The Whitey Bulger Trial: A Six-Point Primer

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AP / Federal Court Documents

This undated photo filed in federal court documents in Boston by defense attorneys for James "Whitey" Bulger on Wednesday, July 31, 2013, shows Bulger with holding a goat in an unknown location.

Jury selection for the trial of James “Whitey” Bulger, one of the most infamous figures in organized crime history, begins today in a Boston courthouse. The high-profile trial of the accused mobster is expected to bring out a who’s-who of convicted underworld figures, including many from the criminal organization known as “Winter Hill” or “South Boston,” according to the Boston Globe. It will also provide the most comprehensive account to date of the myriad crimes Bulger has been accused of, including the 19 murders he’s been linked to.

The reputed mob figure, whom some suggest was the inspiration for Jack Nicholson‘s character Frank Costello in Martin Scorsese’s The Departed, has been on the lam since 1994 after an FBI mole tipped him off that law enforcement was getting close to an indictment against him. After Bulger settled with girlfriend Catherine Greig in Santa Monica, Calif., the two lived under assumed names and pretended to be a retired couple. He was finally captured in 2011 and placed in federal custody to await trial on charges laid out in a 111-page indictment.

Here are the six things you should know about Bulger’s case:

How did Whitey Bulger get started?

Born in 1929 and raised in a housing project in Boston’s gritty Dorchester neighborhood, Bulger was in and out of jail since he was a teenager for crimes ranging from robbery to assault. After serving nine years in federal prison (including a stint at Alcatraz) for a 1956 robbery, he returned to Boston in 1965 and allegedly got involved with the mob, eventually becoming the right-hand man to gangster Howie Winter.

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How did Bulger rise to the top of Boston’s Winter Hill gang?

By the early 1970s, Bulger had allegedly partnered with Stephen “the Rifleman” Flemmi to run an extravagant racketeering enterprise that took over much of the gambling, loan sharking and drug activity in Boston. By the mid-1970s, both Bulger and Flemmi had become FBI informants, according to Boston.com, while continuing their criminal activities. By 1979, after Winter Hill leader Howie Winter was convicted in a horse race-fixing scam, Bulger and Flemmi were running the gang.

What are some of the murders that Bulger is facing trial for?

In 1981, Bulger and Flemmi allegedly ordered a hit on Roger Wheeler, owner of the betting company World Jai Alai. The next year, they allegedly kill one of their own gang members keep him from ratting them out. Because Bulger and Flemmi were still under protection as FBI informants, FBI agent John Connolly filed a false report saying that rival gangsters committed the crimes. Later on, Bulger and Flemmi are said to have ordered a hit on the president of Wheeler’s company, also to keep him quiet. In 1990, Connolly left the FBI, and the agency went after Bulger and Flemmi. In late 1994, though, he tips Bulger off that authorities are after him. Flemmi is captured and after six years of trials, he strikes a plea deal and is sentenced to life imprisonment for 10 murders. Bulger goes on the run, vanishing the night before he was to be indicted.

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Don’t FBI informants get protection? If so, why did Bulger have to go on the lam?

Yes and no. In 1979, Bulger escaped indictment because he was an informant, and the FBI didn’t want to lose the stream of valuable information he provided. But that didn’t get either Bulger or his associate Flemmi off the hook, because a judge ruled that they were never guaranteed immunity. Connolly, the corrupt agent who had offered the pair protection, was convicted in 2002 of racketeering, informing Bulger and Flemmi about their criminal investigations and lying to his bosses. He was also convicted in Florida on second-degree murder charges and is serving a 40-year sentence.

How was Bulger captured?

In 1995, Bulger and his girlfriend Catherine Greig assumed the aliases Charlie and Carol Gasko and moved into a rent-controlled apartment complex Santa Monica, Calif. Grieg told neighbors that her “husband” had Alzheimer’s disease, and she was known to feed a stray cat and take it to the veterinarian. Neighbors reportedly regarded them as a kind, old couple. That kindness caught the attention of Anna Bjornsdottir, a former actress and Miss Iceland, who often chatted with Bulger’s girlfriend while she fed the cat. In 2011, after seeing pictures of him on CNN, which had been covering the manhunt, Bjornsdottir contacted the FBI, who instantly took Bulger and Grieg into custody. Grieg was sentenced to 8 years behind bars for aiding Bulger. Bjornsdottir reportedly got $2 million for tipping off the FBI.

(MORE: Whitey Bulger’s Life on the Lam: Rage and Dementia?)

What can we expect to find out in his trial?

The federal indictment against Bulger denotes numerous, graphic details about the 19 murders Bulger has been linked to and is expected to expose corruption within the FBI related to the case. Defense attorneys are expected to file motions that would limit the testimonies of the victims’ relatives and cast a negative light on law enforcement for allowing underworld figures to continue to operate while under their protection, according to the Boston Herald. Bulger also faces multiple racketeering charges, but if convicted of some or all of the 19 murders, he’ll almost certainly face the death penalty.