I’m reviewing Whitey’s life to determine if his reputation as the most evil of criminals is justified rather than being erroneously posited to us by people who need us to accept it as true. I’ve run through his time up to getting released from prison in 1965 and suggested the next 30 years are the times within which he has made his reputation. Prior to 1965 the worst that could be said of him was he robbed a handful of banks, was caught, and did nine years, some of it hard time, before he got out in ‘65.
As of January 1995 Whitey was a man on the lam for 16 years unconnected with the Boston scene. He traveled over parts of the U.S. finally settling in Santa Monica, California. He lived in a multi-apartment building with his female friend, Catherine Greig, in a third floor walk up with the covered windows that blocked prying eyes from looking in and the inhabitants from seeing out. They lived with little contact with others in a hermit-like existence, hardly one step up from being confined in a cell with conjugal visits.
He was imprisoned by the money hidden in the walls ever fearful of its loss to criminals like himself limiting his ability to make forays from his hole-up. The pillow he put his head on never gave a decent night’s sleep. He depended on an arsenal of guns including military-type weapons that he would never use to maintain what he thought was his freedom. Now he probably sleeps better at night in the Plymouth County jail than he did in Santa Monica where he allegedly stayed up at night peeking out the window at threatening spectres.
I divided these years from 1965 to 1995 into four segments because certain factors exist that make them somewhat easy to segregate out although there may be a small amount of overlapping. The four periods are in sum: The Early Years, 1965 to 1972, 8 years; The Learning Years, 1973 to 1977, 5 years; The Boss Years, 1978 to 1988, 11 years; and The Gathering Years, 1989 to 1994, 6 years. All the murders charged in the indictment occurred in the learning years 11 murders, and the boss years, 8 murders.
The Early Years period is the time he got out of jail up until the time he became involved with the Winter Hill gang. These seem to be years of figuring out what he will eventually do with his life. He’s on parole so he has to watch his step. He’s out of prison at age 36 and has yet to have murdered anyone unlike Martorano, Flemmi, Salemme, Nee, and some of the Mafia people who were veteran murderers by his age. Whitey may have begun his first murders around the time he turned 40 in 1969 when he became involved in the Southie Killeen/Mullen gang wars.
The Learning Years from the time White joined Winter Hill in 1972 up through 1977, a period of about four to five years when he’s an understudy. During this period it was clear that there was one boss of Winter Hill and that was Howie Winter. Howie who took over from Buddy McClean had two close associates, Joe McDonald and Jimmy Simms. Next to associate with them were the Martorano brothers, Murderman John and Jimmy. Whitey was somewhat down the line.
Eleven of the murders alleged in the indictment against Whitey occurred during this time of the learning years when Whitey was somewhat down the command level of the group. Howie, who was in charge, and who was in 2012 charged with extortion has never been charged with any of these murders. The first, Michael Milano, occurred in 1973 and the last Richard Castucci happened in 1976.
According to Pat Nee, Howie had not even heard of Whitey in 1972 when outside interests were trying to establish a Southie gang war truce. Whitey didn’t walk into that group of murderers with much status despite what we are told now. It was probably not until 1974 when Stevie Flemmi returned from his years on the run and Whitey teamed up with him that he slowly accrued power.
Howie ran the operation through 1977. Howie was indicted for extortion by prosecutors in the Middlesex DA’s office under the oversight of our new Secretary of State, John Kerry. He and Sal Sperlinga went to trial for trying to force pin ball machines, of all things, into some bar rooms through threats and intimidation. Howie was convicted and got 18-20 years in prison. That left room at the top.
Although Whitey was not in line for the big job of boss, the race fixing case in 1979 would cause Joe McDonald, Jimmy Sims, and John Murderman Martorano to flee town. Jimmy Martorano who was also indicted in that case was already in prison for extortion.
The whole Winter Hill Gang could have been put out of existence had both Whitey Bulger and Stevie Flemmi been indicted in the race fixing case. Whitey with his record would have been convicted and gone back to prison for what I have called his boss years. However that was not to be.
FBI Supervisor Agent John Morris and FBI Agent John Connolly went to AUSA Jeremiah O’Sullivan and asked him to keep them out of the indictment. They told him these vicious gang leaders were FBI informants. O’Sullivan would later say he didn’t keep them out because they asked but the facts seem irrefutable that he did accommodate Morris and Connolly.
Whitey and Stevie Flemmi’s ascension to the leadership of the Winter Hill Gang can be directly attributed to the FBI and US Attorneys office.