Whitey Bulger trial: 'Rifleman' Flemmi details murder after grisly murder

In matter-of-fact tones that made him appear completely unmoved at recalling the many violent deaths he admits causing or helping plan, Stephen “the Rifleman” Flemmi on Friday detailed murder after grisly murder committed alongside defendant James “Whitey” Bulger.

Mr. Flemmi’s graphic testimony at the federal courthouse in Boston may be the most important part of the case for prosecutors who are trying to provide the jury with chapter-and-verse insider testimony to nail shut each of the 32 racketeering charges, including 19 murders, against Mr. Bulger. Flemmi detailed about half of those murders Friday – with his testimony expected to continue next week.

Bulger and Flemmi ran the South-Boston-based Winter Hill Gang for more than 20 years, making millions by extorting bookies, loan sharks, and drug dealers, prosecutors say. But the pair also planned – and mopped up after – the killing of mob figures, businessmen, potential informants or “rats” – including even Flemmi’s own girlfriend, Debra Davis.

Bulger strangled Ms. Davis in 1981 “because I couldn’t do it – and he knew it,” Flemmi testified.

Even so, Flemmi said he put aside his feelings “and did what I had to do,” and cleaned up after the murder. This included, he said, removing Davis’s clothes so there would be fewer identifying elements, wrapping her body in a plastic tarp, and hauling it away in the trunk of a car to bury near a highway in Quincy, Mass.

With a federal indictment bearing down on the pair in 1994, Bulger fled Boston and lived on the run for 16 years before being caught, while his former partner Flemmi was arrested and eventually confessed to 10 murders – escaping the death penalty through a deal with prosecutors.

Although Bulger has pleaded not guilty, his defense lawyers have already acknowledged their client was deeply involved in criminal activities such as gambling and loan sharking. But the defense wants to cast doubt on the credibility of key prosecution witnesses – including Flemmi and other former criminals who received lighter sentences in return for their willingness to testify.

Topping Bulger’s wish list, say observers, is having his defense team and witnesses cast doubt on the whole idea that he ever served as an FBI informant or that he killed women.

Prosecutors began Friday by immediately quizzing Flemmi about the early days of his life of crime in the 1960s. What emerged were details of killings needed to underpin and enforce the highly lucrative crime operation in South Boston.

Under questioning from Assistant US Attorney Fred Wyshak, Flemmi first detailed how he came to be associated with the Winter Hill crime gang ­­– and how he came to be friends with Bulger.

Along the way, Flemmi was peppered with questions about various victims – who they were, what they did – thus detailing a string of murders he had either witnessed, planned, assisted with, or carried out on his own – most committed in the company of Bulger.

Flemmi recounted, for instance, meetings of the Winter Hill gang where Bulger insisted that certain individuals should be killed. When there was gang agreement, he testified that he then helped carry out the hits.

Flemmi recalled travelling to a shooting range in Hopkinton, Mass., ostensibly to show friends how to shoot. But he also had a body with him that he later helped bury at the remote site.

Flemmi also detailed how Bulger came to introduce him to FBI agent John Connolly in 1975 – and how inside information from Connolly, relayed by Bulger, helped them several times avoid being entrapped by sting operations.

Bulger, he said, told his associates that it was important to meet with Mr. Connolly.

“The Mafia has their sources and we can help you,” Bulger quoted Connolly as saying, Flemmi testified. “If they want to play checkers, we can play chess,” Bulger told the gang, Flemmi said.

One of those stings was a loan-sharking operation that was being videotaped by the FBI. But Connolly’s warning, relayed through Bulger, enabled Flemmi to avoid the location and avoid arrest. As a result, he felt “grateful,” he said, which was one reason he was willing later – at Bulger’s insistence – to meet directly with Connolly.

Flemmi testified that he always assumed that inside information he was getting from his own contacts inside the Mafia, and then gave to Bulger, was then being relayed by Bulger to Connolly. It was that information the FBI was using to try to shut down Mafia operations in Boston, according to later reports.

Undercutting Bulger’s contention that he was never a “rat,” Flemmi said he witnessed Bulger tell Connolly at meetings “hundreds of times” about an array of criminal activity. It was a point addressed in his first day of testimony.

"Who did most of the talking at these meetings?" Mr. Wyshak asked Thursday.

"James Bulger," Flemmi replied.

He was then asked to describe his relationship with Bulger.

"Strictly criminal," he replied.

Flemmi also testified that Bulger told him he had murdered Paul McGonagle, a Boston mobster. His testimony backs up that of John Martorano, a hit man who detailed Bulger's involvement in several  murders.

In his account, Flemmi told how both Bulger and Flemmi had fired their weapons at Eddie Connors, a bar owner who had bragged too much about his own role helping the gang in one of the murders. Connors was shot multiple times in a phone booth.

All the testimony about blood and betrayal and informing from prosecution witnesses is about building an iron box that Bulger’s lawyers won’t be able to break out of when they begin calling defense witnesses, legal analysts say.

“It’s been a slow, tedious, but workmanlike performance by prosecutors that’s necessary to establish the scope of charges that cover nearly 30 years,” says Michael Coyne, associate dean at the Massachusetts School of Law, who has followed the trial closely. “Flemmi, being with Bulger most of the time, provides the jury with details needed to prove the facts alleged in the indictment.”

Flemmi’s testimony Friday also corroborated that of Kevin Weeks, another Bulger associate, who previously testified that Bulger’s gang was extensively involved in drug dealing in South Boston – another area that Bulger has denied involvement, Mr. Coyne notes.

“Did you earn money from that?” prosecutor Wyshak asked, regarding the drug-dealing business in South Boston.

“A substantial amount of money over time,” Flemmi responded.

“Who operated the drug dealing,” Wyshak probed.

“Jim Bulger organized the whole thing,” Flemmi said.

Bulger still faces the prospect of other multiple indictments in Florida and Oklahoma for crimes committed there. That, Coyne notes, leaves him one objective from the current trial – to preserve a reputation he felt he once had in his hometown of South Boston as a sort of Robin Hood. To do that, Bulger needs to create the plausibility that he was neither a drug dealer nor murderer of women and, most of all, not a “rat.”

“No matter what happens in this court here, he will never see the light of day – and he knows it,” Coyne says. “Now it’s all about his personal code – he’s now trying to preserve his personal legacy and image. That’s what it’s been about from Day 1.”