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Whitey Bulger to face 'The Rifleman,' his right-hand man, in court

Stephen 'The Rifleman' Flemmi is expected to testify in the James 'Whitey' Bulger case Thursday. As Bulger's former partner in crime, Flemmi could be crucial to the prosecution.

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Stephen 'The Rifleman' Flemmi, a jailed Boston mob leader, testifies in a Miami courtroom in the murder trial of former FBI agent John Connolly in this 2008 file photo. He is expected to testify in the 'Whitey' Bulger case this week.

J. Pat Carter/AP/File

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The trial of Boston crime boss James "Whitey" Bulger is nearing a pivotal moment, as the prosecution tries to cement its case by calling his former partner to testify.

Stephen "The Rifelman" Flemmi is expected to take the witness stand Thursday and to say that he and Mr. Bulger cooperated in killings that included two women.

Bulger was captured in 2011 after a 16-year manhunt. Federal prosecutors say Bulger ran an organized-crime outfit with Mr. Flemmi that was responsible for extortion and at least 19 murders. Flemmi, who is serving a life prison sentence after admitting to 10 murders, is central to their case.

Although Bulger has pleaded not guilty, his defense lawyers have acknowledged that their client was deeply involved in criminal activities such as gambling and loan sharking. But the defense attorneys are seeking 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, according to news reports, is to cast doubt on the notion that he served as an FBI informant or that he killed women.

Flemmi’s testimony promises to go to the heart of both issues.

A 700-page FBI file documenting Bulger as an informant is based on numerous meetings between Flemmi, Bulger, and FBI Agent John Connolly, prosecutors say. Bulger’s attorneys say, rather, that their client was paying Mr. Connolly for information and protection, not giving the FBI tips.

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