Whitey: The Life of America's Most Notorious Mob Boss - Softcover

DICK LEHR is a professor of journalism at Boston University and a former reporter at the Boston Globe, where he won numerous awards and was a Pulitzer Prize finalist for investigative reporting. He is the author of The Fence: A Police Cover-up Along Boston's Racial Divide, which was an Edgar Award finalist and a Boston Globe bestseller. He is the co-author of several other books, including the national bestseller and Edgar Award-winning Black Mass: Whitey Bulger, the FBI, and a Devil's Deal. 

GERARD O'NEILL has won the Pulitzer Prize in journalism as well as many other national journalism awards. He was the longtime editor of the Boston Globe's award-winning investigative team. He co-authored Black Mass and also, with Lehr, The Underboss, as well as Rogues and Redeemers (Crown 2012), a political history of the Boston Irish focusing on the city's most famous mayors.

1

September 17, 1981

At ­mid-­afternoon on a dying late summer day, the stunningly beau­tiful Debra Davis climbed into the snazzy, ­two-­seat Mercedes con­vertible that her boyfriend had bought for her and drove away from the home they shared in the suburb of Randolph, Massachusetts. She headed north, her destination South ­Boston—­East Third Street, to be exact, to a house located on the eastern side of the compact neighborhood shaped like a finger sticking out into Boston Harbor.

Her boyfriend, Stevie Flemmi, wanted to show her ­something—­at least ­that’s what he’d said on the telephone. He wanted to give her a tour of the ­Cape-­style house he’d bought for his parents. The closing was earlier that very same day, and Stevie had paid the full purchase price of eighty thousand dollars, an act of generosity so that his parents would not be saddled with a mortgage.

Debbie exited the interstate. She began snaking her way through the streets of a community known as mostly ­Irish-­American, insular and famous for its “Southie Pride.” While she was familiar with the neighborhood, able to navigate the grid of narrow streets, many of which were ­one-­way and dizzying to outsiders, if Stevie had been at the wheel he would have been able to make his way blindfolded. Stevie Flemmi had grown up in another part of Boston but Southie was now a key venue for his business ­interests—­ever since 1974, when he signed on with a gathering force in the ­city’s underworld: the legendary boss of Southie’s Irish mob.

Debbie and Stevie had been together for that long, too. She was a teenager in late 1974 working behind the counter at a jewelry store on Beacon Street in Brookline when he’d spotted her. Stevie was significantly older: Debbie was nineteen; he was forty. Stevie had liked what he ­saw—­the flowing blond hair, the blue eyes, the glamour of a ravishing young ­thing—­and decided she was for him. He paid for her divorce from a brief mistake of a marriage, and the two were off and running. But at her age seven years was a long time to be in a relationship. Debbie had met someone else and wanted out. Stevie ­didn’t think so; he wanted in, now and forevermore. An unmistakable tension had surfaced between the two.

Making her way down East Third Street, Debbie pulled up to the curb outside the house numbered 832. She could see that the ­one-­ and-­a-­half-­story Cape Stevie had bought was positioned oddly. The front of the house did not face the street the way most houses do; it sat sideways. And it stood opposite another house that was its mirror ­image—­two houses facing each other with only a small, shared yard separating them. Someone standing at the kitchen sink of one house could practically reach out to hand a cup of sugar to the neighbor standing at the window of the other.

The houses were in fact built as a pair in 1965. A year later a ­thirty-­two-­year-­old state representative named Bill Bulger bought one. Ever since, Bill, his wife, and their growing family had lived at 828 East Third Street. When the twin house came on to the market in 1981, Stevie made his move. He’d talked to Debbie about wanting his parents to be nearer to him and to be safe. They’d recently been mugged in Boston. The house for sale at 832 East Third Street, situated in his South Boston stomping grounds and next to the home of Bill Bulger, a rising power in Massachusetts politics, certainly satisfied Stevie’s idea of a safe haven.

Debbie Davis waited in her Mercedes. The day that began in bright sunshine was now mostly cloudy, with cooling temperatures and a quiet breeze. Soon enough Debbie saw Stevie’s car coming down the street. She saw that Stevie was not alone. Stevie had arrived with the older brother of neighbor Bill Bulger.

James J. “Whitey” Bulger. The ­city’s most menacing and beguiling gangster, a crime boss who embraced the role as ­slayer-­in-­chief, in large measure because he understood that ­hands-­on viciousness created the footing for him to rival leaders of the larger, more organized La Cosa Nostra. That Whitey Bulger also seemed to find pleasure in the terror only added to his monstrous aura.

