Whitey Bulger trial reveals sordid gang underworld in shocking detail

The testimony of Stephen Flemmi Tuesday in the James 'Whitey' Bulger case marked some of the most sordid moments in a trial filled with them as the defense sought to discredit Bulger's former associate.

J. Pat Carter and US Marshals Service/AP/File
This pair of file photos shows Stephen 'The Rifleman' Flemmi (l.) in 2008 and James 'Whitey' Bulger (r.) in 2011.

The defense team for crime boss James “Whitey” Bulger sought to undermine the credibility of a key witness during cross-examination Tuesday, portraying him as prone to lying and killing – thus raising the possibility of a frame-up job against Mr. Bulger.

The federal lawsuit alleges that Bulger’s crimes include 19 murders, with witness Stephen "The Rifleman" Flemmi stating that he witnessed him strangling two women in the 1980s.

Attorney Hank Brennan was blunt with his line of attack, suggesting to Mr. Flemmi – a former Bulger crime partner – that “[you are] good at misleading people, aren't you?”

Flemmi said deception often goes with the territory of a criminal enterprise.

“Were you excellent at misleading people?” Mr. Brennan followed up.

Flemmi was able to avoid answering that question, as Judge Denise Casper sustained a prosecutor’s objection.

But the exchange encapsulates a marathon day of verbal dueling between a skilled lawyer and an assertive witness, which also gave the judge plenty of work to do as moderator.

Bulger has made little effort to defend himself against many of the charges, but he is fighting particularly hard to be exonerated in the deaths of two women: Debra Davis (a Flemmi girlfriend) and Deborah Hussey (a Flemmi stepdaughter). His lawyer's attempt to put Flemmi on the defensive regarding Bulger's alleged role in those two deaths resulted in some of the most sordid moments of a trial that has been full of them – including accusations of pedophilia and testimony that Flemmi took his stepdaughter to the mall before delivering her to Bulger to be killed.

A challenge for the defense is that another witness at the trial, Kevin Weeks, has said he witnessed Bulger’s involvement in the strangling death of Ms. Hussey. When Mr. Weeks was under indictment, he also led investigators to the site where she and two other murder victims were buried.

Bulger’s defense argues that key witnesses against Bulger – Flemmi and Weeks included – have gotten lighter sentences in exchange for their willingness to testify against Bulger or against corrupt FBI agents with ties to his criminal gang.

For his part, Flemmi appeared conversational and sometimes combative, more than rattled at the defense's questioning. The drumbeat of defense questioning has already lasted several hours and is scheduled to continue Wednesday.

By trying to erode Flemmi’s credibility, the defense is aiming to keep jurors from being persuaded “beyond a reasonable doubt” about Bulger’s guilt.

Regarding Flemmi as a liar, Brennan got Flemmi to talk about how he deceived Ms. Davis’s family, claiming to not know her whereabouts after she disappeared.

Regarding Flemmi as a killer, Brennan got him to talk about several murders that occurred before Flemmi became closely involved with Bulger.

Flemmi has said the motive in the slaying of both Davis and Hussey was because they knew too much about Bulger group’s criminal activities and couldn't be trusted to stay silent.

Brennan implied that Flemmi had another motive, jealousy, when Davis died shortly after Flemmi learned that she was interested in another man.

The question of pedophilia came up due to Flemmi’s acknowledgment that he engaged in sexual acts with Hussey when she was a teenager. Flemmi sought to turn the tables, embellishing an answer by saying that Bulger also was interested in young girls – taking a 16-year-old on a vacation to Mexico once.

While the day of questioning covered some of the more unsavory topics in the trial, it also had at least one moment of levity, when Flemmi described fixing a car used by FBI agents who had a corrupt relationship with him. Flemmi said the car was into his gang’s garage by 9 a.m. and was “out and ready by 4.”

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