Black Mass

by Dick Lehr

  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.

  But as always seemed to happen when events veered dangerously close to Bulger, there was a derailment in federal offices. One of the top prosecutors in the U.S. Attorney’s Office, A. John Pappalardo, decided to use Tim Connolly to get into Bulger’s finances. He turned Tim Connolly over to two handpicked FBI agents who had no ties to John Connolly. They wired the mortgage broker as a way to get an inside look at Bulger’s money laundering. But then Whitey Bulger suddenly stopped dealing with Tim Connolly.

  In the end Tim Connolly was not used in the DEA and Boston police case against Bulger Drug Network because they never knew about the extortion in the back room. And the FBI’s attempt to use Tim Connolly on Bulger’s money laundering never got off the ground. But if investigators and even some prosecutors never knew Tim Connolly’s value when it counted the most, the same cannot be said of Whitey Bulger. He knew all about the threat that Tim Connolly posed, almost immediately after the FBI had him wired.

  Stevie Flemmi said that after Tim Connolly was sent to the FBI, “Mr. Bulger told me that Tim Connolly was wired up and that he was directing [at] us as a target . . . the information came from the FBI.” Flemmi was quite certain the tipoff came from John Connolly.

  Kelly took all of this in. It was a lesson in how hard it would be to bring a case—any case—against Bulger. But it was also a reminder that perhaps, just perhaps, it could be done.

  CHAPTER EIGHTEEN

  Heller’s Café

  On a November day that warned of winter, a state cop took a slow drive by a forbidding brick building with iron bars on the windows and an oversized Schlitz Beer lantern above the front door. Detective Joe Saccardo began nodding to himself as he rolled by slick cars on a skid row. Too many Cadillacs for downtown Chelsea, he thought. Heller’s Café is a bookie joint all right.

  But inside the tavern the proprietor was doing more than logging betting slips. Michael London was shuffling checks, tallying part of the $500,000 in paper he converted into cash each week for the region’s biggest bookmakers. London was just hitting his stride as a back alley banker in 1983. Starting with a small book in a barroom inherited from his father, London had moved up the gambling chain by turning hot checks into cold cash. Bookies now called him “the Check Man.” At the beginning of the 1980s he began shifting away from a local clientele to the big sports-betting network run by Jewish bookmakers with ties to Winter Hill and, to a lesser extent, the Mafia. London had become the man to see when bookies and businessmen wanted to hide profits from the Internal Revenue Service.

  When Saccardo pulled over to a curb, he did some tallying of his own. He had a dozen license plate numbers from the sleek cars that ringed Heller’s Café. Back at the office the state police computer took the numbers and spat out a who’s who of Boston bookmaking: Chico Krantz, Jimmy Katz, Eddie Lewis, Howie Levenson, Fat Vinny Roberto. Even Joey Y—Joseph Yerardi, a wiseguy more than a bookie who put money on the street for Winter Hill and was allowed to collect rents of his own.

  Bingo. Saccardo had found much more than a bookie joint. He had discovered the mob’s bank, a place where gamblers’ losses—in five-figure checks made out to cash or joke names such as Ronald Gambling or Arnold Palmer—were converted into payouts and profits. At its height the bulletproof teller booth in the back of a saloon converted $50 million a year into cash. It also yielded about $1 million in fees to London, who was raking it in on a back street under a tired bridge in a run-down city.

  Fittingly, it was left to Joe Saccardo of the Massachusetts State Police to target Boston’s version of Meyer Lansky. London juggled two accounts in a local bank with about $800,000 in family money and withdrew up to that amount each week as the checks cleared. It was a good deal all around. The local bank got use of the money without having to pay interest, and it winked at London having to report cash transactions of more than $10,000 to the IRS. He worked the system to buy a house in Weston, the wealthiest suburb in Massachusetts, and a summer home in West Hyannisport not far from the Kennedy family’s compound.

  Though most of London’s bookmaking customers were affiliated with Bulger’s gang, he was drawn to the brash braggadocio of Vincent Ferrara, a flashy capo who became such a regular at Heller’s that he had his own table. London saw Ferrara as a comer in the Mafia and hitched his red tavern to Vinny’s rising star.

  London and Ferrara were simpatico, understanding enough about money to see it as more than cash-in-the-pocket and a new car. London began helping to round up freeloader bookies for Ferrara, giving them intimidating pep talks. “You gotta pay one side or the other these days,” he told them. “I’m just letting you know how it works so ya don’t get hurt.” Over time London became the poor man’s version of the Wall Street broker who pushes clients toward an investment banker who gives him kick-backs. The two men had similar tastes. They both bought the same silver two-seater Mercedes, and Ferrara convinced London to take one of the small boutique dogs he bought in New York for $5,000. They also shared loan-shark profits.

  AFTER Joe Saccardo brought the who’s who license plate printout to his bosses, they knew what they had. Instead of settling for a fast gaming raid, they called for reinforcements. A task force of state police investigators and FBI and IRS agents was formed. At times the various agencies did little more than get in each other’s way. It took three years of fits and starts before bugs were spliced into the teller’s cage inside Heller’s Café and taps were placed on two phones. Investigators monitored bugs from a nearby construction trailer for the la
st two months of 1986. When it ended, no one was quite sure of what they had, though they knew this much: Vinny and Mike had a problem. In December the police team rousted the bar, pushing everyone against the wall. But the jammed-up clientele was nothing compared to the boxes of checks carted away to FBI headquarters in Boston.

  Soon afterward London told Jimmy Katz, a bookie whose own day would come, “It’s gonna be a big problem. Not, not immediately. But it will happen.” London knew that the boxes of checks from 1980 to 1986 would tally $200 million.

  Though the confiscated boxes of checks and reels of tape were as rich a vein of evidence as police could have carried away, the whole case bogged down at the FBI in 1987. The bureau was sure there was a Mafia capo in the big stack of stuff but was halfhearted about investigating further. In the U.S. Attorney’s Office, Jeremiah O’Sullivan had just finished the Angiulo case and was ready to take on reckless newcomers. As federal prosecutors reviewed the tapes, O’Sullivan cherry-picked them for his strike force and tossed the rest back. His assessment: we’ll take Vinny, and somebody else really should do London. And, oh, there might be some other stuff in here too.

  INDEED there was. Only doing Ferrara meant taking a pass on the bookies in the line at Mike London’s cashier window who were being extorted by Whitey Bulger and Stevie Flemmi. London once told Chico Krantz, the premier bookmaker with a long-term deal with Bulger, to “shop Italian.” “Stevie can’t hold [Vinny’s] jockstrap. Vinny will work for ya . . . a collection agency, personal protection. Stevie don’t do nothin. This guy here will go to bat for you.” In another Mike London speech, a bookie nicknamed “Beechi” got the sad facts of life: pay Ferrara or “the other guys are gonna get your name . . . Stevie and Whitey.” But nobody in federal law enforcement seemed excited about the evidence implicating Bulger and Flemmi.