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.