Black Mass: Whitey Bulger, the FBI, and a Devil's Deal by Lehr, Dick, O'Neill, Gerard (2012)

PART ONE

The Prince of Darkness is a gentleman.

WILLIAM SHAKESPEARE (ACT III, SCENE 4),
KING LEAR

CHAPTER THREE

Hard Ball

As District Attorney William Delahunt was getting into his car to drive to a restaurant near his Dedham office, Whitey Bulger and two associates were barreling down the Southeast Expressway toward the same destination just outside Boston’s city limits. Delahunt was meeting another prosecutor for dinner. The mobsters were planning to terrorize the restaurant’s owner, who had stiffed them on a $175,000 debt. In one of life’s strange split screens, each party would do its business on a different side of the same big room in the Back Side Restaurant.

It was 1976, and the thirty-five-year-old Delahunt had been Norfolk County district attorney for only a year—just a little longer than Whitey Bulger had been teamed up with John Connolly and the Boston office of the FBI. But the chance encounter was not the only thing the DA and the gangsters had in common. One of the mobsters in Bulger’s crew, Johnny Martorano, had been a grammar school classmate and schoolyard rival of Delahunt’s. They had even been altar boys together.

When Delahunt looked up from a table near the bar, he recognized the Winter Hill hitman immediately. Martorano ambled over and sat down while the other two gangsters hung back. The former school chums shared a drink and got to jiving each other about their opposite lots in life. Johnny Martorano jabbed Billy Delahunt about there being more honor in his world than in the one populated by bankers and lawyers. Delahunt just chortled and did not argue the point with him. But when it was Delahunt’s turn to dish it out, he touched a nerve. Delahunt urged his old classmate-turned-gangster to stay out of Norfolk County. Stick to Boston, “for both our sakes,” Delahunt cautioned.

Martorano told Delahunt to pound sand, and the repartee got animated enough that one of Martorano’s companions joined them at the table to see what was going on. Bulger hung back, waiting by the entrance and out of sight, but Delahunt certainly recognized Martorano’s companion Stevie Flemmi. Then the odd encounter ended suddenly, and amicably enough, when Delahunt’s dinner companion, federal prosecutor Martin Boudreau, arrived at the table. When they were alone, Delahunt rolled his eyes and said, “You’ll never guess who I was talking to.”

Meanwhile, Bulger joined Martorano and Flemmi, and the threesome picked a cocktail table against the back wall and set up there. Arms folded, they sat waiting for the owner to appear. They had come to see Francis Green because he had some explaining to do.

About a year earlier Green had borrowed $175,000 from a high-interest Boston finance company for a real estate investment. The problem was that Green had not paid back a dime and, though he didn’t know it, was stiffing a friend of Winter Hill’s. Whitey knew a way to solve such bad debts. It was not genteel.

Green came into the large central room, spotted the three gangsters, and slid into an empty seat. As was his wont, Bulger skipped the small talk. “Where’s our money?” he asked. Green, a glib salesman with a checkered past, tried a salesman’s tap dance. His finances were in shambles. His business deals had gone bad. He was in bad shape. This had to count for something.

But Bulger would have none of it. No money is no answer. It didn’t matter that two prosecutors were seated across the way. Bulger leaned into Green’s face, his eyes cold marbles. “Understand this,” Bulger told him, “If you don’t pay, I will absolutely kill you. I will cut off your ears and stuff them in your mouth. I will gouge your eyes out.”

Then Bulger leaned back. He told Green he really should make an appointment with his loan officer to arrange a schedule for repayment. And Flemmi, playing the good cop to Bulger’s tough cop, advised Green to pay something real soon. That way, comforted Flemmi, no one would get hurt. Then it went back to Bulger, who made one final chilly comment: make it $25,000 within a few days.

An ashen Green said he would see what he could do. The brisk business meeting was over. An FBI report afterward recorded in leaden government prose that the conversation “greatly upset” Green. It was an understatement. Green was in fear for his life, and it was fear mixed with bewilderment. He was aware that Martorano and Delahunt had earlier been mingling at the bar, and the entire scene that night left him confused about what exactly he was up against.

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, 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 also 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 US 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 recreated 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 walk the case over to the FBI office personally 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 close the case officially 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 that pattern 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 and 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?

Five years would go by before some answers began to crystallize for Delahunt. Over time his office’s relations with the Boston FBI would sour. Tensions between different police agencies and different prosecutors’ offices were not uncommon. It came with the turf, in Boston or in any jurisdiction. But this was different.

