Black Mass

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 last 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.