James "Whitey" Bulger

For eighteen months, Bulger and eighteen other inmates, all who had volunteered to lessen their sentences, were given LSD and other drugs. Bulger later stated that he and the other inmates had been "recruited by deception," and that they were told that they were helping to find "a cure for schizophrenia". Bulger was transferred from Atlanta to Alcatraz Federal Penitentiary, arriving on November 16, 1959, as inmate 1428-AZ. He became a close friend of fellow inmate Clarence Carnes, alias "The Choctaw Kid" and served alongside men like Mickey Cohen and Alvin Karpis.

According to Michael Esslinger who has authored several books on Alcatraz and conducted extensive interviews with Bulger, he stated Bulger looked back at his Alcatraz years with great nostalgia. He quoted Bulger:

Looking back, Alcatraz was pretty good. You may be surprised to find that I look back at Alcatraz with a sense of nostalgia. My life today would break most men. After 16 years on America's Most Wanted list and living a quiet life on the California coast, I'm back in a cold isolation cell and reflect often back to those years on the Rock. Even though the San Francisco was close, we always felt so far removed from everything. It was like we were on the dark side of the moon. Same faces all of the time, same routine; everyone pretty much felt the same. I wouldn't say that again if I were there under the same conditions today. I'd be in the yard, sitting high up on the bleachers, getting the warm sun, looking out across the Bay, watching the ships and the Golden Gate Bridge. It was the best view from any prison in the world. I'm sure that if men like Capone, Mickey Cohen, Joe Carnes and Jack Twining were alive today, we would reminisce over coffee, having a lot of the same memories of our years there. Going through the old roster, it's like a trip through the cemetery. I had flash backs seeing the names of many good friends. Many I knew for years, how they lived and how they died.

In July of 1962, Bulger was transferred to Leavenworth Federal Penitentiary and in the following year, 1963, to Lewisburg Federal Penitentiary. He was released in 1965, after serving nine years in prison.

Returning to Crime

After his release, Bulger worked as a construction worker before becoming a bookmaker and loan shark with ties to Donald Killeen, the leader of the dominant Irish mob in South Boston. In 1971, Killeen's younger brother allegedly bit off the nose of Michael Dwyer, a member of the rival Mullen Gang. A gangland war soon resulted, leading to a string of killings throughout Boston and the surrounding suburbs. The Killeens quickly found themselves outgunned and outmaneuvered by the younger Mullens. It was during the Killeen-Mullen war that Bulger committed what Weeks describes as his first homicide. According to Kevin Weeks: "Killing Paulie McGonagle, however, took Jimmy longer than he originally expected. Paulie talked a big game, but he wasn't a shooter. Although he never did anything, he kept on stirring everything up with his mouth. So Jimmy decided to kill him. One day while the gang war was still going on, Jimmy was driving down Seventh Street in South Boston when he saw Paulie driving toward him. Jimmy pulled up beside him, window to window, nose to nose, and called his name. As Paulie looked over, Jimmy shot him right between the eyes. Only at that moment, just as he pulled the trigger, Jimmy realized it wasn't Paulie. It was Donald, the most likable of the McGonagle brothers, the only one who wasn't involved in anything. Jimmy drove straight to his mentor Billy O'Sullivan's house on Savin Hill Avenue and told O'Sullivan, who was at the stove cooking, 'I shot the wrong one. I shot Donald.' Billy looked up from the stove and said, 'Don't worry about it. He wasn't healthy anyway. He smoked. He would have gotten lung cancer. How do you want your pork chops?"'

Years later Bulger continued to climb the ranks within Boston's crime syndicate, eventually rising to the highest echelon in organized crime. While Bulger prospered as the most prominent crime mogul of Boston, he led his crime ventures with a code of ethics not to allow his criminal ventures to blur the lines of law abiding people who were not involved in any of the underworld commerce. Weeks remembered:

As a criminal, he made a point of only preying upon criminals, as opposed to legitimate people. And when things couldn't be worked out to his satisfaction with these people, after all the other options had been explored, he wouldn't hesitate to use violence.

