Re-Examining Whitey Bulger: The Four Seasons: Early Years, Learning Years, Boss Years, Gathering Years: Part Five

Dorchester Heights
South Boston

The Thirty Years of Whitey Bulger’s life I’ve broken into four parts. I’m doing this for the purpose of trying to determine for myself if Whitey is the worst of the worst criminals or has been given that identity by people who have ulterior motives in elevating him to a status far beyond what he deserves. The Early Years (1965-1972) and The Learning Years (1973-1977) that I spoke about yesterday ended when Howie Winter went off to prison. Then followed the Boss Years (1978-1988) and the Gathering Years (1989-1995)

The Boss Years as I indicated were made possible by his connection to the FBI. Whitey had been opened as an FBI informant on May 13, 1971 by Agent Dennis Condon. This was during the Killeen/Mullins gang war.  Billy O’Sullivan and Whitey were the two big gunmen in the Killeen gang. O’Sullivan, the father of six kids, was gunned down around midnight by three of the Mullins in Savin Hill on March 28, 1971.  This was allegedly in retribution for O’Sullivan having killed Donald McGonagle in November of 1969. Whitey was also thought to have been with O’Sullivan when McGonagle was killed.

I’d surmise that when Whitey saw his fellow enforcer for the Killeens had gone  down, he figured it was time for him to seek out some additional protection.  He probably sought out Condon to feel him out. Later when the danger passed or he felt more in control, he walked away from him. Four months later Condon closed him out. Also closed out, but still carried as an informant by Condon and his partner Agent Paul Rico was Stevie Flemmi who was hiding up in Montreal.

During this time both Rico and Condon were looking ahead to getting out of the FBI business so they needed to pass Stevie on to another agent. There were none in Boston who they figured would be a good fit for Stevie. In New York they knew there was a young agent from South Boston who they thought might fit the bill. They had to figure out how to bring him back to Boston.

Working with Stevie they set up Frankie Salemme who was living in New York City and who like Stevie was on the lam for indictments against him for killing one of the Bennet brothers and blowing up lawyer John Fitzgerald’s automobile. Connolly “bumped into him” walking down Third Avenue and arrested him. In 1973 Salemme was returned to Boston and Connolly came back a short time later.

It was then arranged that the witness who could tie Stevie into the bombing and murder would get out of town for a while. Stevie was told to come back in May 1974. He did and rejoined his old buddies the Martorano brothers who were then with Howie at Winter Hill. He’d find a new member there, Whitey Bulger.

Within six months all the charges against Stevie were dismissed and he was passed on to Connolly.  A little over a year later, Stevie would have convinced Whitey that he too could get on the gravy trail by becoming an FBI informant. On September 18, 1975, Whitey signed on with Connolly.

Much of this was going on outside of public view. It’s difficult to know how much the other members of Winter Hill resented the growing friendship between Stevie and Whitey. They acted as if they were  totally oblivious that they were teamed up with the FBI even though Martorano alleged Whitey told him Connolly was going to feed him inside information. It didn’t seem to bother them that of the seven leaders of Winter Hill who were equally involved in the Race Fix matter only five of them were indicted. It doesn’t say much for their collective mentality.

The Boss Years were made possible by the FBI and it was during that time that the FBI worked closely to ensure that Whitey and Stevie were well protected and also that the most egregious murders were committed, those beyond the pale of normal gangster-on-gangster type killings. When I examine those years more closely I’ll be able to better judge the validity of Whitey’s reputation.

The Gathering Years are the years when Whitey having sown his evil sits back and gathers in the results of his efforts. He’s made most of his money. He’s moving it around in varying locations in the U.S. and Canada. He seems to have gotten out of the murder business.  It was appropriate he’d have stopped doing the active murders after all he’s gone through six decades of living and is into his seventh. Moreover, it wasn’t necessary for him to do any heavy lifting.  He had his right hand man Kevin Weeks available for the strong-arm stuff.

These were also the years when Whitey lost his FBI protection, John Connolly retired in late 1990; DEA had pretty much destroyed his drug operations in South Boston; Whitey won a share of the state lottery; the Boston Globe had pretty much indicated he was an FBI informant; Stevie Flemmi started hanging around more with Frank Salemme who had been released from Walpole prison after serving 16 years, and Fred Wyshak was starting to do his probe into his past activities.

I don’t expect I’ll find much to enhance his reputation in the Gathering Years, but it remains to be seen.