,” says retired FBI agent Robert Fitzpatrick. An assistant special agent in charge of the Boston office, Fitzpatrick was Connolly’s nemesis. After meeting Bulger and Connolly together, Fitzpatrick recommended that Bulger be “closed down” as an informant. His recommendations were ignored and his two-page report about Bulger was buried by two successive special agents in charge of the Boston office. Over time, Fitzpatrick began to sense that the conspiracy to protect Bulger went all the way to headquarters in Washington, D.C. His suspicions were later verified in U.S. congressional hearings that concluded, “What happened in New England over a 40-year period is, without doubt, one of the greatest failures in federal law-enforcement history.”

That conspiracy went beyond the FBI. Among the friends of Whitey Bulger who ran interference for the mobster was Jeremiah O’Sullivan, head of the U.S. attorney’s organized crime strike force, who would, thanks to his successes during the Bulger years, rise to become U.S. attorney in Boston.

As early as 1977, agent Connolly informed O’Sullivan that he had “turned” someone who could help them make major cases against the Mafia. When O’Sullivan heard it was Bulger, he wanted to meet him. Remembers Connolly, “I asked him, ‘Are you sure? You don’t have to.’” It was highly unusual for an assistant U.S. Attorney to meet face to face with a top informant while an investigation was still ongoing. O’Sullivan insisted. Connolly set up a meeting between the city’s top mobster and its top organized crime prosecutor in a hotel room on a rainy afternoon around Christmas. “I was there,” says Connolly. “Jimmy met Jerry. As I remember it, they were both quite impressed with one another.”

O’Sullivan was one of the best things that ever happened to Bulger. In 1979, when an investigation targeted an array of mobsters on charges of fixing races at horse tracks, O’Sullivan dropped Bulger and Flemmi from the indictment. As Flemmi would later put it, “We believed we were authorized to commit crimes as long as we didn’t kill anybody. That’s what we were told.”

O’Sullivan’s desire to protect his prize informants didn’t end with Whitey and Stevie. In 1989 information was brought to O’Sullivan that Sen. Billy Bulger had received a legally questionable payment of $240,000 as part of a real-estate deal at 75 State Street in downtown Boston. According to Bob Fitzpatrick, who investigated the deal, “It was a clear violation of the Hobbs Act. We had Billy Bulger dead in his tracks.” But O’Sullivan made the decision not to go forward with charges against Senator Bulger. After the deal was exposed by the media, Bulger returned the money.

For those few within the system who were privy to these deals, it seemed like a case of garden-variety corruption. In 2003, long after Bulger went on the run and his associates began cutting deals with the government, pieces of the puzzle began to fall into place. Hearings were held by the U.S. House Committee on Government Reform that proved to be an unprecedented foray into the criminal history of the Bulger era. The hearings most famously exposed Billy Bulger, who was forced to resign from his job as president of the University of Massachusetts after it was revealed he had been in contact with his fugitive brother.

Far more revealing was the testimony of O’Sullivan, also retired, who, in the years since Bulger’s disappearance, had publicly denied that he’d known that Bulger was an informant until he read about it in the press. This bold-faced lie was exposed when internal Justice Department memos were produced that showed O’Sullivan had known about Bulger since the late-70s. “You got me,” said the former U.S. attorney to the congressional committee.

Even more damaging were FBI and DOJ memos and correspondence subpoenaed by the committee, after a fierce legal battle with the Bush administration. Records showed that O’Sullivan’s mentor and predecessor as U.S. attorney, Edward Harrington (later a federal judge), had been complicit in the framing of Limone and Salvati for the Deegan murder. At the hearings, a picture began to emerge of a generation of agents and prosecutors who were the metaphorical offspring of those who had conspired to make sure that the truth about the Deegan murder would never be revealed. Thus, protecting Bulger and Flemmi became a way of repressing this potentially explosive history: Whitey and Stevie became the keepers of the Justice Department’s dirty little secret.

A final report on the findings of the House committee was issued in 2004. Entitled “Everything Secret Degenerates: The FBI’s Use of Murderers as Informants,” it remains the most detailed exposé on the Bulger era. The findings helped expedite a financial settlement for Peter Limone and Joe Salvati, who had their convictions overturned in 2000. In 2007 they were awarded $101.7 million in damages—paid by U.S. taxpayers—for having unjustly served 34 years in prison. The U.S. government has also been forced to pay, collectively, $20 million in damages to family members of some of Bulger’s victims, who filed suits against the FBI and DOJ, claiming that the man who killed their loved ones did so while being sponsored and protected by the government.

Those who advocate for the U.S. attorney’s current streamlined prosecution of Bulger make the argument that the conspiracy has been fully aired at various hearings and trials in the 16 years that Bulger was basking in the California sun. In 1999 the Justice Department claimed it was going to get to the bottom of the Bulger fiasco and that no one would be spared. John Durham, a Connecticut prosecutor, was appointed by Attorney General Janet Reno to spearhead an investigation, but the Durham report was never completed or delivered, and the government has never explained why. The sole significant result of Durham’s efforts was the prosecution of John Connolly.

Despite decades of corruption, obstruction of justice, and suppression of evidence, no government official in a supervisory position has ever been held accountable. Many who benefited most from Bulger’s tenure as an informant have since passed away.

Some doubt that a trial will ever come to pass. Bulger may choose to stall and run out the clock and eventually die in prison, though his lawyer denies that is the case. The prosecution—while claiming to proceed—also has reasons not to be overly enthusiastic about a trial, given the potential for unanticipated revelations.

Amid the uncertainty, one thing is clear: as the U.S. Justice Department prepares to put on trial one of the most murderous gangsters in the last half century, it is in no position to claim the moral high ground.