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Federal Bureau of Investigation

Legendary Boston gang boss Whitey Bulger faces trial

William M. Welch
USA TODAY
  • Whitey Bulger faces multiple counts of murder%2C other crimes
  • Captured after 16 years on the lam%2C he spent most of that time by a California beach
  • FBI%27s role in cooperating with Bulger likely to be aired
Prosecutors say James "Whitey" Bulger, one of the FBI's Ten Most Wanted fugitives, was a Boston mob boss.

Once the feared titan of Boston's old Irish Mob who ruled the tough side of town with thuggish impunity, James "Whitey" Bulger goes in front of a jury this week to face the reckoning he ran from nearly two decades ago.

Now a bearded old man of 83, Bulger hardly looks the ruthless crime boss — and secretly protected FBI informant — that prosecutors allege.

Before he fled Boston in 1994 and spent 16 years on the lam, they say, he ran a criminal operation known as the Winter Hill Gang with a brutality that terrorized South Boston in the 1970s and '80s.

He faces a 32-count federal indictment alleging that, among other things, he participated in 19 slayings going back to the early '70s, as well as racketeering, extortion, weapons offenses and money-laundering. After more than a week of jury selection, lawyers are set to make their opening statements Wednesday.

The trial may stir old ghosts, giving a public airing to the corruption that infected the city and even the FBI during the years he was in charge.

"Sure, Whitey Bulger is on trial, a compelling and significant crime figure,'' said Dick Lehr, a Boston University journalism professor who has authored two books on the fallen crime boss.

"But the FBI is also on trial. You cannot mention Whitey Bulger without in the same breath talking about the FBI,'' Lehr said. "It wasn't a single case. ... It was a way of life for a couple decades.''

Even as the carnage mounted, Bulger was a bigger-than-life figure in Boston, a widely known, politically connected guy whose own brother, Billy, was president of the state Senate and eventually president of the University of Massachusetts.

There was even a bit of a Robin Hood myth surrounding Bulger, a local tough who climbed to the top of the heap while maintaining ties to the working-class folks back in Southie and the public housing project where he grew up. He was the inspiration for Jack Nicholson's mob boss character in the 2006 Martin Scorsese film The Departed.

But federal indictments tell a sordid tale of extortion, shakedowns and murders of rivals and potential witnesses. Among the 19 slayings he is accused of was the 1981 strangulation of Debra Davis, allegedly because she planned to break up with Bulger's partner in crime. Federal prosecutors allege he buried three other victims in the yard of a South Boston home, then dug them up and reburied them at another property when they learned the house was being sold.

Most, but not all, of the slayings were in the Boston area. He was accused of conspiring to kill Roger Wheeler, owner of World Jai Lai, who died in May 1982 at Southern Hills Country Club in Tulsa.

Bulger fled Boston in 1994 after being tipped off that he was about to be indicted — a favor from his pal and former FBI handler, John Connolly. Connolly, who grew up in the same South Boston housing project as Bulger, recruited him as an informant and protected him from prosecution in exchange for tips, jurors found in Connolly's 2002 trial, when he was convicted of racketeering, obstruction of justice and lying to the FBI. He received a 10-year prison sentence. In 2005, Connolly was convicted in Florida of murder; he was accused of tipping Bulger and Flemmi, who allegedly then had a potential witness against them killed. He is serving a 40-year sentence on that conviction.

Bulger was captured in June 2011 in Santa Monica, Calif., where he had spent most of the previous 14 years before a renewed federal dragnet with a $2 million bounty produced the tip that brought him down. The FBI renewed its hunt for Bulger by airing public service announcements in several states, including California, focusing on the search for his companion, Catherine Greig, and appealing to those who might have seen her at a beauty parlor or doctor's office. Within days, the FBI received hundreds of tips. The reward money was paid to a former Miss Iceland 1974, Anna Bjornsdottir, who had gotten to know Bulger's girlfriend while living in Santa Monica, the Boston Globe reported in 2011.

While on the FBI's 10 Most Wanted list, Bulger had been hiding in plain sight — using a fake ID, covering his bald head with a Red Sox cap and walking daily along the Pacific surf far from the harsh winters of his hometown.

Sharing his $1,100-a-month rent-controlled apartment three blocks off the beach was Greig, who was a 46-year-old gangster's moll when she skipped town with him. Cops found an arsenal of guns and $822,000 in cash hidden behind the walls.

Greig, 62, is serving an eight-year sentence after pleading guilty last year to conspiracy to harbor a fugitive and identity fraud.

The trial is expected to last as long as three months. U.S. District Judge Denise Casper ruled jurors won't be sequestered and their identities will be released after a verdict. Lehr said that shows Bulger has no organization or loyal enforcers left to fear.

Bulger, who has previously done time in Alcatraz and Leavenworth federal prisons for bank robbery, has pleaded not guilty and through his lawyers denied being the FBI's informant.

Prosecutors plan to call notorious gangsters and hitmen to testify against him, including John Martorano, who admitted killing 20 people, and Steven "The Rifleman" Flemmi, serving a life sentence for 10 deaths.

Bulger's defense lawyers said in a recent court filing that they will attack the credibility of the prosecution witnesses, who were once reviled and sent to prison by the same government.

Bulger is accused of playing a double game, tipping the FBI about criminal activities, including those by a rival Italian-American gang, while running his own Irish-American network of shake-down artists, loan sharks and enforcers. Prosecutors allege Bulger controlled illegal activity in South Boston, extorting "street rent" from drug dealers, bookies and other criminals, while his tips allowed the FBI to dismantle the Italian Mob in New England.

It was an unholy alliance, said Lehr, "a devil's deal with the Boston FBI office'' that "enabled Whitey and protected him, once established as the local crime boss.''

Attorney Barry Slotnick, who defended mobsters John Gotti and Joe Colombo, said the passage of time, Bulger's age and grandfatherly appearance, and disputes over the extent of his cooperation with the FBI could make it difficult for prosecutors to win a conviction.

"There is a very good possibility he will get acquitted,'' Slotnick said. "He hasn't been involved in criminal activity for a long time.''

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 FBI, including that he was never an informant,'' attorney J.W. Carney Jr. told the Associated Press before the trial began.

But in an as-yet-unexplained contradiction, Bulger also is arguing he had immunity because of his work for the government. Casper has ruled that any purported immunity deal was "not a defense to the crimes charged.''

Defense attorneys said they plan to call top law-enforcement officials, including FBI Director Robert Mueller, former Massachusetts Republican governor William Weld and U.S. District Judge Richard Stearns, each of whom worked in the U.S. attorney's office in Boston during Bulger's reign on the streets.

Lehr, whose latest book is Whitey: The Life of America's Most Notorious Crime Boss, says some of the slayings Bulger is accused of playing a role in were "tip-off murders,'' where victims were targeted after the FBI tipped Bulger that they were cooperating with law enforcement.

Survivors will be watching Bulger closely inside the courtroom.

More broadly, his victims may be viewed as the city itself, even South Boston, the once tough, overwhelmingly white side of Boston that has moved upscale and grown more diverse since Bulger's days.

And the city's faith in its institutions: "The damage to law enforcement ... still exists today,'' Lehr said. "The good guys were bad guys and the bad guys were in charge.''

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