Black Mass

Katz went off to prison in Pennsylvania. After he settled in and made a few friends, he was abruptly transferred to a spartan holding cell in Massachusetts. He was put in front of a grand jury to answer questions about rents. If he refused, it would mean eighteen more months in prison.

After a year in jail Katz rolled, deciding he did “wanna go with Chico” to the witness protection program after all. He became another key witness against Bulger and Flemmi.

JOE YERARDI was next up in the march toward Winter Hill. Going after Joey Y was cutting closer to the bone. Krantz and Katz paid to be left alone. But Yerardi was a leg-breaker who worked for Bulger and Flemmi, putting over $1 million of their money on the street and collecting their debts. Yerardi did run some bookies, but loan-sharking was his thing. And his criminal record was far different from the other customers at Heller’s. There were firearm violations and several assault and battery convictions in state court.

Yerardi’s main line of work had become handling usurious loans for the bad-to-the-bone Johnny Martorano. His formal ties with Flemmi and Martorano made him a prime target for Wyshak as he assembled his witness list. Yerardi knew that too. And so did Stevie and Whitey.

By the middle of 1993, with Krantz in hand and Katz up against it, the writing was on the wall. A grand jury was going strong, and indictments were in the air. Whitey pulled Stevie aside: time for a vacation. Stevie lit out for Canada, just as he had two decades earlier. Bulger took one of his slow drives across America with Theresa Stanley.

And Yerardi fled too, heading to Florida with $2,500 sent him by Martorano. But he made the mistake of using an old alias from Massachusetts, and six months after he was indicted the Massachusetts State Police found him living in Deerfield Beach as Louis Ferragamo. The fatalistic if bumbling Yerardi asked the troopers, “What took you so long?”

Joey Y became the Gordon Liddy of Heller’s Café. He continued making loan collections while under house arrest and never complained about the United States becoming Russia. He could have croaked Flemmi, with whom he had extensive dealings. In fact Stevie was on a tapped line talking business with Yerardi. But Yerardi stood up, taking an eleven-year sentence as the price of saying no to Wyshak, and law enforcement had to move forward with Chico and Katz and others who lined up at the cashier’s cage in Heller’s Café.

THE BOOKIE brigade had become the soft underbelly of the Bulger gang. It kept Whitey and Stevie on the firing range and shifted the prospect of indictments from the outlandish to the inevitable. And it left the FBI scrambling for a piece of the action, if only to avoid the embarrassment of sitting on the sidelines while a major case was made against the most renowned gangsters in Boston by the Massachusetts State Police. The bureau saw the train leaving and jumped on board at the end.

By the middle of 1994, with London and Yerardi in prison and all the Heller Café tapes deciphered, prosecutors began assembling the rest of the racketeering case that involved historical evidence from 98 Prince Street, Vanessa’s Italian Food Shop, and the 1989 mob induction. This required the FBI to designate someone to help round up the material, and that job fell to Edward Quinn, the hero of the Angiulo case who now headed the Organized Crime Squad.

Though Quinn commanded respect from other investigators, the intramural jockeying continued and showed itself in a spate of news stories, several from the FBI, that reported promising developments in the quest for Bulger. Stories with unnamed sources said, “It’s getting close to Bulger, but it’s not quite there.” The analysis could be read as a warning for Bulger to stay gone. And behind the news stories, John Connolly had been keeping Bulger and Flemmi updated on grand jury progress. In particular, they discussed the Yerardi investigation, which had veered toward Bulger’s gang.

THOUGH bookies were the mainstays in the percolating case, prosecutors also finally broke through the South Boston code of silence. In addition to Timothy Connolly’s testimony, there was the momentous flip of true believer Paul Moore, a skilled boxer and renowned street fighter whose nickname “Polecat” derived from his fast hands and feet. Moore had headed one of Bulger’s cocaine distribution networks and was the real deal, a genuinely tough guy who had pled guilty in the 1990 drug case. He went off to do nine years at a federal prison in Pennsylvania, tight-lipped but buoyed by expectations that were also part of the code—a good lawyer, family support, home insurance. But after a few years in prison he felt that his questions about an appeal were falling on deaf ears. His wife was not getting the support she needed. And a bank foreclosed on his home.

In 1995 Moore had the epiphany that comes to those sitting in a prison cell while other more deserving candidates are walking the streets back home. By this time he was hearing stage whispers from the prison network that Whitey was a rat. He began asking himself the rhetorical question that prosecutors count on: what am I, an asshole? The process accelerated when Moore was hauled before a grand jury and faced another year and a half in prison if he didn’t answer questions about Bulger. Breaking with Whitey the Rat was the easy part. The code was a different story. But Moore had had enough. He asked one thing: put me near the water so it will be as much like South Boston as a modest house and a small shoreline can make it. He entered the witness protection program as someone who would testify against Bulger.

AS THE doggedly determined prosecution moved forward, the strategy remained the same, even as the witness list was reshuffled. Katz and a half-dozen bookies replaced Krantz, who was diagnosed with the leukemia that eventually killed him. Paul Moore and loan officer Timothy Connolly replaced the adamant holdout Yerardi as belly-of-the-beast witnesses.

But the heart of the matter remained the mundane business of Bulger and Flemmi shaking down vulnerable bookies from Heller’s Café. Though the bookies had dealt mostly with Bulger’s out-front man, George Kaufman, most had endured at least one moment alone with the marble eyes of Whitey Bulger or the unfriendly smile of Stevie Flemmi. The “other” crimes that supported racketeering charges against the pair reached back into the ancient history of Bulger’s early work in Winter Hill’s sports-betting network in the I970s. Flemmi’s racketeering was linked to gangland murders from the 1960s.

Frank Salemme was the next mob figure to get into trouble. Despite his years on the mean streets, Salemme remained oblivious about the dangers of his boyhood friend Stevie Flemmi. He had no clue that he had spent fifteen years in jail for attempted murder because Stevie tipped off the Boston FBI about where to find him.