Prosecutor Wyshak and his team want him to be one because their interest was not just in prosecuting Whitey because if that were the case they could have taken his plea proposal; it was in demeaning, belittling and destroying every bit of his reputation. It was also to make Martorano, Weeks, Salemme and other criminals feel better. Their only rationale for violating the honor code of a stand-up criminal is to fall back on the idea “you can’t rat on a rat.” If Whitey was not a rat then they clearly are. Flemmi, of course, is king of the rats. All of this mandated that the prosecutors stick to the idea that Whitey had to be an informant.
They do not see the contradiction in their stance. They prosecuted FBI Agent John Connolly as a “rogue agent.” They said he was on the payroll of Whitey. That would mean information was not coming from Whitey but going to him. They are trying to have us believe not only was Whitey paying large sums to Connolly he was also furnishing him information. That makes no sense.
The prosecutors also fail to recognize another problem with their Connolly is a “a rogue agent” theory. If that were the case he could easily have set up a fake informant file for Whitey. He would want to cover himself for his many meetings with Whitey.
Here’s my take on it.
Whitey never knew Connolly existed until he met him sometime after Connolly became an FBI agent and came to Boston in 1973. The stories of their relationship during the time they lived in Old Harbor Village are the products of ignorant minds who had no idea of what it was like to live there at that time. Whitey had a reputation from his days in the project among all us little kids as one to avoid.
He went off to the Air Force and then to prison. When he came back in 1965 after trying to go straight he got back in with the easy money with the South Boston Killeen gang in the late 1960s. We saw in 1971 FBI Agent Dennis Condon opened a file on him as an informant which he wasn’t. Whitey would move over to Winter Hill in late 1972.
Connolly sometime after coming in 1973 would have learned about the Killeen/Mullin battle and Whitey’s role in it. At some place like the L Street Bathhouse or some gathering such as a wedding in Southie he would have run into him. He would have struck up a conversation. Both having lived in Old Harbor Village would have made the meeting easy and given them lots to talk about.
I’ve told how I once went in to see a judge. I recognized the court officer protecting her chambers as GG. Initially I said nothing. He was trying to shoo me away saying I needed an appointment. I then pulled out my ace and said, “Aren’t you GG from Old Harbor?” After that he could not have been nicer. Having grown up in the same project as each other would have produced a closeness between them.
Connolly had already been handling Flemmi. He’d have known Whitey and Flemmi associated with each other. Whitey has a big reputation in Southie. Connolly figured having him along with Flemmi as an informant would add to his creds in the FBI. They become friendly and start palling around together. Without Whitey knowing it, Connolly opens a file on him like Condon had done previously.
He starts putting into Whitey’s file information given to him by Whitey that amounts to nothing more than bits and pieces from general conversations or gossip. An example would be the report that the Norfolk DA having a vendetta against Whitey.
Whitey provides Connolly nothing of value, To keep up the pretense he is a valuable informant Connolly puts in his file things he is learning from Flemmi and attributing them to Whitey. Or he is taking things from other files about Southie and putting them into Whitey’s file.
Why is Connolly doing this? I’d suggest he recognized the growing relationship between Whitey and Stevie and in order to protect Stevie as a source he had to make himself part of the relationship. That also required him to make Whitey an informant so he could remain in contact with him and no one on his job would question it.
Keep in mind, Connolly never would have imagined that the FBI would admit Whitey was an informant or had a file. Even when Agents Morris and Fitzpatrick violated the FBI’s promise of secrecy by disclosing to the Boston Globe that Whitey was an informant, it carried no weight. Whitey was able to pass it off as an attempt by the Globe to impugn the integrity of his brother.
The FBI itself had reason to believe Whitey was not an informant. He denied being one when he met with ASAC Robert Fitzpatrick. During a four-hour sit down with the Special Agent in Charge Sarhatt it became clear he was giving information that was of little value. He considered terminating him.
Connolly because of this friendship and the need to protect Flemmi does everything he can to keep Whitey on the street. He feeds both of them information to keep them safe which is what the handler of a Top Echelon Informants (TE) is supposed to do. Not only is the handlers supposed to do that but everyone in the FBI is supposed to help him keep the TE informant on the street.
Connolly looks upon Whitey as a buddy, another Southie guy, and someone who will make his dealings with Flemmi easier. He labels him an informant to keep up his relationship. He tried hard to justify keeping him as a TE informant.
Whitey likes the idea he will get a heads up from Connolly who has become his friend. Whitey likes thinking of himself as a “good bad guy.” He finds he is accepted by not only Connolly but other FBI agents. He socialized with some of them. Connolly will keep looking out for Whitey’s interests. Connolly gets from it the reputation and freedom in the FBI as big time TE informant handler and the assurance Flemmi will keep providing the information.
Unfortunately, the Whitey Informant file would see the light of day. But even with that there would be a darker side to all of this.