Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (19 page)

That explanation, an exaggeration meant to flatter, didn’t appease Whitey. He looked at Oteri and said, “Yeah, well, I spent nine years in prison and I read a book a day.”

Whitey seems to have resented Oteri. Among the tips Whitey was credited with passing along to John Connolly were repeated and unsubstantiated claims that Oteri’s law office was being used to traffic cocaine. Oteri said that the claims were nonsense. But on more than one occasion, Connolly’s reports cited Whitey as the source of claims that Oteri was not just representing drug traffickers Michael Caruana and Kevin Dailey but that he was in business with them. A report from November 25, 1980, quotes Whitey as claiming that Oteri and other Boston lawyers were snorting cocaine at a fund-raiser for then Norfolk District Attorney William Delahunt at Anthony’s Pier 4 restaurant on the South Boston waterfront. How Whitey Bulger, a convicted felon and, at the time, a notorious hit man, could have known of this is not mentioned in Connolly’s report. A political fund-raiser like that would more likely have been the domain of Bill Bulger or his Beacon Hill peers, not his gangster brother.

Oteri doesn’t believe Whitey Bulger implicated him in drug trafficking or cocaine use. He believes John Connolly did this on his own, as part of a vendetta Connolly held against some defense lawyers. Connolly, he said, had long been rude to him, in court and in public, addressing him, in Southie fashion, as Guinea Oteri. “There was no reason for Jimmy to do this to me,” Oteri said. “I wasn’t that close to him, and he knew I was his brother’s friend.”
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But Whitey’s need to stay engaged and useful as an informant may have been reason enough. He had to regularly come across with tips, whether true or not. And the information went both ways. In 1978, after five men were gunned down during an after-hours drug robbery at a Boston nightclub called Blackfriars, Whitey asked Connolly to give him a copy of the crime scene photos. Connolly got the photos from contacts in the Boston Police Department and handed them to Whitey, who then brought them to a guy who owed one of the Blackfriars victims, Vincent Solomonte, sixty thousand dollars. Whitey said he was there to collect on behalf of Solomonte’s family.

“You remember Vinny, don’t you?” Whitey asked, showing the man a photo of the slaughtered Solomonte. The man paid up. Whitey split the money with Flemmi and John Martorano.
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It was the first, but hardly the last, act of extortion Whitey would commit with the FBI’s tacit or active assistance.

In 1979, John Connolly asked his supervisor, John Morris, to meet Whitey Bulger and Steve Flemmi. That wasn’t so unusual. The next part of the request was. We should do it at your house, Connolly suggested. Out of the city. Morris lived in Lexington, an upscale suburb.
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Morris just nodded and said yeah, yeah. Connolly looked him in the eye. This was serious. Connolly asked Morris to treat Whitey and Flemmi not like criminals but with respect. They weren’t just informants; they were analysts, partners, on the same team.

Bringing gangsters to an agent’s home was against protocol. It was foolhardy, and dangerous, to expose one’s family to criminals who might be able to exploit that knowledge. But Connolly sensed something in Morris even before he asked. Morris had been complaining about the administrative side of his job; he envied the life of a field agent. And he especially envied Connolly, who was a man about town. He knew politicians. He knew everybody. He had respect. Connolly sensed that Morris, in his restlessness and his weakness, could become a useful ally at the bureau.

Morris’s wife, Rebecca, with whom he already had a strained relationship, didn’t like the idea of having criminals in her house. She refused to cook for them and left the dinner to Morris. He made steak, and as they sat around the table Morris kept filling his own wine glass. Whitey regaled him with stories about Alcatraz, and Flemmi talked about life on the run in Montreal.

Both men noticed how many glasses of wine Morris drank.

They were always looking for a weakness.

