BOSTON — The longtime girlfriend of former Boston crime boss James “Whitey” Bulger was by his side when he was finally captured in Santa Monica last month after more than 16 years on the run.

Next week, prosecutors are expected to argue that Catherine Greig’s years on the lam with one of the nation’s most wanted fugitives make her a flight risk if she is released on bail.

But some legal analysts say Greig has a chance of being released if her lawyer can find a way to separate her conduct from Bulger’s.

Bulger, now 81, the former leader of the notorious Winter Hill Gang, is charged with participating in 19 murders and a host of other crimes, including loan-sharking and money-laundering. He faces the possibility of life in prison.

Greig, 60, is charged with harboring a fugitive, which carries a maximum prison term of five years.

“Just because there might be a legitimate argument that Whitey would obstruct justice and flee if he were let out (on bail) doesn’t mean that his girlfriend will,” said Chris Dearborn, a professor at Suffolk University Law School.

“They need to be treated individually on the question of whether bail is appropriate,” he said.

Greig is due in U.S. District Court for a bail hearing Monday.

Defense attorney Edward Ryan Jr., a former president of the Massachusetts Bar Association, said some of the main arguments prosecutors make against releasing a defendant on bail do not seem to apply in Greig’s case. Unlike Bulger, who is charged with violent crimes, Greig is not considered a danger to the community or someone who would attempt to obstruct justice or threaten witnesses if she were to be released on bail, Ryan said.

Ryan said a magistrate could release Greig on bail, but require her to wear an electronic monitoring bracelet and establish other conditions to keep close track of her.

“The purpose of bail is to ensure the person’s return to court,” said Ryan. “The magistrate will have to determine if there is a set of conditions that will basically ensure her return to court, and I think you can do that here.”

But prosecutors made it clear at Greig’s initial court appearance they intend to argue that she would be a flight risk if she is released while awaiting trial.

“The fact that she was living with and harboring a fugitive for all those years is obviously going to weigh heavily against having her released,” said former U.S. Attorney Donald Stern.

“I think the government has the better argument, but I don’t think it’s necessarily a sure thing that the government will prevail here,” he said.

Authorities say Greig, a former dental hygienist, went on the run with Bulger shortly after he fled in late 1994. Bulger disappeared after he was tipped off by a former Boston FBI agent that he was about to be charged in another case that has since been dismissed.

Bulger and Greig were caught on June 22, just days after the FBI began a new publicity campaign focusing on Greig.

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