Debbie Davis should have run for it, but she did not.

When Debbie and Stevie Flemmi first began dating in 1974, Debbie’s father complained angrily to her mother, Olga. In particular Edward Davis did not like their difference in age. But Olga basically ignored her husband’s concerns; they’d separated that year and relations were not friendly. “He had a terrible temper,” Olga said. The next year, 1975, Edward drowned in a boating accident.

For her part, Olga thought Debbie was “of age” and old enough to make up her own mind. “She said she’d met a nice guy who wanted to take her out to eat,” Olga said about Debbie’s first mention of Stevie. Besides, once Debbie began bringing Stevie around, Olga liked him. “He was always very polite.” Olga knew one other thing about Stevie, that he was “a bookmaker,” but that was all she wanted to know, and Debbie never talked to her about her boyfriend’s business interests.

Instead, Olga appreciated that her daughter seemed happy. Stevie paid for everything, including one apartment after another the couple shared. He lavished Debbie with money, and she built up a wardrobe of expensive clothes, shoes, and pocketbooks. He’d bought her a Jaguar, a Corvette, and now the Mercedes. They socialized with Stevie’s associates, be it at fancy restaurants downtown or Triple O’s, the bar in Southie, with its nickname the “Bucket of Blood,” that served all of his ­gang’s needs, whether for business or pleasure. They traveled to faraway places, and earlier in 1981 Stevie had even paid for a ­one-­week vacation to Acapulco for just Olga and Debbie. It ­wasn’t as if Debbie was looking to meet someone, but, ironically, during this mother-­daughter getaway, paid for by Stevie, a new man did enter Debbie’s life.

“He met us,” Olga said. “He approached us while we were at dinner.” Debbie was enchanted by the suave, millionaire son of a Mexican oil baron, and the two spent enough time together that a smitten Debbie did not want to go home when the week ended. She did go home, but soon after returned to Acapulco to be with him again. “He was a very nice gentleman,” Eileen, Debbie’s older sister, said. “Treated her like a lady, a princess.”

By summertime Debbie was telling her mother that this was the guy, and she was going to break up with Stevie. By then Stevie had discovered something was up. He’d gone through her things, found her address book, and discovered a new entry for the man from Acapulco—­name, telephone number, address. “I told her she was crazy,” Olga said. “Why did she leave it around? I would have kept it for her.”

Olga had a ­front-­row seat to the widening chasm. Debbie, on the one hand, was talking more and more about leaving Stevie Flemmi for the new love interest, while Stevie was suddenly and excitedly talking about marriage. In August, Stevie had stood up right there in ­Olga’s living room, put his arm tightly around Debbie, and, in full denial, announced, “We’re going to get married in September.”

It was as if by squeezing Debbie Davis and issuing his marital declaration, Stevie was reasserting his claim on the young woman who’d long been such a delight to him. She belongs to me, he was ­saying—­even if his woman was thinking otherwise, to the point that come the afternoon of Friday, September 17, 1981, when she agreed to meet Stevie in Southie, she had a secret plan to fly on Monday to Acapulco.

Stevie Flemmi was no longer trusting of Debbie Davis. But he was not alone. Whitey Bulger did not trust her, either. In the beginning Whitey might have made fun of Stevie for bringing his new young thing around to Triple O’s, saying she was underage and could not be served, but very quickly he came to detest her. “She had a lot to say and was very loud about it,” Lindsey Cyr, one of Whitey’s girlfriends, recalled.

Lindsey was at Triple O’s one night waiting for Whitey, and over the drone of the crowd she could hear Debbie Davis’s voice at the other end of the bar. Debbie was bragging to a group of hovering men that her boyfriend controlled the ­city’s underworld. When Whitey arrived, Lindsey chided him. “This lady down the bar is going out with the head of the underworld. Here I thought that was you.”

Whitey took it in. He saw a woman who was noisy and reckless, a woman who, from his perspective, was a risk. And increasingly she got in the way, between him and Stevie. “Bulger kind of resented the fact that I ­didn’t spend enough time with him in our business,” Stevie said, “and that I was kind of like not being available as often as I should be.” The two associates had a policy of not talking on the ­telephone—­a Whitey rule to avoid possible electronic surveillance. The way it was supposed to work was that Whitey would signal Stevie on a beeper; Stevie would leave his house to find a “clean phone” and then call Whitey back. But too often Whitey dialed Stevie’s beeper, waited for the call back, but the call never came. Stevie was with Debbie and ­didn’t want to be bothered, which left Whitey staring at his beeper.