Whitey and Flemmi were, however, sympathetic to Morris on one point: They appreciated the difficulty of balancing business and a home life. They seemed to spend as much time juggling their multiple and multilayered domestic situations as they did their booming criminal enterprise. Whitey had been with Teresa Stanley for a decade when, in 1976, he moved her and her children from the projects into a two-story, brick-front colonial house he purchased on Silver Street in South Boston, just a couple of doors down from her mother’s home. Whitey moved in, too, sharing the eight-room house, located on a narrow street on Telegraph Hill, around the corner from South Boston High School and the historic Dorchester Heights monument. He was a father to her children, but they never called him Dad. Their nickname for him was Charlie. As much as he loved them, Whitey was quickly overwhelmed by the daily chaos of a house teeming with kids, four of them ages ten to seventeen. There was a part of it that Whitey liked—the nightly family meals, holiday gatherings, and Teresa’s unquestioning devotion. But his business kept him out late at night, and Stanley and her children had to tiptoe around the house in the morning so they wouldn’t wake him. He moved out, telling Stanley he needed more solitude.
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Whitey had actually started seeing another woman a year earlier and was getting more serious about her. Catherine Greig was twenty-four when they met and ten years younger than Stanley. By the late 1970s, Whitey began a new routine. He dined at Stanley’s nearly every night, then slept elsewhere, usually at Greig’s apartment in Quincy.

Theirs was an unlikely pairing. Cathy Greig, who is twenty-two years younger than Whitey, had grown up in City Point, surrounded by the Mullens gang. Her father was a Scottish-born machinist and her mother, a Canadian housewife. It was a dysfunctional household; her father was an alcoholic. Greig, who had a twin sister and a much younger sister and brother, spent most afternoons with her grandmother.
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The family lived in a three-decker on East Fourth Street, a block from the McGonagles, a huge clan that included Paulie McGonagle, the leader of the Mullens, and his brother Bobby, a Boston firefighter.

Many of Greig’s classmates at South Boston High School were happy to go into the military or get a civil service job, something safe and secure with a good pension. Her twin sister, Margaret, aspired to be a secretary. But Greig, voted the prettiest girl in her class, declared in the 1969 Southie High yearbook that her personal ambition was “to have a medical career.”

She was, like Whitey, a devoted animal lover, and flirted with the idea of going to veterinary school. But after high school she enrolled in a two-year program at the Forsyth School for Dental Hygienists, then affiliated with Northeastern University. She proved very good at it; in her second year, Dr. Sigmund Socransky, a prominent periodontist and research scientist, chose Greig to work in his lab. While Greig had previously vowed not to end up a young, married housewife without a career, she nevertheless married Bobby McGonagle, her first serious boyfriend, when she was twenty. When they got back from their honeymoon, McGonagle complained that Greig had sat on the beach and read books the whole time.
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Greig was caught in the riptide of Southie, saying she aspired to a life outside its confines but married into a large, extended family that was Southie through and through.

The marriage was troubled from the start. McGonagle wanted to go out every night; Greig wanted to stay at home. When McGon-agle was caught in a compromising position with Greig’s twin sister, he joked to family members that he had confused the two. Greig was heartbroken by her husband and sister’s betrayal. McGonagle moved out and resumed the relationship with Margaret. Greig was left with the couple’s two miniature Schnauzers. They split up in 1973, but the divorce wasn’t finalized until 1977.

Even before the divorce, Greig had begun dating Whitey Bulger. Either she didn’t know that Whitey had killed two of her brothers-in-law—Donnie McGonagle by mistake, Paulie McGonagle very much on purpose—or she didn’t care. Given her feelings toward the man she married, it may have been the latter, though the circumstances surrounding Donnie McGonagle’s murder had not been revealed in the mid-1970s. Paulie McGonagle, meanwhile, had just disappeared, his body secretly buried by Whitey on the other side of Dorchester Bay.

Charles “Chip” Fleming, one of the Boston police detectives who chased Whitey for years, says Cathy Greig pursued Whitey with purpose, seeking him out at the Triple O’s. “She did it to get back at her husband,” said Fleming. “It was a Southie thing.”
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Even if it was Greig who initiated the romance, Whitey was the one who controlled it.
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He could be charming and charismatic when he wanted to be, and that was the side he showed to Greig. She worked long hours, taking night classes at Northeastern University while teaching in the Forsyth program during the day, ultimately earning her bachelor’s degree. Greig soon started showing off the spoils of dating a gangster. Her co-workers at the dental research facility noticed the new jewels and even a fur coat. “After all she had been through with her ex-husband, I think she just wanted to be loved,” said Linda Hanlon, the former dean at Forsyth and a friend of Greig’s. “And Jimmy was very good to her. Certainly, in a material way he was.”
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Greig’s colleagues wanted to meet her boyfriend and regularly suggested dinners or meetings for drinks, but Greig always demurred, citing some previous engagement. She did, however, constantly sing Whitey’s praises, describing him to colleagues as a generous benefactor of strangers. He paid to fix someone’s teeth. He bought someone else a car. Greig knew that some of her colleagues thought Whitey must be a gangster—he had tons of money, but Greig couldn’t or wouldn’t say much about what he did for a living. She tried to provide an alternative narrative, that he was a Robin Hood figure unfairly maligned by police. Either she was kidding herself or she really believed it. Probably it was a little bit of both.
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Steve Flemmi’s domestic arrangement resembled Whitey’s: He had children with Marion Hussey; the family had dinner together at home most nights; after dinner, he left the house for a younger lover. Marion Hussey was a nineteen-year-old with a baby daughter, Deborah, when she left her husband for Flemmi, then twenty-five and married with two young daughters. Flemmi had separated from his wife and had moved in with Marion and her daughter. Flemmi and Marion Hussey had three children together—Billy, Stephanie, and Stephen—but Flemmi insisted that they take Hussey’s last name. He figured, as Whitey had with his son, Douglas, that kids with his name would have a target on their backs. In 1969, when Flemmi fled to evade murder charges, Hussey worked to support her kids. She waited tables and groomed dogs.

