With long odds, Bulger will have his day in court

List of charges — including 19 killings — is extensive as the trial opens this week

Stephen “The Rifleman” Flemmi testified that he watched as James “Whitey” Bulger strangled his girlfriend, Debra Davis, shown here with Flemmi in the late 1970s.
Stephen “The Rifleman” Flemmi testified that he watched as James “Whitey” Bulger strangled his girlfriend, Debra Davis, shown here with Flemmi in the late 1970s.

James “Whitey” Bulger calls it “The Big Show,” his chance to vindicate himself after years of being portrayed in court proceedings, hearings, and books as a depraved gangster who strangled women, corrupted FBI agents, and informed on his friends.

“Want to refute lies + try to get my name cleared,’’ Bulger wrote to a friend from jail last year in a letter that was shared with the Globe.

But refuting the evidence laid before the jury in his long-anticipated trial, expected to begin with jury selection in US District Court in Boston on Tuesday and to run through the summer, will be an enormous task even for a man as cunning and as resourceful as Bulger, legal experts say.


The former South Boston gangster is facing 32 counts in an indictment that relies on federal racketeering laws, which allow prosecutors to pull in crimes that are well past the statute of limitations and to include murders, generally the jurisdiction of state courts. The indictment alleges that while running a criminal enterprise from 1972 to 2000, Bulger killed 19 people; extorted money from more than a dozen drug dealers, bookmakers, and businessmen; corrupted FBI agents and other law enforcement officials; laundered his illegal profits; and stockpiled an arsenal of weapons. The 32 counts include: racketeering conspiracy, racketeering, extortion conspiracy, extortion, money laundering conspiracy, 22 counts of money laundering, and five firearms counts.

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Prosecutors are poised to call 80 witnesses and offer about 1,000 exhibits. The defense says Bulger, now 83, will take the stand, along with as many as 78 defense witnesses.

“Racketeering gives the government a unique advantage to package different types of crimes that otherwise could not be charged together,” said Martin Weinberg, a prominent Boston criminal defense attorney. “He’s going to be subject to a trial that may focus on murder, but he’ll also be required to defend against drug dealing, money laundering, firearms. . . . Jurors are going to be burdened with an overwhelming amount of evidence that Whitey Bulger made and spent huge amounts of money.”

Bob Dean/Globe Staff/File 1979
Former FBI supervisor John Morris (second from left) admitted to taking $7,000 in bribes from Bulger and Flemmi and leaking them information.

In Bulger’s case, the racketeering conspiracy count alleges he and other members of his gang participated in 33 criminal acts, including the murders and various extortions. Jurors will be asked to reach a unanimous verdict on each of the 33 acts, but must only find Bulger guilty of two to convict him of racketeering conspiracy. He faces life in prison if found guilty of even one murder. Yet, even a conviction for illegal weapons possession could effectively send Bulger to prison for life, given his age.

And after this trial, Bulger still faces murder charges in Oklahoma and Florida that carry the death penalty.


“I think it’s impossible for him,” said Boston criminal defense attorney Anthony Cardinale. “It’s not like there’s one big witness against him. There’s so many and they’re all interconnected and they all corroborate each other.”

The murder victims include two young women, three FBI informants, a Tulsa millionaire who suspected Bulger’s gang of skimming money from his company, a young father who had the misfortune of giving a ride home to a man who was allegedly Bulger’s intended target, and a bartender who was mistaken for someone else.

For families of victims, trial is a victory in itself

New Hampshire attorney William Christie, who represented the families of two of Bulger’s alleged victims in wrongful death suits against the government, said he believes the prosecution’s case is strong. But he said that, whatever the outcome, the satisfaction of finally seeing Bulger stand trial is a huge victory.

“Everybody believes Bulger was the kingpin behind all of this,” Christie said. “People want to see him brought to justice.”

In this photo taken in 1994, James “Whitey” Bulger (left) and Kevin Weeks walked around Castle Island in South Boston. Weeks, a Bulger protégé who admitted assisting in five murders, will be a key witness for the prosecution.

Bulger fled shortly before he was indicted in January 1995 on charges that he, his sidekick Stephen “The Rifleman” Flemmi, then-New England Mafia boss Francis “Cadillac Frank” Salemme, and others were part of a racketeering enterprise that controlled illegal gambling and loansharking in Greater Boston.


But that case began unraveling when Flemmi moved to dismiss the indictment in 1997 on the grounds that he and Bulger couldn’t be part of a conspiracy with the Mafia because both were longtime FBI informants who were promised immunity for their crimes in exchange for their cooperation against local mob leaders. A judge rejected Flemmi’s immunity claim and refused to dismiss the case, but not before holding lengthy hearings exposing the FBI’s corrupt relationship with the two gangsters.

