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During their opening statements, Bulger's lawyers acknowledged he ran a lucrative criminal enterprise that took in millions through illegal gambling, extortion and drug trafficking.
Boston attorney Martin Weinberg said because Bulger's lawyers have admitted to some charges, he is likely to be convicted of enough counts to keep him in prison for the rest of his life.
"He's going to have a narrower set of objectives," Weinberg said.
"It makes it more likely for him to testify if his objectives are something other than a complete acquittal because he can admit to things that other defendants couldn't and attempt to persuade a jury that, 'You heard what I admitted to, please respect those specific areas as to which I deny guilt.'"
But Bulger runs a high risk of prosecutors bringing in more damaging evidence if he testifies.
"He might insist that he wasn't a rat, he wasn't an informant. ... But is it worth it for him to hold his head high and say, 'I wasn't an informant for the government, or I never killed women' when he will be forced to admit other things on the stand?" said Boston College law professor Michael Cassidy.
Ultimately, the decision will be up to Bulger.
Cassidy said Bulger could decide to testify simply to deny claims made by three once-loyal cohorts who became government witnesses and testified against him.
"He has to sit and listen to them without telling his version of the story," Cassidy said. "Maybe he just insists on (testifying). 'You know, I'm going to jail for the next 10 years anyway, I'm going to die in prison. At least I'm going to have my time on the stand.' That's his right."