Black Mass

“We have to help ’em,” Ferrara urged. “Their families, lawyers. Some of us are in trouble.” Ferrara wanted Sagansky and an associate who’d accompanied him, another aging bookie named Moe Weinstein, to start paying “rent.” During the regime of Gennaro Angiulo, Sagansky had operated without having to do so. But Ferrara said those days were over, and he wanted a show of good faith in the form of $500,000. He told Sagansky that such a sum was nothing to a millionaire like him, and that Sagansky had “class.” “Help us,” Ferrara said.

Sagansky would not. Even though he was seated in the windowless storeroom surrounded by Ferrara and his muscle, Sagansky tried persuading Ferrara that his gambling business was kaput, that it had “plummeted to nothing.”

Both sides cried poor for a while until Doc had enough. “I’m not gonna give you no bankroll,” he said.

Ferrara exploded. Mob enforcer Dennis Lepore leaned down to get into the eighty-nine-year-old’s face: “You don’t have no alternative. We want something now. And you’re lucky it ain’t more. This is a serious request. You understand?” The venom poured from Lepore’s lips: “What are we playin’, a fuckin’ game here, pal? You reaped the harvest all those fuckin’ years! This is something you’re going to pay now. We want it. We’re not asking.”

To induce cooperation, an angry Ferrara then threatened Sagansky that his pal Weinstein would be held hostage until he came up with the $500,000. Doc and Moe were given some time alone in the storeroom. “I’ll never see you again,” Doc said. “Now what should I do?” Weinstein stated the obvious: “Guess you’re going to have to give it to ’em.” The two old men promised to get the money, and Ferrara released them.

The next day, as investigators watched undetected from a safe distance, Weinstein carried a white plastic shopping bag into a restaurant at the Park Plaza Hotel. He handed the bag to Ferrara and Lepore. Inside was $250,000 in cash, the first installment. The two mobsters hurried back to the Vanessa’s storeroom and gloated as they split up the money into six shares of $40,000. “Those assholes, this better be real money,” a flush, cash-happy Ferrara joked to Lepore.

Even without all of the dialogue, the Globe story hit a nerve. FBI officials and federal prosecutors, particularly Jeremiah T. O’Sullivan of the Organized Crime Strike Force, were incensed. Their investigation of Ferrara was still ongoing, and they wanted to know how word about Vanessa’s had gotten out. But the reporters had no obligation or reason to explain to the authorities where their story had started. They were not about to complain about Connolly’s propensity for chatter.

IN FACT it turned out that Connolly wanted to talk a lot about Vanessa’s, or, as it was confidentially referred to, “Operation Jungle Mist.” The agent developed a kind of stump speech in which he described Vanessa’s as the second in a “trilogy” of major Mafia bugs (the first being the 98 Prince Street bug) that the FBI would never have gotten if not for his work with Bulger and Flemmi. “They were without a doubt the two single most important sources we ever had,” Connolly liked to say in a flourish at the end of this proclamation.

But as they so often did, Connolly’s claims upon closer scrutiny proved to be overstated. Bulger and Flemmi were the unnamed informants Connolly referred to during his sidewalk moment with Lehr of the Globe in early 1988. In this regard, it was a shining moment of genuine, singular intelligence. The evidence from the tapes later helped convict Ferrara, Lepore, Russo, and Carrozza of extortion and racketeering. But most of the credit for steering the FBI toward Vanessa’s actually belonged to Flemmi rather than to Whitey Bulger.

Even though Vanessa’s was listed in city records as being owned by a couple from the affluent suburb of Belmont, the eatery was in fact controlled by Sonny Mercurio, a Mafia soldier and pardoned murderer. (Later Mercurio himself would become an FBI informant.)

In April 1986 Flemmi began telling Connolly about Vinnie Ferrara, and how Ferrara was working with Mercurio, J. R. Russo, and Bobby Carrozza out of the Italian eatery. Flemmi, not Bulger, was attending the meetings, where the pending business was sorting out the underworld action between the Ferrara faction and Bulger’s gang. Following one meeting in early August, Flemmi explained that Mercurio was “friendly” with him and Whitey Bulger, “from the days when he was a messenger and liaison between ‘The Hill’ and Jerry Angiulo.” Flemmi added that Mercurio was in charge of setting up the session between the groups to discuss changing the payoff on the illegal daily numbers games so that they could all rake in even more profits.

Flemmi attended another meeting a week later; afterward he once again provided Connolly with a full account—about the ongoing negotiations to change the payoff odds on the illegal numbers games and about plans to distribute illegal football betting cards during that fall’s football season. He told Connolly, “The Mafia intends to chop up the whole city and state, if possible, by controlling all independent bookmakers.” He reported that the “Mafia was on the march” into the suburbs and said that he’d made his way to the secret session “by taking an elevator up from level 5 to the service area.”

The meetings continued, and Flemmi began providing more details about the storeroom’s location, layout, and security. “The storeroom is located two doors from Vanessa’s,” he told Connolly on August 18, 1986, “which is used for the meet, is wired with an alarm system, but the system does not seem to be operative. In addition to the alarm system, the area is patrolled by a security service.” During one of their late-night huddles at Connolly’s home at the end of August, attended by Bulger and Jim Ring, Flemmi even drew up a rough sketch of the Vanessa’s floor plan.

This kind of information provided ample probable cause for the FBI to win court permission to plant a bug inside the eatery’s storeroom—and then some. The diagram, for instance, was somewhat over the top, Ring said later. “I think it’s pretty stupid,” the supervisor said about Flemmi’s artwork. “I don’t need a diagram to figure out how they got in there,” he said. Better to have agents conduct surveillance than give away the FBI’s plans to a criminal informant. “You get too far down a discussion like that with an informant, the informant is learning too much from your questions,” said Ring. “Despite Mr. Flemmi’s great skills,” he added sarcastically, “the people we have are far better, and I relied upon our technicians to put the bugs in the right place so that they functioned.”