In 1990, Whitey Bulger had been at large in and around Boston for twenty-five years. Virtually alone among serious criminals, he had never served a day in jail during that whole period. He’d been subject to a State Police investigation back in 1983, but that was abandoned after several attempts to perform electronic surveillance on him were compromised, often within hours after the bugs were put in place. To some people, this just enlarged the legend of Whitey Bulger, as if he had almost supernatural powers to detect threats to him and his operation. To others, though, it was simply proof that he was very well connected, and that he had cultivated a law enforcement mole, or possibly several moles, who were in a position to know what was coming, and were inclined to tell him.
Bulger’s activities were all pretty much standard mob stuff, just more of it. Tons more. And unlike most mobsters, Whitey operated pretty much alone. He worked only with Flemmi and sometimes a young hood named Kevin Weeks. And it was always Whitey who made the decisions. Also, he kept his own counsel. Nobody ever told him what to do about anything. Other mobsters had their women, their bling, and their corner tables at name restaurants. Whitey was known to hang out in Southie, but he was rarely seen, and few people in law enforcement even knew what he looked like. When I got on his case, there were only about half a dozen photographs of him that were at all current, usually grainy telephoto shots of him in a Red Sox cap, with dark aviator glasses covering his eyes, taken from hundreds of feet away. I could tell the basics: five-ten, thinning hair, upturned nose, killer eyes. But I couldn’t be sure I’d recognize him on the sidewalk, or in a car.
He’d read those books on military strategy in prison, and informants told us he had devoured a lot more true-crime books since then. And it showed. He never lost his focus, always planned ahead, and kept it simple. He left no incriminating papers around; kept everything in his head; talked only on pay phones, and then said little; even in person, he kept the conversation very brief, and let his ice-cold eyes say the rest; and he lived out of a suitcase, ready to jump the moment things got hot. No records, no bank accounts, no place of residence. When he was younger, he’d had a bunch of girlfriends—and, according to one informant, a taste for watching nude girls have sex behind a two-way mirror. But now he’d narrowed his women to just two—the former dental hygienist Cathy Greig, and Theresa Stanley, a mother of four who’d worked at the Massachusetts Convention Center that was home to many appointments of Billy Bulger. Both of them were much younger than Whitey, who knew the game. Eventually, of course, he took off with Greig, after dumping Stanley. Greig always knew about Stanley; Stanley had not known about Greig.
Whitey was in his early sixties by the time we went after him, but the photos showed that he could still rip you apart. Every day, he hit the weights, and he had developed the sort of build—thick shoulders, powerful arms, heavy chest—that seemed designed for strangling people with his bare hands. Despite the muscles, it was the eyes everybody remembered. Ice-blue, under clenched eyebrows, they could stop your heart; no one who saw them ever forgot them. Them and a tight, angry mouth that was always ready with obscenities. If the edges of his mouth ever turned up, it wasn’t a smile.
The press may have called him a vicious mobster, and we certainly thought of him that way. But because he’d never been arrested, people could think of him however they wanted, and a lot of people around town made him out to be a comic-book villain, or even a folk hero. There were stories about how he helped old ladies cross the street and punished bullies. Maybe if his criminal activities had been confined to gaming and a few drugs on the side, sure. But they weren’t. The guy was a murderer, and it was the murders that set him apart. It wasn’t his way of thrusting a gun in the victim’s face to fill the head with lead. Nor was it the arsenal of guns he had—even though the count approached a hundred, with dozens of submachine guns and automatic rifles in the mix, enough to arm a small battalion.
He used them plenty, and often close-up. But he loved to kill with his bare hands. To strangle people, bringing his fingers around the neck, his thumbs feeling for the windpipe, while his eyes bulged and reddened, his face turned savage, and his chest heaved from the effort. It’s not easy to snap someone’s windpipe with your bare hands, especially if your victim is fighting for their life. Guns are much easier, but less intimate. With one young woman he strangled, he lurched at her, knocked her back onto the floor, hooking his legs under her, and sprawled forward onto her, chest to chest, as he reached for her neck.
