As Whitey Bulger trial opens in Boston, prosecutor describes a ‘hands-on killer’


James "Whitey" Bulger, center, depicted in a courtroom sketch during a June 3 pretrial conference before U.S. District Judge Denise Casper, left rear, in a federal courtroom in Boston. Bulger is flanked by his attorneys Henry Brennan, left, and J.W. Carney Jr., standing at right. (Jane Flavell Collins/Associated Press)

James “Whitey” Bul­ger is an old man now.

He wears reading glasses. His hair is pure white, but not much remains. And when he stood up in a federal courtroom Wednesday morning to finally face the music, to stand trial for a lifetime of gangster crimes, he rose slowly, no longer the menacing Irish mob boss who allegedly scratched out 19 lives while the FBI looked the other way.

Wearing a long-sleeved green shirt, jeans and sneakers, Bulger sat passively as a prosecutor described his younger, more sinister years as leader of the Winter Hill Gang, including the time he allegedly marched a safecracker named Arthur “Bucky” Barrett to a set of cellar stairs after torturing him in a chair in pursuit of $40,000 from a bank robbery.

“Barrett’s going downstairs to lie down for a while,” Bulger told an accomplice, according to the chilling story federal prosecutor Brian Kelly recounted for jurors Wednesday during his opening statement. Then Bulger shot him in the back of the head, leaving his underlings to dig a grave while he rested on a sofa.

“He was no ordinary leader,” Kelly said. “He did the dirty work himself. He was a hands-on killer.”

After being on the run for 16 years, Whitey Bulger was captured by the FBI 2011. He now stands trial for 19 alleged murders.

Now 83, sitting in a courtroom not far from his old hangouts, Bulger looked like a senior citizen waiting patiently for results from a doctor. His meek return after skipping town in 1994 on the advice of a corrupt FBI agent opens the final chapter in a seemingly preposterous life story. Bulger helped FBI agents bring down the local mafia, and they in turn helped him avoid prosecution. He controlled the Boston underworld while his little brother controlled state politics. He was turned in by an Icelandic ex-beauty queen.

“What’s been true about this case for decades is that it really exceeds the capacity of human imagination,” said Harvey Silverglate, a Boston criminal defense lawyer.

The terrifying richness of Bul­ger’s life laid bare in a courtroom threatens to embarrass the FBI and Justice Department, which Bulger said promised him immunity for his crimes. But the trial is also about a largely bygone time. Big gangster trials are a rarity these days. The FBI has largely moved on from organized crime — if there even is much left — to focus on terrorism.

“If you go back to the ’70s and ’80s and asked who was the most powerful person in a city, there would be a godfather that everyone would know,” said James Jacobs, an organized-crime expert at New York University law school. “These godfathers were at the core of the power structure of American cities. I don’t think that really exists anymore.”

Today, big-screen box office hits are about the hunt for Osama bin Laden, not mobsters like Paul “Paulie” Cicero in “Goodfellas.” But the color of old gangster movies is back with the Bulger trial. There’s Stephen “The Rifleman” Flemmi, a former army sharpshooter and partner in crime, who is scheduled to testify against Bulger. And on Wednesday, a former state police detective testified about an old organized-crime investigation dubbed “Operation Lobster.”

Both sides of the law

Bulger rose to power with the help of FBI agent John “Zip” Connolly, who grew up near Bul­ger in the hardscrabble housing projects of South Boston and once was even given an ice cream cone by the older boy. They hooked up as adults with a shared interest in bringing down the New England Mafia — Connolly because of the FBI’s obsession in the ’70s and ’80s with Italian organized crime, and Bulger because it was his primary competition.

As Bulger netted millions of dollars in extortion, gambling and drug dealing — his attorney didn’t deny these criminal undertakings during opening statements — FBI agents, including Connolly, provided cover in exchange for his help with the local mafia, according to a lengthy ruling by a Boston federal judge and other investigations through the years.

A 2004 report by the House Committee on Oversight and Government Reform found “no doubt” that law-enforcement personnel, including FBI officials, were aware that informants, including Bulger, “were committing murders.”

Keith Ausbrook, who had been the chief counsel for the committee, said in a recent interview that “you don’t expect your informants to be angels, but you don’t expect them to be murderers either. And you certainly hope the FBI’s not helping them.”

But agents were. Connolly tipped off Bulger to a looming indictment. He was found guilty in 2002 on federal charges related to his partnership with Bulger. Connolly is serving 40 years in prison for second-degree murder after he gave information to Bulger and Flemmi that resulted in them urging a hit man to kill a witness.

Bulger’s attorney, J.W. Carney Jr., argued in early motions in the case that Bulger had received immunity for his crimes from federal officials. U.S. District Judge Denise J. Casper ruled that such a defense was not admissible. During his opening statement, Carney said that Bul­ger was never an informant and that he had simply paid off police and FBI agents.

“The evidence will show that he was never an informant,” Carney said, a statement that drew audible laughter from reporters covering the trial.

Kelly, the prosecutor, said, “Even though you will hear he didn’t like informants or rats, the evidence in this case will be that Bulger was one of the biggest informants in Boston.”

A life on the lam

Bulger’s career in the city’s underworld ran parallel to his brother’s rise as one of the most powerful politicians in Massachusetts. William Bulger was president of the state Senate for nearly two decades and later president of the University of Massachusetts.

But in 2003 William Bulger left U-Mass., and public life, following a battle with then-governor Mitt Romney over his loyalty to his gangster brother. According to leaked testimony, William Bulger had told a grand jury that “it’s my hope that I’m never helpful to anyone against him.” He invoked his Fifth Amendment right against self-incrimination during the House committee hearings. He later testified after being granted immunity.

William Bulger was not in court Wednesday morning.

Bostonians have for decades been consumed with a question that showed up on T-shirts and book covers: “Where’s Whitey?” Although the FBI had been accused of not wanting to find Bulger, perhaps for fear he would disclose more corruption, the agency renewed efforts to find him several years ago.

There had been alleged sightings around the world, but it turned out Bulger and one of his longtime girlfriends had been living the life of retirees in Santa Monica, Calif. He was turned in by a former neighbor, the ex-beauty queen from Iceland. She received a $2 million reward.

Carney said Bulger, then on the FBI’s 10 Most Wanted list, was not hiding in California. In fact, the lawyer said, he was living in “plain sight.” But Carney did not mention that Bulger was living under an assumed name with false identification and dozens of weapons — and $800,000 in cash — stashed in the walls.

The story of Bulger’s extraordinary life is being turned into two movies, one by Barry Levinson, the other by Ben Affleck and Matt Damon, who chronicled working-class life in their home town in “Good Will Hunting.” The fascination with the Bulger case across broad swaths of city life was apparent during jury selection, when several potential jurors said they had read “Black Mass,” a bestselling book about Bulger by two former Boston Globe reporters.

But there is also disdain for Bulger and what he did to the community. When asked to comment on Bulger’s life and trial and what it means for Boston, Dennis Lehane, a local crime novelist and author of “Mystic River,” declined.

“I don’t give Whitey free press,” he said through his assistant.

Asked the same question, Mona Connolly Casper, the president of the South Boston Irish American Society, said: “Nope, not a chance, not at all.”

Michael Rosenwald is a reporter on the Post's local enterprise team. He writes about the intersection of technology, business and culture.
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