BOSTON — James "Whitey" Bulger's flight back from Los Angeles to Boston on Friday was only the beginning of a much longer journey, a legal odyssey that is likely to keep him in court for years. Unless Bulger, who is 81, bypasses the long court process with plea deals, the trials themselves could be a death sentence.
When Bulger dropped out of sight in 1995, he became one of the nation's most notorious fugitives, under indictment for racketeering in connection with accusations of extortion, money laundering and 19 killings.
The bulk of the prosecution will take place in Boston, where Bulger faces two indictments, each weighing in at about 100 pages. But other prosecutions await over killings in Miami and in Tulsa, Okla., where state charges could involve the death penalty. The process of determining which cases move forward first and how they will be conducted will be the subject of coming negotiations among state and federal law enforcement agencies in three states.
The criminal complaint against Catherine Greig, Bulger's 60-year-old girlfriend, is far less complicated; it is just 11 pages, including an FBI agent's affidavit. It charges that Greig "did harbor and conceal" Bulger since Jan. 5, 1995.
The complexity of Bulger's prosecutions will be enormous, but the various offices are accustomed to such negotiations, said Susan Witt, a spokeswoman for Tim Harris, the Tulsa County district attorney. The offices have gained valuable coordination experience in prosecutions of members of Bulger's Winter Hill Gang, Stephen Flemmi and John Martorano, Witt said.
First, however, Bulger will have to get a lawyer, said Martin G. Weinberg, a defense lawyer in Boston, and "his challenge is how to manage a defense with this complexity of allegations that are at the gravest levels of potential penalty." A more immediate issue, Weinberg suggested, is "How does the defendant in this position develop a defense team?"
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Bulger has been a fugitive for 16 years, and any assets — including $800,000 taken from his Santa Monica, Calif., apartment — could be subject to forfeiture. In a brief court appearance in Boston on Friday, Bulger asked the court to appoint a lawyer because the government had seized his money.
"We think he has access to more cash," said prosecutor Brian Kelly.
At a second hearing, Bulger took a swipe at prosecutors after Magistrate Judge Marianne Bowler asked him if he could afford to pay for an attorney.
"Well, I could, if they would give me my money back," he replied in his unmistakable Boston accent, prompting laughter in the courtroom.
Kelly implied that Bulger's cash came from illegal activities.
"He clearly didn't make that on a paper route on Santa Monica Boulevard," he said.
Kelly also said Greig told court officials that Bulger's brother may be willing to assist him in posting bail. The amount of money found in Bulger's apartment confirmed a longheld belief by investigators that he kept large stashes of cash for a life on the run.
"We clearly don't think this is his last stash," Kelly said.
When Bulger walked into the courtroom, he saw his brother William seated in the second row. Whitey Bulger smiled at him and mouthed, "Hi." His brother smiled back.
William Bulger was once one of Massachusetts' most powerful politicians. What the former state Senate president and, later, president of the University of Massachusetts knew about his brother's activities — and whereabouts all these years — has long been a matter of speculation and investigation. Public pressure eventually cost him his university job in 2003.
Asked after the brief hearing whether he would comment on his brother's arrest, Bulger said: "Perhaps later I'll make a statement. I'd like to think about it.''
He let out an exasperated laugh when asked whether he might post bail for his brother.
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A major question that could bedevil the case is what Bulger knows, and whether it could play a role in other investigations and cases. From 1975 until his disappearance, Bulger was an informer for the FBI, using his contacts with a Boston agent, John Connolly, to help the bureau go after the Italian mob in the city.
But Connolly was later found to have allowed Bulger and an associate — Flemmi — as well as others to continue criminal activities, to have protected them from prosecution and even to have told Bulger of his impending arrest in late 1994, prompting him to flee. Connolly was later convicted of racketeering for protecting Bulger and Flemmi.
Getting Bulger to talk — or the FBI to seek his help — might not be easy, said Gerald L. Shargel, a Manhattan lawyer who represented John J. Gotti, the late boss of the Gambino crime family in New York. Citing the mayhem and scandal associated with Bulger's career as an informant, he said, "I don't think the relationship between Bulger and the FBI is a happy one, and I don't think that Humpty could be put back together again."
Other experts suggested that interrogations would be a high priority, but with history in mind, the FBI might not be the only agency in the room. Brien T. O'Connor, a former prosecutor in Massachusetts now in private defense practice, said, "I don't doubt for a second the FBI's integrity in dealing with Whitey Bulger in 2011, but still there is the public confidence issue" from years past.
O'Connor said, "Just from the perspective of public confidence, my view is that the FBI ought to include others, for example the DEA and the State Police in Massachusetts who have worked very hard on the evidence and have continued in a very significant way to bring down a lot of these organized-crime figures from the '70s and the '80s'."
Bulger is said to have boasted that he corrupted six FBI agents and more than 20 police officers. If he decides to talk, some of them could rue the day he was caught.
"They are holding their breath, wondering what he could say," said Robert Fitzpatrick, the former second-in-command of the Boston FBI office.
In the late 1990s, U.S. District Judge Mark Wolf found that more than a dozen FBI agents had broken the law or violated FBI regulations. Among them was Connolly's former supervisor, John Morris, who admitted he took about $7,000 in bribes and a case of expensive wine from Bulger and Flemmi.
Information from the New York Times, Associated Press, Boston Globe and Los Angeles Times was included in this report.