Black Mass: The Irish Mob, the Boston FBI, and a Devil's Deal (14 page)

In more ways than one, the underworld picture was in flux. By the time of Morris’s party Howie Winter was out of the way. Bulger and Flemmi were no longer anybody’s sidekicks, and Bulger was making his move upward as a crime boss in his own right. He and Flemmi were moving out of Winter Hill and relocating into new quarters in Boston not far from the Boston Garden, the aged home of the Celtics and Bruins. But by far the biggest change was a whole new approach that he and Flemmi had devised to conduct their underworld affairs. Gennaro Angiulo might enjoy the day-to-day of running an illegal gambling business. Howie Winter too. But Bulger and Flemmi had come up with a new idea that would not only take them out of the daily grind but also provide them with added insulation from law enforcement. They decided to strong-arm gamblers and loan sharks into paying them for the right to do business. They would extort from them a user’s fee. Like a credit card company, they would take a percentage out of every transaction, reinventing themselves as chief operating officers, as collectors of cash payments. It was a brilliant strategy that would soon have Gennaro Angiulo, with an unmistakable trace of admiration, calling the pair the new “millionaires.”

In 1979 Bulger and Flemmi began making the rounds to independent bookies to explain the new deal. Bulger, for instance, cornered one of the smartest sports-betting bookies in the region, Burton L. “Chico” Krantz. The two had a prior history: Bulger had once threatened to kill Krantz over an unpaid $86,000 debt Krantz had incurred to one of Howie Winter’s bookies. Krantz could offer little resistance, and soon he began paying Bulger and Flemmi $750 a month. The bookie, along with increasing numbers of other bookies, kept up those payments until well into the 1990s. By then Krantz’s monthly tribute had risen to $3,000.

These activities had not gotten completely by the FBI’s radar. Trickling in from other informants was word about the moves that Bulger and Flemmi were making on the bookmakers and loan sharks. In June, around the time of Morris’s party, another informant told the FBI that “Whitey Bulger and Steve Flemmi have been in the Chelsea area shaking down local independent bookmakers for payment.” Morris even had an informant who told him Bulger and Flemmi had expanded their collection business to include drug dealers.

But it was as if Morris and Connolly and the Boston FBI didn’t want to hear any of this. Like a drug, their ties to Bulger and Flemmi had evolved into a dependency that was hardening quickly into an addiction. Coming together for dinner at Morris’s Lexington home, they were all having too good a time. It was the end of a decade, and the ambitious agents stood atop a slope with their prized informants, a perch from which they took a long view over their city and saw the promise of FBI careers on the rise.

They saw only what they wanted to see. It was a moment built on a shared premise: the future belonged to them. They’d feed the Mafia to the beast that was FBI headquarters, the press, and even the public’s imagination. It didn’t matter how they did it, or what methods they used, so long as they got there. Glory awaited.

Morris greeted his guests. It was the first of many such gatherings to come. “It was more social than anything,” Morris said. The easy tone of the evening conveyed the feeling that they all belonged to something special, that the playing field of Boston was theirs. Morris was one of many government officials who would recognize eventually that in this instant the rule book was being put aside for good. Something much stranger than the proper, arm’s-length FBI informant relationship was going on in Boston. But at the time Morris went ahead, opened some wine, and filled everyone’s glass. Bulger, it turned out, had indeed brought a gift, a token of affection revealing that the gangster had a sense of humor. He presented FBI agent Nick Gianturco with a little wooden toy truck, a remembrance of the agent’s undercover work in the Operation Lobster hijacking case.

“It wasn’t an adversarial relationship,” Gianturco said afterward. Everyone was happy.

“I do my best to protect you and I may break a few rules, but I break them in your favor.”

Like a curtain rising,
the garage doors at the Lancaster Foreign Car Service flew open in the spring of 1980 on a new era in Boston’s underworld order. Howie Winter had fallen, and a realignment was under way. It was an industry shakeout, and standing in the bays of the repair shop were Whitey Bulger and Stevie Flemmi, arms folded, ready to take center stage and exploit any and all opportunities.