‘Mr. Bulger believes that he will have a fair trial if he is able to present the whole truth concerning his relationship with the Department of Justice and the FBI.’ — J.W. Carney Jr. , lawyer representing James “Whitey” Bulger, who denies that he was an informant for the FBI

The FBI acknowledged that Bulger had been an FBI informant from 1975 to 1990, and Flemmi since the 1960s, and much of their informant files were made public. Former FBI supervisor John Morris admitted taking $7,000 in bribes from the pair and leaking them information. In the decade that followed, Bulger’s closest associates turned on him, became government witnesses, implicated Bulger in numerous slayings, and led investigators to secret graves. His former FBI handler, John J. Connolly, was convicted of warning Bulger to flee before his indictment and of second-degree murder for leaking information to Bulger and Flemmi that caused the 1982 slaying of a Boston businessman in Florida. Connolly is serving 40 years in prison.

In 2000, Bulger, then one of the FBI’s 10 Most Wanted, was charged in the sweeping federal racketeering indictment for which he’s about to stand trial. The earlier case was dismissed two years ago.

Years on the lam end when Bulger is caught

Many of the families of Bulger’s alleged victims had given up hope that he would ever be caught, when on June 22, 2011, he was captured in Santa Monica, Calif., where he had been living in the same rent-controlled apartment with his longtime girlfriend, Catherine Greig, for 15 years.

Steve Davis plans to attend the trial every day. He is sure Bulger will be convicted of killing his sister Debra.

The dramatic courthouse showdown that begins this week will pit Bulger against his old partner, Flemmi, who pleaded guilty to participating in 10 murders with Bulger as part of a deal that sent him to prison for life but spared him the death penalty. Three other key government witnesses will be Morris, the corrupt FBI supervisor who was granted immunity from prosecution; John Martorano, a hitman who admitted participating in 20 murders and served 12 years in prison; and Kevin Weeks, a Bulger protégé who admitted assisting in five murders and served five years in prison. All are experienced witnesses whose testimony helped send Connolly to prison.

“I’m the Last Man Standing and all these guys made deals that Donald Trump couldn’t at my expense,” Bulger wrote last year in a letter to an old friend, Richard Sunday, from the Plymouth County Correctional Facility, where he is being held in segregation.

Bulger, more than anything, according to his letters, wants the world to believe that he was not an informant and that he did not strangle the two young women, Debra Davis and Deborah Hussey, who are among his 19 alleged victims.

One of Bulger’s lawyers, J.W.Carney Jr., said in an e-mail to the Globe: “Mr. Bulger believes that he will have a fair trial if he is able to present the whole truth concerning his relationship with the Department of Justice and the FBI, including that he was never an informant.”

Alleged Bulger victim John McIntyre’s family won a wrongful death case against the government.

During interviews with the Globe in 1998, Connolly, who grew up in the same South Boston housing development as Bulger, said that he recruited Bulger as an informant in 1975 but that the gangster preferred to be called a “strategist” or “liaison.”

Carney said Bulger wasn’t prosecuted for 25 years because he had an immunity agreement with the Justice Department.

Bulger said he was promised immunity from prosecution decades ago for all crimes, past and future, including murder, by Jeremiah T. O’Sullivan, a federal prosecutor who headed the New England Organized Crime Strike Force. O’Sullivan died in 2009.

US District Judge Denise J. Casper, who is presiding over the trial, rejected a request by Bulger to present evidence of his immunity claim to jurors, concluding that even if O’Sullivan had made such a promise, he did not have the authority to do so.

Still, Bulger’s relationship with the FBI and the Justice Department will remain a major issue at trial. Prosecutors allege that Bulger and Flemmi evaded prosecution for years because Connolly and Morris leaked them information about ongoing investigations. They also allege that Bulger and Flemmi orchestrated the murder of three FBI informants after Connolly warned them that the men were cooperating against them or their gang.

Flemmi previously testified that Bulger insisted they kill Flemmi’s 26-year-old girlfriend, Debra Davis, in 1981 because she was leaving him for another man and knew about the corrupt relationship between the two gangsters and the FBI. Flemmi said that he lured Davis to a vacant South Boston home he bought for his elderly parents, then watched as Bulger strangled her. Bulger vehemently denies strangling Davis, and Flemmi remains the sole witness against him.

In a nearly identical scenario, Flemmi testified that he lured another woman, Deborah Hussey, also 26, to a different South Boston home in January 1985 and again, watched as Bulger strangled her. Bulger has also strongly denied killing Hussey, who was the daughter of Flemmi’s longtime live-in girlfriend.

Davis’s brother, Steve, who has been waiting for Bulger’s trial for years and plans to attend it every day, said he believes the evidence is strong and is confident Bulger will be convicted of killing his sister.

“I would be disappointed if it was ruled any other way,” Davis said. “I wouldn’t even have words for it. There’s no way this man is walking free.”

Christie, one of the lawyers who won a $3.1 million wrongful death judgment from the government for the family of alleged Bulger victim John McIntyre, said they proved in the civil case that Bulger’s criminal enterprise could not have existed for so long without the complicity of the FBI and the Department of Justice.

But, Christie said, “I don’t think a jury will say: The government is corrupt so we’re going to find Bulger not guilty.”

Shelley Murphy can be reached at