First came a sensational murder case that Delahunt’s office got involved with not long after the Green matter was turned over to the FBI in early 1977. To solve the murder case and locate the bodies of two eighteen-year-old women from Quincy, Delahunt and his state police investigators cut a deal with an informant by the name of Myles Connor. Connor was a vicious con man who had a high IQ and a long history of trouble. He was a rock musician and an accomplished art thief and drug dealer. His past included a 1966 shootout with a state trooper who was badly injured. Even in the venal world of informants, Connor was a mixed bag of trouble. But he knew where the bodies were buried.

Nonetheless, cutting a deal with Connor was controversial, both inside Delahunt’s office and beyond. The FBI was enraged because Delahunt, to win Connor’s help, had negotiated his early release from prison. Even though with Connor’s help Delahunt would find the bodies of the missing women and then convict the murderer at a trial in 1978, the FBI angrily challenged the district attorney’s unholy alliance. It was the FBI that had put Connor behind bars on a stolen art conviction. FBI agent John Connolly himself began urging the US attorney to investigate what role, if any, Connor had in the grisly murders. Eventually Connor was charged with planning the killings. He went to trial and was convicted, an outcome that was overturned on appeal. During the subsequent retrial Connor was acquitted.

Delahunt had known that cutting a deal with Connor would prove controversial. Key staff in his own office, whose judgment he relied on daily, had told him as much. But he’d had no idea the situation would explode into the open warfare that followed, with angry exchanges in courtrooms, in the newspapers, and on television as well as in more sinister ways that would have seemed unimaginable at the start.

Some of the warfare got personal. One day John Connolly contacted one of Delahunt’s top assistants, John Kivlan. The young prosecutor was known to have had reservations about using Connor as an informant. Connolly called Kivlan and set up a lunch date. Kivlan showed up thinking the FBI agent wanted to discuss another murder investigation. But quickly Connolly began asking a lot of questions about Delahunt and the deal he’d cut with Connor. The FBI agent was especially curious to know if Delahunt and the state police had believed that Connor was guilty of the murders but had given him a pass anyway to bask in the glory and publicity that came with recovering the bodies.

“It wasn’t long,” Kivlan said later, “before I realized the lunch was about getting some dirt on Bill.”

Kivlan was taken aback by Connolly’s overture. “I thought to myself, ‘He must think everyone is an informer,’” Kivlan recalled. “I guess he thought my concerns would amount to trading information with him. It was a short lunch.”

Looking back, and long after telling Delahunt about the bizarre encounter with Connolly, Kivlan would wonder if the rabid battle between Delahunt’s office and Connolly’s FBI was less about Connor and more about Bulger. In any case, when Connolly could have been busy fighting crime, he was spending much of his time in a down-and-dirty public relations battle. In fact, crime fighting was becoming less of a clear-cut priority for the young agent from South Boston.

▪   ▪   ▪

Delahunt had limped away from the bruising encounter with the FBI over using Myles Connor as an informant, chewed up in the FBI public relations maw. Federal officials publicly chided him for using an informant who was involved in the kinds of crimes he was giving information about. By and large the media sided with the FBI, mostly on the strength of John Connolly’s personal ties with reporters at the Boston Globe and the Boston Herald and with some television reporters. Indeed, Connolly was fast becoming a public relations maven and a talented improviser with the truth. Garrulous and engaging, he was breaking free of the grim, button-down G-man persona, a welcome change from the aloof, stone-faced demeanor of most federal agents. Connolly not only occasionally talked to reporters but also regularly courted them.

But this was early on, and there were only a few within law enforcement who suspected the FBI was tilting Bulger’s way. Delahunt was one of them, but he had learned there was a price to pay for confronting the Boston FBI. It was hardball. And being Boston, it was personal.

In 1980 a rumor took hold that Delahunt had had an affair with a waitress from Quincy that ended badly, with a door broken at her apartment and raised voices overheard by neighbors. The media heard about it, and one television reporter began calling the woman. The calls continued for the next two years, and each time the woman was urged to take Delahunt to court and go on air for an interview. But each time the woman said there was no case, that there was nothing to the rumor, “not a speck of truth.” If any of it were true, she said, “Delahunt would not be DA today, believe me.”

But the media weren’t the only parties interested in the rumors. Two FBI agents showed up at the restaurant in Quincy one day in late 1982 asking for the waitress. The chef told the agents she didn’t work there anymore. The agents took down some notes, thanked the chef, and left. They never called again.

Then there was the call the woman got in January 1983. It was from a man in her past. She later described the old friend to local police as “someone on the other side.”

The two met for a drink in a Quincy lounge. The friend, Stevie Flemmi, shocked the woman by knowing about the Delahunt rumor. Flemmi really just wanted to know one thing: was it true?

No, it wasn’t, the woman said one more time. Stevie never called again either.