The old haunt, Marshall Motors in Somerville, had been abandoned in favor of this new downtown location. Though some of the former Winter Hill gangsters were on the run, others had come along. George Kaufman, who had operated Marshall Motors as a front for Howie Winter, now operated the Lancaster Street garage for Bulger and Flemmi. In the mornings the bays might be filled with the clanging and banging of mechanics’ tools, but by early afternoon the tone of the place would change markedly. Most days Bulger and Flemmi arrived around one-thirty to take over the show. Whitey pulled into an empty bay and climbed out of his shiny black 1979 Chevy Caprice. The hushed conversations, the stream of visitors—it all revolved around Bulger and Flemmi. And accompanying them was the big and beefy Nick Femia, an enforcer with a reputation as a killer hooked on shotguns and cocaine. Femia, Kaufman, and other wiseguys stood outside as lookouts as Bulger and Flemmi took up in an office inside.

The Lancaster Street site represented an upgrade, the mobster equivalent of a law firm or bank moving its base from the margins to the center of a city’s business district. It was a location that came with certain frills coveted by just about any Bostonian—a couple of blocks west and across the street stood Boston Garden. The Celtics, led by a rookie named Larry Bird, had just fallen short in their surprising run at the Eastern Conference title against Philadelphia.

More important, the Lancaster Street garage was situated in close proximity to the city’s Mafia heartland in the North End. In a matter of minutes you could walk from the garage to the front door of 98 Prince Street, where Gennaro Angiulo and his four brothers oversaw the region’s LCN racketeering enterprise. Finally, there were Bulger’s neighbors a few blocks south. The Lancaster Street garage stood practically in the shadow of the FBI’s Boston field office in Government Center, where John Connolly and John Morris were stationed.

In many ways Bulger was on a roll. Even though their former Winter Hill gang had suffered a crippling blow from the government’s wildly successful prosecution in the race-fixing case, Bulger and Flemmi seemed to have adopted the optimistic view that in life there were no setbacks, only new opportunities. They’d heard that an unaffiliated East Boston wiseguy named Vito was running a loan-sharking and gambling business without the blessing of either Bulger or the Mafia. Soon the gun-toting Femia paid Vito a visit and put a pistol to his head. Then Bulger and Flemmi had their own session with Vito in the back room of a downtown smoke shop and explained the meaning of life. Vito decided to retire, and Bulger, Flemmi, and Femia took control of the East Boston franchise.

No question, when the need arose, Bulger and Flemmi were hands on. If a “client” was late on a loan payment, they would take the wayward one for a ride in the black Chevy. Flemmi would drive with the recalcitrant debtor seated by his side. From the backseat Bulger would whisper in a low but unmistakably firm tone about the need to “get it up” or “face the consequences.” If a second trip was necessary, Bulger and Flemmi would have someone like Femia trash the debtor’s apartment while the two crime bosses talked over the problem during the ride-along.

Usually there was no call for a third ride.

Inside the FBI Connolly and Morris were stuffing the bureau’s files with confidential reports about how down and out Bulger and Flemmi were in the wake of Howie Winter’s fall, but out on the street the two gangsters hardly appeared to be suffering. In addition to coordinating their affairs with the Mafia, the two were busy launching their new tactic of extorting tribute, or rent, from already established rackets. The bookmaker Chico Krantz was now stopping by to drop off his monthly payments, at one point plunking down an extra $5,000—an additional fee Bulger had demanded for settling a dispute Krantz had had with another bookie. Krantz was only one of many bookies now paying such tributes.

There was one hardship, a personal one. On New Year’s Day 1980 Bulger’s mother had died at Massachusetts General Hospital after a long illness. She was seventy-three. Whitey Bulger had stayed on in the family apartment on O’Callaghan Way in the South Boston housing project where he, his brother Billy, and John Connolly had all grown up. It was where Flemmi often picked him up in the late morning in the black Chevy to start their business day.

