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Mob Secrets Exposed

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For decades he’d been James “Whitey” Bulger’s No. 2 in the Winter Hill Gang, Boston’s notorious Irish mob. But when Stephen Flemmi recently took the stand to testify against his former boss, he unleashed a verbal barrage worthy of his own nickname “the Rifleman.” His contempt dripping for the balding, bespectacled Bulger, 83, Flemmi cut right to the chase. Asked the nature of their relationship, he responded, “Strictly criminal.” In precise, often chilling detail, Flemmi then described nine murders that he said he and Bulger had ordered, approved or carried out in the 1970s and ’80s, among them the 1981 slaying of his own girlfriend Debra Davis, 26, a death that he said Bulger had ordered after Flemmi “blurted out” to her that he and Bulger were FBI informants. Flemmi, who at one point called Bulger a choice expletive, testified that after he lured Davis to his mother’s house, Bulger “grabbed her around the throat and strangled her.” And what had Flemmi done? “Nothing.” Why? “That was the plan.”

If none of the slayings hit closer to home for Flemmi, none cut closer to the heart for Bulger. Six weeks into his sweeping federal racketeering trial, the mob boss has made clear that, more even than wanting to clear himself of 32 alleged crimes – among them 19 murders, extortion and money laundering – Bulger wants to clear his reputation of the noncriminal charge that in the Irish underworld applies only to the lowest form of pond scum: snitch. Described from the witness stand by a former FBI supervisor as having provided information about a mob associate, Bulger exploded, “You’re a [expletive] liar!” For crime-show fans, the colorful drama inside Boston’s austere John Joseph Moakley U.S. Courthouse couldn’t be beat, that is until Stephen “Stippo” Rakes, 59, one of Bulger’s accusers, was found dead on July 17. While one police source told reporters the death was suspicious, Stephanie Guyotte, spokeswoman for the Middlesex County DA’s office says,”We’re not saying it’s suspicious. We’re just investigating the death.”

Decades ago Rakes had charged that Bulger forced him in 1984 to sell his liquor store at below-market value so that the mob could use it as a front, an extortion that he claimed involved seating Rakes’s 1-year-old daughter on a mobster’s knee and letting her play with a gun. Rakes had gotten no satisfaction in criminal court, but he’d won a $28 million judgment against Bulger in a civil suit. In the current trial, he was raring to refute testimony that he’d wanted to sell his store. Rakes “told me his testimony was going to be a bombshell,” says Steven Davis, 55, brother of Flemmi’s slain girlfriend Debra, who’s been attending the trial. But on July 16, Rakes was stricken from the prosecution’s witness list. A day later he was found dead along a walking path in Lincoln, Mass., seven miles from his car, no telltale marks on his body. With the results of a toxicology screen still days, maybe weeks, away, Bulger supporters have been speculating that the cause of death was natural causes or suicide by drugs. With Rakes already removed from the witness list, says one insider close to Bulger, “there’d be no reason for Bulger to kill him.” Bulger detractors suspect otherwise. Asked by People if suicide was a possibility, Rakes’s ex-wife Julie Dammers, who is planning his funeral, responded, “Absolutely not.”

Davis is determined not to let the unexplained death distract him from what’s unfolding inside the courthouse. With Bulger on the lam for 16 years until his arrest in 2011, it had once been hard to imagine anyone answering for the death of Davis’s petite sister. “The brutality of it haunts me to this day,” he says. “She was 18 months older than me and my best friend.” Now, as he attends the trial each day, Davis thinks Bulger a “coward” for refusing to make eye contact with him. “But I’m not there to see someone’s face,” he says. “I’m there to see justice.” And for that, he says, “I have waited a long time.”