Ex-prosecutor's loyalties in question

Flemmi, Bulger protector criticized

After taking over as chief of the New England Organized Crime Strike Force in the late 1970s, federal prosecutor Jeremiah T. O'Sullivan built his reputation on a single-minded pursuit of the Mafia and blunt, straight talk.

"I wish good luck - for me," Boston Mafia underboss Gennaro Angiulo once taunted O'Sullivan, in Italian, in court.

"You'll need it," the steely-eyed prosecutor snapped back.

Even two decades later, few question O'Sullivan's commitment to fighting the Italian mob. Yet now, as more attention is drawn to his role helping the FBI shield gangsters James "Whitey" Bulger and his sidekick Stephen Flemmi from prosecution so they could continue informing on the Mafia, some in law enforcement who once saw O'Sullivan's determination now see only duplicity.

"O'Sullivan created the impression that we were all in the same big boat," a former federal agent said recently. "You didn't realize until much later that you were really out in a life raft somewhere."

His role as an early protector of Bulger and Flemmi was on display again a few days ago, when Anthony "Fat Tony" Ciulla - the star witness in a 1979 horse-race-fixing case in which Bulger and Flemmi were implicated but never charged - blamed O'Sullivan and the FBI for allowing Bulger and Flemmi to remain free to commit crimes, including murder.

In the race-fixing case, O'Sullivan acceded to the wishes of Bulger's and Flemmi's FBI handlers, John Connolly and John Morris, and kept Bulger and Flemmi out of the indictment, which targeted the rest of their Winter Hill Gang.

O'Sullivan's name came up often during the court hearings in 1998 that first exposed the FBI's tight ties to Bulger and Flemmi, but he has never been heard from publicly on the issue. Just before he was to testify in federal court, O'Sullivan suffered a heart attack and a stroke. An independent doctor hired by the court found in late 1998 that the former prosecutor had suffered mental and physical injuries and warned that subjecting him to the stress of the witness stand could further endanger his health. The hearings concluded before he was deemed well enough to testify.

Now, 15 months later, O'Sullivan has recovered sufficiently to return to a reduced workload at the Boston law firm of Choate Hall & Stewart, although friends say he still has some motor impairment and is sometimes forgetful.

But he still refuses to talk about the actions he took more than two decades ago.

"The decisions I made while I was a prosecutor will not be debated on the front page of the newspaper," he said.

O'Sullivan's co-prosecutor in the race-fixing case, Richard Gregorie, agreed with Ciulla that there was enough evidence to prosecute Bulger and Flemmi, saying they "certainly" could have been indicted if the FBI had not pressured O'Sullivan to keep them out of the case so they could continue informing on the Angiulos.

"It was a battle and the bureau won," said Gregorie, now a federal prosecutor in Miami. "Jerry felt that the main goal [prosecuting the Mafia] was most important."

It was, in Gregorie's view, a legitimate call by a prosecutor. Gregorie said he would have done the same thing.

"You can't reach the high level of criminal activity without sources," Gregorie said.

Some former colleagues continue to defend the Faustian bargain O'Sullivan made with Flemmi and Bulger. "He is a very honorable guy who tried to do the right thing," said Martin Boudreau, a Boston lawyer and former Strike Force colleague. But others take a different view.

Among the harshest critics are those who saw their investigations stymied or undercut by the FBI and its loyalty to Bulger and Flemmi.

One ex-State Police organized crime investigator remembers a meeting with O'Sullivan and the FBI before a planned bugging of Bulger and Flemmi's West End headquarters, Lancaster Street Garage.

O'Sullivan reportedly told them that the FBI needed the troopers' surveillance photos, because "they didn't know all the players."

"In reality, it was all [expletive]," the investigator said. "The meeting was just for us to show them [the FBI] how much we had. O'Sullivan duped us."

The bugging ultimately failed. Bulger and Flemmi stopped meeting there once the bug was installed. Flemmi testified that they were tipped off to the bug by Morris, Connolly, and O'Sullivan, although US District Judge Mark L. Wolf ruled that Flemmi's testimony about O'Sullivan was not credible.

The detectives who investigated the 1982 murder of Tulsa, Okla., businessman Roger Wheeler are also among those who wonder whether O'Sullivan was willing to pay too high a price to bring down the Mafia.

In the summer of 1982 a team of investigators from Connecticut, Oklahoma, and Massachusetts went to O'Sullivan to talk about Brian Halloran, a recently murdered gangster who they believed might be connected to the Wheeler murder.

Former Connecticut State Police trooper Daniel Twomey remembers that, at first, O'Sullivan seemed to have extremely helpful information. The prosecutor said he had learned "third-hand" that Halloran had been asked by the Winter Hill Gang to kill Wheeler but had refused.

A little later in the meeting, O'Sullivan's account changed, Twomey said, and he admitted that Halloran himself had implicated Winter Hill, specifically Bulger, Flemmi, and an associate, John Martorano. But O'Sullivan downplayed Halloran's claim, insisting it was "not corroborated."

O'Sullivan said he had rejected Halloran's bid for federal witness protection because he did not believe him. O'Sullivan never mentioned that Bulger and Flemmi were FBI informants.

The detectives left the meeting not knowing whether Halloran's story about Bulger, Flemmi, and Martorano was a hot lead or another dead end.

Only years later did they learn that Bulger and Flemmi were subjects of a secret, FBI probe into both the Wheeler and Halloran murders that cleared them both - even though each had refused to take a lie detector test.

Martorano, now a government witness, reportedly admitted to the Wheeler killing last year and has implicated Bulger and Flemmi. Most of Halloran's account, he said, is true.

O'Sullivan's unwillingness to share all that he knew has left Twomey and the others wondering what could have been.

"That information might have been of some use," Twomey said. "You like to think that the people you work with are straight up with you."