(This was written as part of the series to show that Whitey could have immunity despite being an informant. Judge Stearns as we know has ruled out much of his defense which Stearns notes is really not a “defense” but a bar to prosecution. Stearns wrote: “an immunity agreement cannot as a matter of public policy license future criminal conduct.” I suggest otherwise. I believe Judge Stearns focused too narrowly on the immunity issue as having been provided for information. I wrote this part of the series prior to his decision. It demonstrates a situation wherein such an agreement would be proper and AUSA Jeremiah O’Sullivan would have the authority to make a deal with Whitey.)
To determine what would motivate O’Sullivan to give Whitey immunity, we have to assume that O’Sullivan met with Whitey as Connolly and Whitey assert. We have to go back to that time to see what was going on in O’Sullivan’s and Whitey’s lives. Are there any circumstances that could have prompted O’Sullivan to so act? I set the time of the first meeting as December 1977 from an interview Agent Connolly gave to TA English. There may have been other meetings. For O’Sullivan to meet with Whitey he’d have to have a really compelling reason..
O’Sullivan at that time was getting ready to prosecute the Race Fixing case. He has good evidence that could bring about the conviction of Whitey and Stevie Flemmi in that case. However if they deal with him, he will give them a pass. He needed Stevie in the investigation of Gerry Angiulo’s Mafia gang which was one of the highest priorities of the Department of Justice and FBI in their war against the Mafia.
Prior to this time we know Flemmi had been a long-term informant for the FBI. Unlike Whitey, he admitted informing for them over 25 years. I’ve shown it was most likely Flemmi brought Whitey to meet with Connolly after they began to work together in the Winter Hill gang. It was Flemmi who was the main source of Mafia information for the FBI. In the late ’70s Flemmi had Mafia connections but Whitey had practically none.
Whitey was doing quite fine when O’Sullivan approached him. He was nearly finished consolidating his power over the Winter Hill Gang. The whole operation would soon belong to him and Stevie Flemmi. Whitey had eliminated his Southie competitors. Howie Winter the boss of Winter Hill was under indictment and he’d soon be incarcerated, if that didn’t happen, Winter, and the rest of the partners would be indicted for race fixing and put out of action. All the proceeds of the operation would soon flow back to Whitey and Stevie.
Whitey had no incentive to do anything else other than continue his operation in Somerville. If it got too hot there, then if he’d move anywhere it would be back to his home base in South Boston. O’Sullivan needed him to do something different.
O’Sullivan was dependent upon the information he was getting from Stevie about the Mafia. He knew that the closer he could get Stevie to the Mafia the more information he would be able to get. O’Sullivan needed a big favor. In return he was going to cut them out of the race fixing case.
He wanted them to move their office from the safety of Somerville to the Mafia’s turf in the North End. This way he could get Flemmi in closer contact with the Mafia. The Mafia guys never wanted to do any business outside their home turf — they felt safe only in the North End where they knew everyone who should be known.
Whitey would have been totally against this. He never wanted anything to do with the Mafia. There was an ancient distrust between the North End and Southie and a basic dislike for each other. The in-town Italian gangsters didn’t like the Irish gangsters and their dislike was thrown back at them in spades. Whitey knew they’d have no loyalty to an Irish guy and would give him up or set him up on some murder or another without a second thought. He’d finally got to be boss of his own operation and now O’Sullivan was proposing that he walk into the lion’s den.
O’Sullivan would know he had to do something to assuage Whitey’s fears and overcome his opposition. He needed him to move but he also recognized the danger he was putting Whitey in with the move. To get Whitey to do this so he could put Flemmi in a better position, giving him a pass on the race fix case was not going to be enough. He had to promised him that he’d protect him. He had to assure him if he cooperated he would grant him immunity for any future acts that he might be charged with as a result of the move, including murders, on the assumption the Mafia would set him up so that it looked like he had done one or several.
O’Sullivan wanted Whitey to move his operation into the North End, stay involved with Flemmi, and get him closely involved with Angiulo’s gang. Whitey was too smart and wary ever to have gone into the lion’s den without such a promise.
Unlike what Judge Stearns ruled, O’Sullivan did have the power and authorization to make such a deal. It was not “a license to kill” but a guaranteed protection against accusations of murder by Mafia types. O’Sullivan and Whitey knew putting him in daily contact with the likes of Larry Baione and Nick Angiulo on their home turf was putting Whitey at great risk. Whitey would well remember the time two of the South Boston Gustin gang leaders went to the North End for a sit down with the Mafia and came back in a hearse.
The deal proved well worth it because it helped bring down the Boston Mafia again and again. It also caused Whitey no deal of headaches. It exposed him to additional dangers as we’ve seen with the Lancaster Garage case where the state police discovered his operation.
This may not have been the exact quid pro quo between O’Sullivan and Whitey, if one existed in fact. It does show however that Whitey could render a greater service to O’Sullivan than just be an informant. It does give O’Sullivan a solid basis for offering to protect him if he agreed to take this treacherous course. Putting his life on the line to help O’Sullivan would certainly merit substantial assurances by O’Sullivan back to Whitey.
Whitey was never a big deal in and of himself. He was a nobody until he teamed up with Flemmi. Flemmi was the guy the FBI wanted. He was the guy who would provide them with information in 1981 to take down Gerry Angiulo’s Mafia operation and then in the mid-80s to electronically bug Vinny Ferrara’s Mafia operation at Vanessa’s Café in the Prudential Center and the information in the late ‘90s to do the bug on the Mafia induction ceremony and destroy the remnants of the Patriarca family.
It seemed Whitey’s job consisted of keeping the lines of communication open between Stevie Flemmi and the FBI. He could very well have done this without being an informant. The services he provided outside of giving information proved highly beneficial to O’Sullivan, the FBI and the US government.