There are things that point to Whitey being an informant. On the other side we have Whitey’s denial, the lack of corroboration outside of the 700 page file or the words of Steven Flemmi and his handler, Connolly.
A long time I go I tried to untie what I thought was the Gordian knot in the Whitey Saga. How did it happen that two guys, who as Martorano said would be endangering their lives were it known that they were informants by the others in the gang, get to know the other one was an FBI informant? Not one person has answered this to an objective observer’s satisfaction. One top-level criminal who is an informant does not walk up to another top-level criminal and say: “Hi, Sal, I’m an FBI informant do you want to become one too?”
Here is one thing we know for sure. Flemmi who was an FBI informant from around 1965 came back to Boston from Canada in 1974 at the behest of the FBI. It had fixed it that the two serious felony cases which caused him to flee back in 1969 were dismissed. The quid pro quo for that new lease on life was that he continue to be an FBI informant. He was their window into the Mafia before he fled and would be until 1990 when he was terminated.
When Flemmi rejoined Winter Hill in 1974 he will meet Whitey for the first time. At that time Whitey is not an informant for the FBI. Flemmi is. How does Flemmi make known to him that he is an informant for the FBI knowing that Whitey hated rats?
None of the authors come close to explaining it. Black Mass gives us the fiction of the Wollaston Beach meeting . It has everything backwards. It makes Whitey the first informant.
It then tries to explain how Flemmi became one. The authors are at a loss to do so. They slips over this conundrum by writing: “Bulger blended in Flemmi, and a package deal was done.” This is nonsense. One top level rat doesn’t “blend in” another top level gangster into becoming a rat. They had no answer to this critical piece of information so they just tried to blow it by the people.
Howie Carr’s book The Brothers Bulger written six years after Black Mass correctly notes that Flemmi after being brought back in 1974 went back to business as usual which meant “talking to the FBI.” Carr’s book correctly says, as I’ve pointed out, the beach meeting was fictitious. (His book wrongly has it at Carson Beach rather than Wollaston Beach. Earlier he put Salisbury Beach in New Hampshire. Apparently fat guys don’t go to the beach much.)
The question remains if Flemmi was already on board, how did Whitey sign up? Carr says Flemmi said Whitey approached him one day in 1974 and told him he was talking with the FBI. In 1974 they hardly knew each other. Do you think Whitey is going to walk up to Flemmi and just pass that off as if it is nothing? Then the book delves into nonsense saying that Whitey told Flemmi Connolly wanted to meet him.
Carr has already written that Flemmi is already an informant. What happened is that Flemmi’s handler Condon was retiring from the FBI. He had to get another FBI agent to handle him. He picked Connolly. He arranged for Connolly to be introduced to Flemmi in the Newton Coffee Shop. Whitey played no role in this.
Neither book which laid the groundwork for all subsequent stories has a grasp on how it was Flemmi told Whitey he was an informant. I have struggled with that because I could not come up with a scenario that really satisfied me. How would Flemmi tell Whitey he was an informant? Over time I worked several theories around in my head but none made sense.