Black Mass: The Irish Mob, the Boston FBI, and a Devil's Deal (43 page)

THE first obstacle Wyshak encountered as he set out on the Bulger highway was a mind-set. Many in the U.S. Attorney’s Office wanted to stay religiously focused on the Mafia and follow the FBI’s lead, a long gray line headed for a decade by Jeremiah O’Sullivan and then, in his wake, by assistant U.S. attorneys Diane Kottmyer and Jeffrey Auerhahn. (The pro-FBI contingent was led by Jim Ring and Kottmyer, a competent assistant in the Angiulo case and a dour O’Sullivan disciple addicted to the FBI.) Wyshak’s early effort to target Bulger was never opposed directly. The response was never, “That won’t work.” It was, “Interesting. Let’s talk more.”

Then Howie Winter strayed onto the playing field. By the end of 1989 Howie had been out of jail for a few years and was living in exile in rural Massachusetts, working at a garage and staying out of Boston while he was on parole. Winter had fallen on hard times and was collecting workmen’s compensation from a garage injury. But the lure of the kind of easy money he had made in the 1970s proved irresistible, and soon enough the state police and the DEA got a tip that Howie was moving cocaine. The detectives took the case to Wyshak, the outsider with no history or agenda and no ties to the FBI. Wyshak immediately formulated one of his game plans: an aging and wired Howie talking to Whitey about “Santa Claus.”

But they had to catch Howie first. The snitch network reported that Howie was foolishly taking some orders over the telephone. After sufficient “probable cause” detective work, Wyshak obtained court authority to do a wiretap on Winter’s phone and then held a meeting among federal and state investigators to go over “minimization” rules for investigators listening in on the calls.

The bug was compromised the first day it went up. All investigators had was Howie goofing around on the phone. An informant told them that Howie warned him away from telephone contact. It was a fast education for Wyshak in the ways of Boston law enforcement.

Wyshak had gone about the Winter investigation the way he did in Brooklyn—setting a course of action with several agencies in on the details. In New York it had been possible to collaborate over a cross-section of investigators. But not in Boston. So Wyshak was forced to adopt the prevailing need-to-know strategy. After putting out word that the Howie case was kaput, he began working in earnest on a new plan with a chosen few. Using what a colleague calls “great instincts,” he zeroed in on one of Winter’s cocaine suppliers as someone who would roll. The supplier was a fortysomething ex-convict who had just started a new family and had a wife and baby at home. The investigators built a cocaine trafficking case against him, then gave him the choice: doing heavy prison time or coming on board with prosecutors and staying home with the new family. The dealer was wearing a wire within a year, talking to Howie about distributing kilos of cocaine. In 1992 Howie was arrested as he attempted to sell coke. In a flash, Howie was looking at a minimum of ten more years in prison and as many as thirty if Wyshak could convince a judge that his earlier convictions for race-fixing and extortion made him a career criminal.

Howie was taken to a motel and interrogated by Wyshak, state police detective Thomas Duffy, and DEA agent Daniel Doherty. As if Winter didn’t know, they explained his predicament. He was told: we’re really after Whitey Bulger, who, by the way, hasn’t done you any recent favors. Can we work something out here? Howie listened hard and watched the question hang in the air. He asked to speak to his wife, Ellen Brogna, about it. “Become a rat?” she asked him in horror. “You should tell them to go fuck themselves.” So that’s what Howie did.

In May 1993 Winter pleaded guilty and was sentenced to ten years. Once king of Winter Hill, he left court dressed in a drab gray suit on a drab gray day, a sixty-two-year-old gangster looking at a decade in prison, carrying all his belongings in a brown paper bag. A convicted drug dealer with a strong wife—but no rat.

Wyshak had bagged a big target in Howie even if it didn’t get him to Whitey. And the plea bargain meant much more than one more Winter Hill figure behind bars. It forged a lasting alliance between the high-energy prosecutor and the state police detectives and DEA agents who were aching for another shot at Bulger. For his part, Wyshak just wanted to make cases. So they saddled up.

THE Wyshak posse picked up the trail that had been blazed back in the early 1980s by state police detective Charles Henderson. Henderson had overheard suburban Jewish bookies on wiretaps talking about “Whitey” and “Stevie.” As head of the Special Service Unit, Henderson had arrested all of the bookies at one time or another and now knew they were paying rent to Bulger. Whitey annoyed the combative detective on a personal level. He also realized Bulger was getting a pass on his extortion, that no one else in law enforcement gave a rat’s ass about it except the state police and a few local prosecutors. (In fact the FBI had a formal policy of not stooping to chase lowly bookies.)

But Henderson saw the bookies as a bridge to Bulger and knew that they would be vulnerable to a concerted assault—if one could ever be mounted. Henderson knew well the bitter legacy of the Lancaster Street garage and even something about the Halloran murder aftershocks. But most of all, he was a visceral cop who decided he’d had enough of this bully who swaggered out of South Boston on a pass from the FBI. Henderson did some long-range planning. He needed bookie cases that would enable police to take control of gambling profits by using forfeiture statutes. It was a sure way to get a bookmaker’s full attention. And he needed to hand the bookies over to federal prosecutors like Wyshak as witnesses against Bulger for some kind of racketeering case. As he began plotting his way at the end of the 1980s, he realized that politics was at least as important as evidence.

By 1990 Henderson saw that the timing was finally right. He had just been promoted to head of the uniformed state police. And there was a new lineup at the top of law enforcement that could work together. The new state attorney general, Scott Harshbarger, the new district attorney in Middlesex County, Thomas Reilly, and U.S. attorney Wayne Budd were friends who could work together. One factor plaguing earlier efforts against bookies and organized crime had been the fragmented jurisdictions of county district attorneys. It made it hard to chase bookies with phone taps across county lines. So one of the first moves Henderson made in his new job was to have Harshbarger’s office obtain blanket court authority to chase bookies across county lines. Henderson’s second was to appoint his protégé, Thomas Foley, as head of the Special Service Unit.

