§33: The Coming Together Conditions: [Re-Examining Whitey Bulger: The Learning Years:]

Outside Marshall Motors With The Winter Hill Gang Meeting Inside

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.





10 replies on “§33: The Coming Together Conditions: [Re-Examining Whitey Bulger: The Learning Years:]”

  1. Very good posts, great food for thought. Matt, what do you think of the possibility of a link between Whitey and the Gardner developments? I know that nothing suggests that, but I was wondering what you thought about any possible connection. On a side note…. we all know, in retrospect, prettymuch how, why, and when the many investigations failed against them over the years, but as former agent Connelly loosely put it, “If these two got hit by a Dudley, Winter Hill would be out of business.” I believe he used a different term, but he was essentially correct. To me, the obvious question is why no one ever really tried to make a move on either one or both of them…. they were so accessible,… and after a certain point rumors were rampant. Looking back over the body of work as a whole…..in my opinion red flags were everywhere.

    1. Rather Not:
      If Whitey could help out with the Gardner robbery the feds would be telling us the indictments were all a big mistake. You know the priorities in these things — nothing is more important than getting back the art work. When Myles Connor was jammed in for having in his possession stolen Andrew Wyeth paintings and trying to fence them to an undercover FBI agent he was looking at big time. Being a wise guy, like all the guys in this saga surrounding Whitey, he knew his only hope for getting good deal for himself was getting another painting. He stole one from the Art Museum in Boston and then turned it in for a sweet deal. If Whitey had the information on Gardner he’d have bargained with it by now (or at least Flemmi would have done so).
      As far as people making a move against Winter Hill as a whole, Gerry O’Sullivan went after the whole crew back in 1979 but gave a pass to Whitey and Stevie. That effectively ended the Winter Hill group. Whitey and Stevie then had what was left and thy didn’t stay in Winter Hill too much longer. The MA state police went after them in 1980 with an electronic bug; DEA,the Quincy police and others chased them down in the early to mid-eighties. Whitey seemed to be a step ahead of them. It was his discipline, also his and Flemmi’s source in the State Police (Dick Schneiderhan), and the FBI who helped them avoid getting caught. Red flags were all around — Whitey was well known as a criminal (not a murderer) involved in gambling and extortion and later on in perhaps in drugs. If there was money to be made, Whitey was there. But if the FBI has not only a hands off policy but a desire to protect him it is pretty tough bringing him in.

  2. so I read your book I always wonder who was the 3rd or 4 guy that Connolly got for the guild st. ceremony affadavite. you made it seem like it was st. Laurent but if salemmi DeLuca and others were prizy to the paper work from court he would have never been back on the streets of rhode island making money and ordering some guys to kill DeLuca around 2005-06. the saint went down hard and his family so he must have had been clean from the fbi informants around boston its strange, now I read its DeLuca taking the stand against bulger. I wonder how many hits DeLuca got under his belt, guys in his 60tys ran r.i. for 30 yrs crazy, today in the paper mark rosette got 12 yrs state time concurrent with the other bids. and the the fbi knows who did the gardner heist but wont release the names, im guessing there all dead.

    1. Pat mac:
      Thanks for reading the book. At Connolly’s trial they openly identified three of the informants for the Guild Street affidavit. Whitey, Stevie and Mercurio were identified. The identity of the other two was concealed except they were called D and E. I may have had the impression it was St. Laurent because of the way Judge Wolf testified. Look at how long Flemmi was an informant and I’s sure some had suspicions but without pretty good proof the wise guys usually won’t go after the person. St. Laurent from something I read wanted Bobby DeLuca whacked becasue he was going around saying St. Laurent was an informant.
      I doubt DeLuca will testify against Whitey although I did read “Meanwhile, Robert DeLuca, a notorious captain from Rhode Island, has disappeared from the area and is widely reported to be cooperating with authorities against his fellow made members.”
      I don’t see what he brings to the table. The last thing the prosecutors need is more gangsters coming in to testify. Next the rumors will be that the prosecutors plan to dig up John Gotti and offer him as an exhibit.
      The FBI was unable to help out Rossetti but it was not for want of trying. It will probably come through for him after the heat dies down.
      You don’t believe the FBI knows who did the robbery It sound like that typical FBI looking for lots of publicity for nothing. I could tell you I know the other guy who was with Lee Harvey Oswald when he murdered Jack Kennedy but prefer not to tell you. Would you buy it. It reminds me of a local police department that had a big stamp marked “SOLVED.” Whenever they arrested a person they’d stamp that on the file. It didn’t matter whether the person was convicted or not, once arrested they considered it solve.

  3. i would venture a guess that whitey was told about stevi and his fbi relationship when whitey asked stevi about how it was he came back from canada after being away for 5 years.look at how steve flemi was able to get out of legal trouble over the years due to his relationship with the fbi. counter that with jackie s and his non relationship with the fbi and how many yaers he spent in prison. i have always been surprised that jackie s did not have stevi killed. if anyone deserved killing it is steve flemi. regards,

    1. Norwood:
      Sometimes the gangsters aren’t as smart as they pretend. That they never figured Stevie was an informant is astonishing. I guess they became smarter in their later years. Maybe after the got involved with their lawyers. In this case it seems they have at least outsmarted the prosecutors considering the deals they made for themselves to give up Whitey whose actions were really hardly as bad as those of the others. Flemmi is really the bottom of the barrell. I think in his close association with Whitey that Whitey figured out what he was doing and put it on him. By that time they had become inseparable so Whitey let it be.

  4. Rico and Connolly were two innocent FBI agents. They were the most effective Law Enforcement officials against the Mafia in this region. Yet decades after they retire they are subjected to a smear campaign by the Mafia dupes in the media and Law Enforcement community. If you want to see how easy it is to frame an innocent person read Melville’s ” Billy Budd”. U.S. Att. Stern and Wolf convened a Drumhead Court Martial to get them. 2. How does Stern justify his deal with Salemme? Salemme is the head of the N.E. Mafia, the largest suppliers of Heroin. Why were Stern the DEA and State Police uninterested in finding out about this drug cartel? Why have a DEA if they won’t investigate hard drugs? Thousands of New Englanders have died in this trade. What a corrupt bargain, a sweetheart deal for the number one criminal in the area and minimal information in return. 3. Has the deal already been arranged to let WB win his immunity motion? Is the law professor the first in a line of experts to opine that the law requires immunity in this case? Casper allows the motion reluctantly but orders compensation for the victims. The case is closed WB is sent off to L.A. and no further investigation into the unpleasantness at Moakley Courthouse occurs. All go home happy save WB.

    1. Neal:
      1. You reemphasize an excellent point. It is true that the New England Mafia (Patriaca Family and its successors) were destroyed in main part by the activities of Rico and Connolly. No one seems to put into this equation the concept of revenge by the Mafia. Remember the Sicilian saying: revenge is best served cold. In the real world that should very much have been a calculus in this matter.
      2. There is no way Stern can justify the deal he made with Salemme who was a Mafia family leader who said he would not testify against anything the Mafia had done but only about Connolly and Whitey. It sort of shocking especially when they let him walk by reducing a perjury charge to something less. One could make a good case, as you seem to suggest, that the Mafia took over the prosecution of the its two worst enemies. Only with naive dupes.
      3. The best way to wrap this up is to quickly bring Whitey to trial and send him off to ADX Florence. No more deals. The books have been written. The prosecutors and FBI and judges will close the books. And they hope things will go on and people will forget. They won’t. As we examine this more closely we see that the prosecutors have been the tools of the gangsters just like Connolly became Whitey’s toy.

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