In the summer of 1970, while Flemmi was still hiding from the law, he rented a beachfront house for the family in Montauk, on Long Island. It was his attempt to hold the family together as he figured out his new life. They spent the days on the beach. His nine-year-old son, Billy, got caught in a riptide and was being dragged out to sea when Deborah Hussey, now twelve and a strong swimmer, raced out to save him.
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Deborah had grown up fast: Even before she was in her teens, she had had to look after her siblings while Flemmi was in Canada and Hussey was working. She had also grown into a beauty.

After Flemmi returned to Boston and rejoined the Winter Hill Gang, the family moved into a sprawling mansion in Milton, just south of Boston. Flemmi’s cash bought a swimming pool and tennis courts. The family gathered every Sunday for Italian meals cooked by his mother, Mary. They were often joined by Whitey and Teresa Stanley and other gangsters and their girlfriends. Sometimes, Whitey tucked twenty-dollar bills into the kids’ pockets.

But the wife and kids and the whole domestic tableau did only so much for Flemmi. He always had girlfriends on the side, and they were always much younger. Debra Davis was the one he kept around the longest. She might have stayed around longer had she not found out about Flemmi and Whitey’s relationship with John Connolly and the FBI.

They first met in 1972, when Flemmi, looking for something for one of his girls, dropped into a jewelry store in Brookline. He scanned the display case but was drawn to the young salesgirl standing behind it. Debra Davis was seventeen but seemed older. She was a teenage bride, with her young husband already in jail. And as far as she was concerned, the marriage had ended the moment they’d shut the cell door.

Davis had a bikini model’s figure, deep blue eyes, and a dazzling smile. She feathered her blonde hair in a way that, in the 1970s, reminded people of Farrah Fawcett. She’d grown up in a house with nine brothers and sisters. She got married to escape the chaos at home. But that was over, and now there was this older guy named Stevie flirting with her in the store, and so she flirted back.

Flemmi was always attracted to younger women, and Davis was twenty-one years his junior. He was smitten, and Davis knew he could provide a lot more than her jailbird husband. Soon she was living in a high-rise apartment with Flemmi. He gave her clothes and cars—a Jaguar, then a Mercedes, then a Corvette—and took her to the Caribbean. When Davis wanted a proper divorce, Flemmi paid for it. When her husband complained about it from jail, Flemmi sent word that his cooperation was expected. The young man signed the divorce papers and never bothered her again.
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Davis’s father, Ed, objected to his daughter’s dating a middle-aged gangster and took a sledgehammer to one of the cars Flemmi had given her to underscore his displeasure.
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Ed Davis fell overboard in Boston Harbor and drowned in 1975 while boating with some friends. Flemmi swore he had nothing to do with it, and the death was ruled accidental, but Davis’s family remains unconvinced.

Davis talked about marriage. Flemmi talked about divorce. In a bid to impress Davis, he flew to Haiti to get a quickie divorce from his wife. Flemmi brought Davis’s brother Mickey with him to be a witness, so Mickey could report back to Davis on his noble gesture. But even after going through all that trouble, Flemmi wouldn’t marry Davis and maintained a relationship with Marion Hussey. As the years passed, Davis realized she wanted something more than a free apartment, a free car, and all the money she could spend. She wanted a house, a picket fence, some kids—a normal life. Exactly the things Flemmi couldn’t, or wouldn’t, give her.
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