The plan was to make cases against bookies that could be handed off to the feds, who could use their tougher sentences to turn bookmakers, accustomed to paying $3,000 fines in state court and never going to jail, into witnesses. The middle-class bookies were more businessmen than archcriminals, and there were not many who would stand up to ten years in a federal prison.

The effort got under way in Middlesex County, chosen because of its heavy betting (it was the state’s most populous county) and because the state police worked well with Reilly, who had been a longtime prosecutor there. Phone taps went up in 1991 and multiplied quickly as one bookie led investigators to another. There soon was an embarrassment of riches, and the state police had to make a fast decision—whether to chase both Bulger’s gang and Mafia bookies. In some fancy footwork, the investigators slyly handed off Mafia bookie “Fat Vinny” Roberto to the FBI but quietly retained control of Chico Krantz and his crew of Jewish bookies paying Bulger.

While Roberto eventually fizzled, state investigators made dramatic progress with Chico, especially when a search warrant uncovered the keys to Chico’s cash box. Krantz played it cozy, but he was intrigued by the idea that he could stay out of jail and get some of his money back if he did a little talking. Whitey was where things bogged down.

Foley was ideally suited for carrying out the next step in the delicate mission. Having worked on special assignment since 1984 with the U.S. Attorney’s Office and the FBI, he knew how to ease the case to federal prosecutors who wouldn’t just turn things over to the FBI for more leg-work. Foley took his pitch and Chico’s predicament down the hall to Fred Wyshak. Foley convinced him that a criminal merger had taken place and power had shifted to Bulger’s gang. Wyshak was so impressed he didn’t make a wisecrack.

BRINGING in skittish bookies looking for a deal to stay out of jail was one thing. Slipping under Bulger’s stranglehold on drug dealing in South Boston was quite another. Throughout the 1980s Southie had been an impregnable fortress. But now a crack began to show.

Timothy Connolly was a mortgage broker trying to outrun his roots as a South Boston tavern owner. He had a simple story of extortion to tell about Bulger putting a knife to his throat for money. But the U.S. Attorney’s Office tried to turn Tim Connolly’s solid single into a home run. They constructed an elaborate plan to infiltrate Bulger’s financial operation, a doomed effort that fell far short of the mark. Just as some in the FBI would have liked, Timothy Connolly was forgotten—almost.

Four years later, in 1994, Brian Kelly bumped into an investigator in a courthouse corridor. “Don’t forget the Tim Connolly stuff,” the investigator said. “It’s good.” Kelly looked at him blankly. Tim Connolly? Tell me about him, Kelly asked.

It had all started, the investigator recalled, in 1989. A car almost cut Tim Connolly off as he walked along a South Boston sidewalk on a simmering summer day. It screeched up the curb, and Connolly squinted into the sun to see inside. With a rush of adrenaline, he saw Whitey Bulger and Stevie Flemmi glaring out at him. The driver barked to meet Bulger at the Rotary Variety Store and sped away.

Tim Connolly was flummoxed. What’s this? he thought with a gnarled stomach. He got an emphatic answer the second he made his way into the dark storage room in the back of the variety store. “You fucker,” Bulger screamed at him, pulling a knife from a sheath strapped to his leg. Bulger began viciously stabbing empty cardboard boxes stacked against the wall.

Tim Connolly’s hanging offense was that he had taken too much time in arranging financing for someone who owed Bulger money from a busted drug deal. Tim Connolly had simply not moved fast enough.

Holding the knife against Connolly’s throat as Flemmi watched the door, Bulger slowly simmered down. As with similar tirades, Bulger’s fury seemed calculated, another episode in the Bulger production called “A Second Chance.” “I’m going to let you buy your life,” he said. It was the classic Bulger scenario and price all over again—$50,000 and how-you-get-it-is-your-problem. Once again a terrified victim was thankful to be paying Whitey for not killing him.

Tim Connolly pleaded for some time and said he had to go to Florida in the next few days. Bulger set the terms: Twenty-five large before he went, and twenty-five on his return. Tim Connolly borrowed $25,000 and brought it in a paper bag to the store. As he left, an appeased Bulger told him, “You are now our friend.”

When Tim Connolly returned from Florida, he took $10,000 more to the store. But Bulger had no time for him now and motioned him to his associate, Kevin Weeks. After taking the money, Weeks looked up and said, “Where’s the rest?” Coming, Connolly said wearily. Coming.

But in fact Tim Connolly was going. Desperate to get away from a killer debt, he began talking with a lawyer who could get him to federal prosecutors. Like Brian Halloran, he was looking for a safe haven. But the bloody history showed that nothing involving Whitey Bulger was simple or easy.

Within a matter of weeks Tim Connolly was swept up again, this time on the other side of the line. The DEA and Boston police were wrapping up their investigation into South Boston and Tim Connolly was subpoenaed to talk about a second mortgage he arranged for one of Bulger’s dealers.

Using phone taps and shoe leather, detectives had worked their way up from a street dealer to the highest level in Bulger’s cocaine network. The evidence included taps on the phone of a dealer who had lost money in a deal involving Bulger—the same dealer who got Tim Connolly summoned to the variety store. The detectives knew nothing of the threat to Tim Connolly but wanted to find out if he was financing drug deals through his banking connections. What the local police also didn’t know was that Tim Connolly was already dealing with the FBI after making his way to the U.S. Attorney’s Office.