Stevie Flemmi was on board as an informant. Whitey wasn’t. To understand why Stevie needs to bring Whitey in it is good to take a look at how both men were being perceived by the Winter Hill Gang. John Martorano gave us an insight into their relationship with the others in that gang.
What he tells us corroborates my take that they were outsiders who jelled with each other and were standoffish with the others. Martorano tells that when Stevie came back from Montreal he “seemed different, more serious. And preoccupied — sometimes he’d be sitting in a room with the others, and they’d even notice that he was just staring off into space, and hadn’t said a word for a half hour. Yet he and Whitey somehow seemed to hit it off. They were the two Hill guys who were actually from Boston, the city itself.”
John Martorano went on a few sentences later, “Whitey and Stevie had more in common than their propensity for sudden violence. Unlike everyone else in the gang, member and associates alike, they barely drank. They didn’t smoke. Stevie was into . . . health food. . . . [Stevie] hated shaking hands with anyone. Whitey was the same way.”
Stevie and Whitey had become fast friends drifting away from the others. To cement the friendship Stevie needed to bring Whitey into the FBI fold. He would have to introduce him to his new handler, John Connolly.
Stevie had been Paul Rico’s informant. When Rico left Boston in 1970 he switched over worked with Agent Dennis Condon who made his return to Boston possible by guaranteeing he’d get bail on a murder charge in Suffolk County, an assault to murder in Middlesex, and a federal fugitive from justice charge. Stevie would see the FBI’s and Condon’s magic when all of those charges were dismissed within six months of his return in May 1974.
I’d suggest Stevie was never that comfortable with with Connolly. Rico and Condon were old timers who knew their way around. Connolly was a new kid. Stevie very likely was his first informant.
I’m sure Rico and Condon assured him that although they were leaving the Bureau they still had their contacts there to protect him. But because he had already built up a trust with the FBI and having had Condon vouched for him, he agreed to work with Connolly. He really had no choice. He was comforted by the idea he could commit crime with impunity guaranteed by the FBI. It’s difficult to wean oneself away from that type of teat.
Whitey had become close to Stevie. To Whitey, Connolly was a stranger despite what you may have heard of from others. Both came from Old Harbor Village but neither man knew each other back in those days as I’ve shown. Whitey’s about 46, Connolly 35.
I don’t want to be misunderstood. I’m not suggesting that the housing project connection had nothing to do with Whitey’s eventual relationship with Connolly. I merely suggest that it wasn’t what brought them together. It was Stevie.
That Connolly was from the project made it easier. The project does create a bond. I tell the story about going to visit a woman friend in a high government position. A tough looking, body guard-type guy at the door gave me the cold shoulder. He brusquely said my friend could not be disturbed. He all but told me to get lost and not to come back without a prior appointment.
I recognized him. When he finished giving me the brush off I said: “Aren’t you G . . . G. . . from Old Harbor Village?” I told him I remembered him because I lived there and watched him play football at the park. He lit up with a big smile. I was sitting with my friend in five minutes.
So there is a bond that will open a door but it only goes so far. Whitey telling FBI SAC Sarhatt of a close feeling towards Connolly because they grew up on the same neighborhood would make sense. That would account for his going along with agreeing to a meeting with Connolly.
By September 1975, the triumverate was established. It would operate as part of Winter Hill for a while but as a separate part of it. Over time because of the project and the South Boston Irish background Connolly would become closer to Whitey.
Yet the big question remains, how was it that Whitey was first told by Stevie about his relationship with the FBI.