§30: Re-Examining Whitey Bulger: The Learning Years: Training John Connolly

People who have written books suggest the reason Rico and Condon picked Connolly to arrest Salemme and to bring him back to the Boston FBI office was because of the South Boston connection, especially the Old Harbor Village link that Connolly had with Whitey. That doesn’t work. As far as the FBI is concerned in 1973 Whitey is pretty much an unknown. He’s not an FBI informant. He is  certainly not a player that the FBI would look to help it in its war to topple the Mafia.

What’s Whitey doing in 1973? He’s busy protecting his back in Southie and trying to get along in Winter Hill while attending to his gaming business. There’s an FBI report filed by Condon that states: “Informant advised that James Whitey Bulger has been moving around the city pressuring bookmakers and shylocks for payments of money. Bulger was told that he was coming on too strong and is going to curtail these activities in the future.”

Condon had a dalliance with Whitey during the Mullen-Killeen dust-up in 1971 but that was a local gang war with no Mafia connections. The FBI’s highest priority set by J.Edgar Hoover and his successors was to get the Mafia.  Whitey couldn’t help.

My take on this memo is Condon knew Whitey because that prior relationship when Whitey considering his options ran to him for help. Condon had picked up information from other agents about what was happening on the street and one thing was that Whitey was doing the strong-arm stuff. This coincides with what John Martorano stated. He said that Whitey had made a proposal to Winter Hill that they go around to all the bookies, pull some strong-arm stuff on them, wait to see if the North End shows up to complain, and if it doesn’t, then they’ll know the bookie is independent and they can take him for themselves.

Condon reached out again to Whitey using this information in an attempt to ingratiate himself with him, perhaps to see if he could flip him and bring him back on the team. Whitey didn’t bite. Condon then gave him the FBI line that  he couldn’t protect him and unless he he’d curtail his actions he was coming after him. Whitey yessed him, and thanked him, told him that he’d stop doing it, and went on his way doing as he always had done.

That’s the only mention of Whitey in the FBI files during this time. Whitey’s looked upon as a local bookmaker and leg breaker. He’s a  local police problem and not the feds. Sure they’d be glad to get intelligence from him about what was going on out on the street but he was of relatively low priority in the FBI’s war against the nationwide Mafia. The FBI did not do the local gang wars as shown by its absence when dozens were murdered in the Irish Gang War of the Sixties..

As best I can tell there are no reports from Connolly about Whitey until after he brings him in officially as an informant in September 1975. That makes two years Connolly is in Boston without any contact to Whitey. Doesn’t that seem strange if he had a “housing project” relationship and was so close to the Bulgers? If he was such a hot shot, brought back because of his Southie connection with Whitey, why did he wait two years to approach him? I’d have thought if this was a well planned operation the FBI would have wanted to have Whitey on board before Stevie came back to town.

There were so many different ways things that could have turned out that to suggest the way they did turn out was the only way things could have happened is to close one’s eyes to reality.  Here, because Connolly ended up handling Stevie and Whitey in 1975 we’re supposed to believe that was a planned over three years earlier in 1972. If only the FBI were that good!

There’s too much Monday morning quarterbacking in reconstructing these events. People write as if what happened had to happen without looking at the events at the time they are happening and realizing all the variables that existed. We must examine what was known a the time things were happening.

Connolly wasn’t brought back to Boston to handle Stevie. Stevie was still under indictment. His cases had yet to be fixed and he could end up doing the same time Salemme did, 18 years.. He wasn’t brought back to Boston handle Whitey. Whitey wasn’t an informant at the time. No one knew if he’d become one. He got back here through his connections. Everyone in the FBI and many outside know for an FBI agent from parochial Boston, “there’s no place like home.”

Salemme testified he recalled being flown back from New York to Boston in late 1972 under guard in the plane and thinking he’d rather be anywhere on earth rather than there. Connolly would fly back from New York shortly after him in 1973 thinking there was no other place on earth where he’d rather be.  They’d meet again in the Prudential Center in Boston 22 years later and again at Connolly’s trial in 2002.

What makes the most sense and what happened is that Condon, along with Rico who was in Miami, were trying to fix Flemmi’s cases. When they knew they had lined up their ducks and Flemmi could come home and get out on bail, they began looking for a handler for Flemmi. Prior to coming from New York Connolly had no knowledge in dealing with informants. He would not have had the chance to interact with any in his previous brief stops.

Condon was on the FBI’s Organized Crime Squad. So was John Morris who came to Boston in 1972. They commuted to work together. Connolly came in 1973 and joined that squad. Condon would have time to assess these men and others.

Condon would settle on Connolly and train him in the fine art of handling informants. When Stevie came back in May 1974 they’d slowly try to hook him up with Connolly. Passing informants on is a difficult business, the informant never trusts a follow-up FBI agent as much as the original one. It’d take several months before they’d become comfortable.