Black Mass

It was all pretty bizarre, the kind of odd occurrence that comes with life in and around a big small city like Boston. For their part, the two prosecutors were oblivious to the extortion nearby. Over at their table, Delahunt and Boudreau joked during dinner about winding up at the same restaurant with Martorano and Flemmi of the Winter Hill gang. They hadn’t realized that the third man in the entrance shadows was the notorious Whitey Bulger. But Delahunt had no idea at the time that the business activity at the cocktail table was actually a prelude to the bad relations to come between the rest of law enforcement and the Boston office of the FBI. In the future it would seem like the world was divided between the FBI and Bulger, on the one hand, and all the other police agencies on the other. At the moment, though, the chance meeting just seemed to be one of those crazy things that happen but don’t really mean anything.

The Bulger ultimatum—pay or die—quickly sent Green scrambling to seek out his own contacts in Boston’s law enforcement community. He started with Edward Harrington, who was the former chief prosecutor at the federal Organized Crime Strike Force for New England. Green not only had had some dealings with the strike force over the years but had raised money for Harrington’s unsuccessful run for state attorney general in 1974. Harrington was about to rejoin the ranks of government service as the new U.S. attorney in Massachusetts, but he was in private practice at a law firm when Francis Green came calling in full panic.

Green wanted Harrington’s counsel. What should he do? Harrington, according to an FBI report, was blunt. He told Green he had three options: Pay the money. Get out of town. Or testify against Bulger.

Green took stock of the situation. Repayment was out of the question. He had squandered the money. Relocation was not appealing. Testifying against the reputed killer seemed even worse. But it was this last option, the one that perhaps carried the highest risk, at least to life and limb, that Green began to contemplate.

In the weeks that followed Green asked Harrington more questions about cooperating, and Harrington decided that because the extortion occurred in Norfolk County, the matter could best be pursued through a state investigation. He told Green that the case should be developed out of District Attorney Delahunt’s office. But what about Delahunt? Green was worried about Delahunt’s ties to Martorano. He had seen the two men sitting there at the Back Side Restaurant sharing a drink and having a laugh.

Harrington phoned Delahunt and briefed him about Green and Bulger’s threat. Then he mentioned Green’s concern about the county prosecutor bantering with Martorano. Delahunt assured Harrington that it was only a chance meeting, that there was nothing between the two men beyond faded boyhood memories. Arrangements were made for Green to take his evidence to Norfolk County prosecutors.

Soon afterward Green met with Delahunt and his top staff. In gripping detail, Green re-created the dramatic night at the Back Side. The story stunned Delahunt. He’d had no idea that this conversation was happening just out of earshot of his dinner with Boudreau.

Later Delahunt huddled with his staff. Green’s story was explosive, and Delahunt was personally involved. He had, after all, been in the restaurant that same night and could provide eyewitness corroboration that Martorano and Flemmi were present. Could he be both witness and prosecutor? Unlikely. Plus, the county prosecutors wondered if Harrington had been wrong to conclude that this kind of case should be pursued at the state level. They knew that federal extortion laws carried stiffer penalties than they could ever hope to win under Massachusetts law. So Delahunt consulted with Boudreau, the federal strike force prosecutor and law school classmate he’d dined with that night at the Back Side, who agreed with Delahunt’s analysis. He even offered to personally walk the case over to the FBI office to get the ball rolling. With Delahunt’s approval, the case was forwarded to the FBI.

JOHN CONNOLLY was worried. Green was the first big bend in the Whitey Bulger highway. But priorities were priorities, so Connolly quickly set out to ensure that the case would never leave the Organized Crime Squad where he worked.

Two agents from the squad did some perfunctory poking around. The agents, both of whom worked side by side with Connolly in the close-knit squad, interviewed Francis Green. They even visited Delahunt and wrote down what he knew.

Then they wrote up a report and put it in the FBI files. And that was the end of it. In about a year the agents asked their boss for permission to officially close the case against Bulger, noting that Green was reluctant to testify against him. Local prosecutors had heard that Connolly had conducted an interview in the case and asked for a copy of his report, but the FBI denied it had taken place and said there was no paperwork.

In the years to come a similar pattern would emerge about witness “reluctance.” Time and again John Connolly and his colleagues would talk to a potential witness against Bulger and come back to the office and throw up their hands—the once promising person was now reluctant to cooperate. Or reluctant to testify. Or reluctant to wear a wire. And what was an agent supposed to do if the witness was so reluctant? Time and again leads went nowhere, and it was a pattern that began with Francis Green’s “reluctance.” Eventually Green would testify for federal prosecutors in an unrelated public corruption case, but no one ever contrasted his willingness in that case to his reluctance in the Bulger matter. Instead, once inside the FBI the extortion case had found its way to the back of a file cabinet. It would be the first of many.

GIVEN the fast pace and short memory of law enforcement, the Green case drifted unnoticed into limbo. Bulger backed off Green because of the heat, while Delahunt assumed that the FBI was pursuing the issue. It would be months before the district attorney realized that nothing had been done on an easily made case.

About a year after the initial contact, Delahunt ran into the top federal prosecutor, Jeremiah T. O’Sullivan, at a social function. Whatever happened with that Green thing? Delahunt asked him. “We checked it out, but there was nothing there,” he told Delahunt.

Delahunt shrugged and thought, Okay, that happens. “And I meant it,” Delahunt said later. “Cases don’t work out.”

But this one gnawed at him because, every time he thought about it, things didn’t compute. A district attorney as a witness who could put notorious gangsters at the scene. An owner’s compelling testimony. Why hadn’t the FBI picked up the ball and run hard with it against the infamous Bulger and Flemmi?