Certainly, if he thought there was a chance of this person coming back to cause him some harm, there was no sense in bothering to give him a beating. He might as well kill him...and he did. Tommy King, in 1975, was one example. Although I was nineteen at the time and not yet working for Jimmy, he told me the whole story. Tommy's problems began when he and Jimmy had worked in Triple O's. Tommy, who was a Mullins, made a fist. And Jimmy saw it. The next day, Tommy went to the Old Colony projects were Jimmy was living with his mother and tried to make amends. He said he had been drunk and hadn't meant what he had said the night before. Jimmy told him, 'Don't worry about it. Forget it.' A week later, Tommy was dead. Tommy's second and last mistake had been getting into the car with Jimmy, Stevie, and Johnny Martorano. That night, Jimmy put Tommy in the passenger seat with Stevie and Johnny in the back seat, and told him they were looking for someone to kill. That someone of course was Tommy. As they were driving around, Tommy banged on his supposedly bulletproof flak jacket and joked, 'If we don't find him we can try this out.' The minute he finished the joke, Johnny shot him in the head from the back seat. The bullet went right through his head, splattering blood and brains all over the place, but Jimmy just reached over, propped Tommy up, and put a baseball cap on his bloodied head. A minute later, Johnny said he had to make a phone call and asked Jimmy to pull over by the Dunkin' Donuts in Quincy. He was gone a few minutes, supposedly to make a bet, then got back in the car and the four of them drove off. Jimmy drove around for a few minutes and then found a spot on the Neponset River where they buried Tommy. Later that same night, Jimmy killed Buddy Leonard and left him in Tommy's car on Pilsudski Way in the Old Colony projects to confuse the authorities."

On the Run

According to Kevin Weeks, In 1993, and 1994, before the pinches came down, Jimmy and crime partner Stephen Flemmi were traveling on the French and Italian Riviera. The two of them traveled all over Europe, sometimes separating for a while. Sometimes they took girls, sometimes just the two of them went. They would rent cars and travel all through Europe. It was more preparation than anything, getting ready for another life. They didn't ask me to go, not that I would have wanted to. Jimmy had prepared for the run for years. He had established a whole other person, Thomas Baxter, with a complete ID and credit cards in that name. He had even joined associations in Baxter's name, building an entire portfolio for the guy. He had always said you had to be ready to take off on short notice. And he was. He had also set up safe deposit boxes, containing cash, jewelry, and passports, in locations across North America and Europe including Florida, Oklahoma, Montreal, Dublin, London, Birmingham (UK) and Venice. In December 1994, Bulger was informed by retired FBI Agent John Connolly that sealed indictments had come from the Department of Justice and that the FBI were due to make arrests during the Christmas season. In response, Bulger fled Boston on December 23, 1994, accompanied by his common law wife, Theresa Stanley.

After fleeing Boston, Bulger and Stanley initially spent four days over Christmas in Selden, New York, before spending New Year's Day in a hotel in New Orleans' French Quarter. On January 5, 1995, Bulger prepared to return to Boston, believing that it had been a false alarm. That night, however, Stephen Flemmi was arrested outside a Boston restaurant by the DEA. Boston police Detective Michael Flemmi, Stephen's brother, informed Weeks of the arrest. Weeks immediately passed the information on to Bulger, who altered his plans. Bulger and Stanley then spent the next three weeks traveling between New York, Los Angeles and San Francisco before Stanley decided that she wanted to return to her children. They then traveled to Clearwater, Florida, where Bulger retrieved his "Tom Baxter" identification from a safe deposit box. Bulger then drove to Boston and dropped off Theresa Stanley in a parking lot. He then met with Weeks at Malibu Beach in Dorchester, who had brought with him Bulger's girlfriend, Catherine Greig. Bulger and Greig then went on the run together.

In his memoirs, Weeks describes a clandestine meeting with Bulger and Greig in Chicago, Illinois. Bulger reminisced fondly about his time hiding out with a family in Louisiana. He told Weeks, who had replaced him as head of the Winter Hill Gang, "If anything comes down, put it on me." As they adjourned to a nearby Japanese restaurant, Bulger finally revealed how exhausted he was with life on the run. He told Weeks, "Every day out there is another day I beat them. Every good meal is a meal they can't take away from me." In mid-November 1995, Weeks and Bulger met for the last time, at the lion statues at the front of the New York Public Library, and adjourned for dinner at a nearby restaurant. According to Weeks, at the end of our dinner, he seemed more aware of everything around him. His tone was a little more serious, and there wasn't as much joking as usual. He repeated the phrase he had used before that a rolling stone gathers no moss, which told me that he knew he was going to be on the move again. I got the feeling that he was resigning himself to the fact that he wasn't coming back. Up until then, I always believed he thought there was a chance he had beat the case. However, at that point, there was something different going on with him. I didn't fully understand all the aspects of his case. It would be another six months before it became clearer. Yet at that moment, in that restaurant in New York, I sensed that he had moved to a new place in his mind. It was over.

In the aftermath, Weeks decided to cut a deal with federal prosecutors, and revealed where almost every penny and body was buried. Writing in 2006, Weeks recalled, I had known all along, however, that it would not be easy for anyone to capture Jimmy. If he saw them coming, he would take them with him. He wouldn't hesitate. Even before he went on the run, he had always say, 'Let's all go to hell together.' And he meant it. I also knew that Jimmy wouldn't go to trial. He would rather plead out to a life sentence than put his family through the embarrassment of a trial. If he had a gun on him, he had go out in a blaze of glory rather than spend the rest of his life in jail. But I don't think they'll ever catch him.