Bulger did have two other women in his life to comfort him. One was his longtime girlfriend, Theresa Stanley, who lived in South Boston. He’d met Stanley in the late 1960s, when she was twenty-five and aimless, already a single mother of four children. He taught her how to organize her life and to have dinner ready for him each night at the same time. She was always grateful for his presence in her life. He was strict with her children, and he wanted everyone to sit at the dinner table together. But these days, even if he played father to Theresa’s four kids, Bulger often ended his day in the arms of a much younger woman, a dental hygienist named Catherine Greig, who lived in North Quincy.

Despite the loss of their mother at the start of the year, 1980 was a time when both Bulgers were consolidating their power and fast approaching the top of their games. Elected as president of the state senate in 1978, Billy Bulger had established himself as a charming orator and cunning powerbroker. Conservative on social issues—opposing abortion rights and supporting the death penalty—Bulger was an outspoken defender of the working class. He remained impatient with dissent, however, if not intolerant. In words that could have been ascribed to his gangster brother, politicians described having worked with “two Billy Bulgers.”

“If you are going to be just his friend, he’s very polite, very proper, a very nice person, a good host, all that,” George Keverian, the house speaker, said about dealings with his counterpart in the state senate. But, he added, if you opposed Bulger, you faced a different and darker side: “He gets steely-eyed, he gets cold.”

In a number of highly publicized disputes Billy Bulger’s reputation as a vindictive autocrat was cemented. In one, Billy became enraged when a Boston housing court judge refused to fill a clerkship with his handpicked choice. The judge lashed out against Bulger’s raw patronage move by calling Bulger a “corrupt midget.” Payback came through legislation that cut the judge’s pay, reduced the size of his staff, and ended the court’s independent status by having it folded into another branch of the judiciary. Both Bulgers were used to having the last word.

Indeed, the Bulger brothers—each in his own way—seemed determined to make a struggling city theirs. It was a period of economic unrest, of high inflation, with an aging ex-movie actor, Ronald Reagan, on his way to ousting the unpopular incumbent president, Jimmy Carter. It was the dawn of what would soon become known as the high-flying 1980s, the “Me Decade,” featuring yuppies, skinny ties, designer food, and leg warmers, an era of Wall Street greed and corporate takeovers led by mega-financiers like Carl Icahn and Michael Milken.

Strutting into the Lancaster Street garage each day were Bulger and Flemmi to take care of their own mergers and acquisitions. And Jane Fonda wasn’t the only one exercising hard. Both Whitey and Stevie worked out, lifted weights, and stayed fit. Bulger, even at fifty, took his appearance seriously, and he showed up at the garage to flex his underworld power wearing the body-fitting shirts that were in style. There wasn’t a mirror or a windshield he didn’t like. He’d pause, catch his reflection, secure in the feeling that no one—at least not the Boston FBI—was watching what he was really up to.

BUT someone was watching.

Peering out from behind the shabby curtains of a second-story window in a flophouse directly across from the Lancaster Street garage was a group of hard-driving troopers from the Massachusetts State Police. Six days a week, beginning in late April and lasting into July, the troopers were hunkered down at the window in the roach-infested bedroom, chronicling the mob action across the street.

They saw the little things—Bulger and Flemmi preening on the sidewalk between appointments, sucking in their stomachs when a pretty woman walked by or making sure their shirt buttons lined up with their belt buckles. They watched Bulger’s body language downshift into business gear when he was displeased—charging hard at a visitor and jabbing a finger into the man’s chest, swearing at him all the while. When Bulger was done, Flemmi would take over and do the same. More significant, the troopers saw the big things—men arriving with briefcases and betting slips. They watched money change hands. They took notes, and they took pictures. In all, during the eleven weeks they watched, they counted more than sixty noted underworld figures come and go; in fact, virtually every organized crime figure in New England, at one time or another, showed up at the Lancaster Street garage for a meeting with Whitey Bulger and Stevie Flemmi.