LITMIR.BIZ

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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, Teresa 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 Teresa’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 hand-picked 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 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.

      Like a silent movie—no words and all action—the garage provided a panoramic shot of the whole of the Boston underworld. And the action filling the wide screen in living color contrasted sharply with the narrow snapshot of Bulger and Flemmi that the Boston FBI was planting in the bureau’s files and in the minds of anyone who asked about the two gangsters.

      The state police surveillance had begun quite by accident. Trooper Rick Fraelick happened upon the garage one day while he was driving in the neighborhood on a tip about a stolen car ring. He drove down Lancaster Street and noticed George Kaufman and some of the other mobsters standing on the sidewalk. He pulled over and, out of their view, checked out what was going on.

      It was a jaw-dropping moment. He recognized other mobsters coming and going. He saw Bulger and Flemmi. Fraelick returned to headquarters and told Sergeant Bob Long, the supervisor of the Major Crime Unit. Long accompanied Fraelick on a few drive-bys to view the activity for himself. They felt the adrenaline rush that comes with the prospect of a potentially big case. The question was where to set up. Directly across from the garage was a run-down brick building, 119 Merrimac Street. The first floor was a gay bar. Upstairs rooms could be rented. It was a dump, a cheap place where winos crashed. There was little privacy: the uninsulated walls were made of thin wood paneling that a fist could pass through easily. Posing as a gay man, Fraelick rented the room looking directly on to the Lancaster Street garage, and starting in late April, he and Long and trooper Jack O’Malley began documenting Bulger’s affairs.

      Other troopers were involved along the way, but these three were the principal investigators who arrived early each day and took up at the window, usually in shifts of two. The men were all local. Long, in his midthirties, had grown up just outside Boston, in nearby Newton, the fourth in a family of ten kids. His father was a lawyer, and since he was a boy he’d dreamed of becoming a state trooper. Long was a jock in high school, even won a partial basketball scholarship to a local junior college, but once he blew out his knee, his sporting life was over. Less than nine months after earning a college degree in criminal justice from City College in San Francisco in 1967, he was back in Massachusetts standing at attention at the state police academy.

      Now in charge of a special investigations squad, Long had handpicked Fraelick and O’Malley—both, like himself, athletic and solidly built, the brown-haired Fraelick originally from the North Shore and the reddish-blond O’Malley from Boston’s Dorchester neighborhood and a family of cops. (O’Malley’s dad, a Boston cop,

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