In those days before DNA analysis, dental records and fingerprints were about the only ways to positively identify a body. So, to disguise the victim’s identity, when he’d finished the kill, he’d jerk the victim’s mouth open wide, then insert a pair of pliers to yank the teeth out one by one while the blood welled up. He’d drop the teeth into a bag to dispose of separately. The blood must have been everywhere. The body would be hauled off somewhere to a shallow grave where it would be wished away.
Some of this we knew then, and the rest we learned later. But we knew enough then to realize that, formidable as Whitey Bulger was as a mobster, “mobster” didn’t begin to describe him. Habitual murderer was closer, but psychopath was it.
This made our intentions simple. Stop him.
Like everybody else, I’d known enough about Whitey to give me a vague impression but few details. It wasn’t until I joined the Intelligence Unit back in 1984 that I got a fuller idea. The IU had put together detailed files on hundreds if not thousands of gangsters of potential interest, many of them with names like Bobby the Greaser, Shawn T. “Rooster” Austin, and “Sonny Boy” Rizzo. The files were all stored in a thick block of filing cabinets in the State Police’s main office in Framingham. The clips and reports went back all the way to the 1930s, many of them curled and yellowing, with pencil notations and smudged typewriting. Not too many people went down into the basement, but I did. From my first days with Mattioli back in 1984, every few nights I would bring home a dozen or two of the files to pore over.
Whitey’s wasn’t the thickest. That honor went to Angiulo, since as a Mafia chief he’d been so public, and he was at it for such a long time. But the material on Whitey was plentiful—police reports, informant interviews, military records, newspaper clippings, court records from the early days. I spent plenty of time on other mobsters in the LCN and Winter Hill, trying to see the connections, the bloodlines. But I kept coming back to Whitey. He was different. Unlike so many of the others, he started up on his own. He had no brothers in the business; didn’t learn from his father; and created his own organization. He had Flemmi, yes, but he himself was always a mob of one. A survivor, that’s what he was. Doing whatever it took. It was like with the bank robbers he organized, or his being the bodyguard for Donny Killeen, only to split when things got hot. Whitey was always about Whitey.
The people in the LCN were more colorful, but they were organization men. The Winter Hill people were just killers, but with an eye out for a buck. But Whitey’s mob was a much looser outfit that he shaped and reshaped as necessary. In that sense, it was brilliant. Small enough to be reliable and absolutely trustworthy, answerable only to him, flexible enough that it could take on almost any job, and terrifying enough that those who encountered it did what they were told.
What was he after? I thought about that a lot. You have to if you’re going to have a chance at catching someone like him. You have to know where he’s likely to go, so you can be there first. Like most mobsters, he wanted power and control, and the money that those things can bring. That was a given. In this, he was basically like his brother in the statehouse, although his brother maintained a certain respectability. That’s understandable, after his impoverished childhood. Who wouldn’t want security? But he had that other thing, the blood lust, that loomed over everything else, the desire to be the one who decides if others live or die, and the thrill of being the one to make it happen, either way. For him, control was total.
He was disciplined, like with the regular weight lifting. He’d get in on other people’s drug deals, but not allow anyone in his circle to touch them. He never smoked, rarely drank, and watched his weight. Other wiseguys had their fast women, big cars, lavish houses, and jewelry, but not Whitey. He had those girlfriends, and kept two, to make sure that neither took over.
Start to finish, throughout the investigation Whitey gave us almost nothing. He was like air. You know he’s there, but you can never see him. One of our informants said that Whitey spent 98 percent of his time on business and 2 percent on pleasure, which is the reverse of most criminals. Like those World War II generals, he didn’t act without thinking about the consequences. Would the victim rat him out? Where would he hide the body? Who might talk? How can any talkers be silenced? What then?
He never spoke about business in an enclosed space. In his car, the interior panels and floor mats were touch-sensitive, so they’d give off a warning signal if anyone tried to plant a bug. We learned that the hard way. He once juiced up a Chevy Malibu to be his getaway car. It could do 160, and then release a billowing fog of oily smoke and an oil slick to blind any pursuers and send them spinning off the road. That was the mentality.
I spent weeks poring over his file. There were bits here, bits there, but nothing that really added up. I’d try to put the files into order, at least in my head so I could get a read on the guy, and how he got that way. I pored over the few mug shots from long ago, and some surveillance photos taken since then, the early ones showing a cool-guy smugness, the later ones burning with anger. In the end, I realized the files would only take me so far.