“He was very upset about it,” Stevie said.

In March, for Debbie’s birthday, Stevie had taken her out to an expensive restaurant in Boston, and right smack in the middle of dinner his beeper went off. Whitey was trying to reach him. “I called him back and he said that he wanted to meet.” Stevie balked, explaining the situation. “I’m having a birthday party.”

Whitey was apoplectic. He told Stevie to send Debbie home. Tell her he’d take her out another night. “You got to be here,” he ordered Stevie. So on that night, Stevie did what he was told and reported for duty.

By ­mid-­1981 the matter of Debbie Davis had become untenable. Stevie had admitted to Whitey he’d shared certain information with her—­extremely sensitive information that was closely held and vital to their business survival. Stevie tried to explain to Whitey why he did ­it—­that his frequent leaving her, and his refusal to say why, had strained the relationship. “She probably figured it was another woman, you know,” Stevie said. The tension between them built to where, in frustration and worry, Stevie told her, “Listen, we have to meet someone.”

That ­someone—­a person whom Whitey and Stevie often met to talk strategy and all manner of underworld ­affairs—­was an FBI agent named John Connolly. “We have a connection,” Stevie told Debbie. “John Connolly, FBI agent.”

This was bad. This was a connection that went to the heart of Whitey’s world, one that in 1981 was operating at full throttle, was responsible for much of Whitey’s success, and was fruitful for the trio involved, meaning the two crime bosses and their FBI agent. While only Whitey and Stevie knew the full contours of the special relationship, the mere disclosure of a “connection” was radioactive. In Cold War politics, it would be like leaking secrets about ­nuclear-­bomb making.

Instantly, Whitey knew what had to be done. If Whitey needed justification for Stevie beyond the shocking breach of security, he could play off of Stevie’s jealousy. Whitey, as always, was up-to-date; he knew about Debbie’s new gentleman caller in Acapulco. This was a ­no-­brainer. This was business.

The front door of the ­Cape-­style house was unlocked. Whitey and Stevie stepped inside first. Debbie was behind them. She saw a kitchen off to the left. Directly ahead a set of stairs led to the second floor. To the right of the stairs, a hallway ran ­toward the rear of the house, past a living room and a bedroom. Stevie headed down the hall, where Whitey, already ahead of them both, was in the bedroom.

Debbie Davis followed Stevie. She had little time to look around, and when she approached the back bedroom Whitey stepped out into the hall. His attack was lightning fast. Whitey seized her by the throat with his hands and began to shake her like a rag doll.

Debbie, gasping for breath, was ­dying—­although blocking her airway was not the actual cause of death. Her death from manual strangulation resulted from what is known in the field of forensic pathology as the occlusion, or obstruction, of blood vessels supplying blood to the brain. The pressure of a strangler’s hands against the neck is so powerful and profound that it crushes the ­neck’s internal structures. And because the strangler has to alter his grip as the victim struggles, the degree of pressure varies—­resulting in a roller-­coaster ride of terror in those final moments as waves of blood course in and out of the victim’s head.

Exactly how Whitey strangled Debbie ­Davis—­and how long it took—­will forever be in dispute, a discordance resulting from two differing accounts. Whitey later told a confederate that the young woman was still alive when he hauled her downstairs into the cellar and de­posited her into a chair. In this version, Whitey likely questioned Debbie as to whether she’d told anyone about the “connection” at the FBI. Following that, her mouth was sealed with duct tape and Stevie leaned over her, kissed her forehead, and said, “You’re going to a better place.”

Stevie Flemmi repudiated that account. He insisted that Whitey finished killing her upstairs in the hallway, where Whitey “grabbed her by the throat and strangled her.” Stevie denied kissing her on the head or uttering the line about her going to a better place. “This happened very quickly,” he testified in court years later about a ­cold-­blooded murder he said was “traumatic” given his relationship with Debbie.

Despite the conflicting accounts, what is not in dispute is that Whitey Bulger strangled a woman who had come to know too much and posed a risk to him as long as she lived. So she died. Then, confronted with a corpse in the house that would soon be Stevie’s mother’s, a house where Whitey, Stevie, and FBI agents would eventually hold secret ­meetings—­meetings that at least once included a ­drop-­in from neighbor Bill ­Bulger—­Whitey was still not done with the ghastliness. He handed Stevie a pair of pliers and instructed him to yank the teeth from the lifeless Debbie Davis to hamper authorities from ever being able to identify her through dental records. Making Stevie pull the teeth from the woman he said he loved was yet another way for Whitey to impose his primacy and authority.