§26: Re-Examining Whitey Bulger: The Learning Years: When Stevie Met Whitey

Quincy Police OC Unit’s Picture
Of Whitey and Stevie Meeting

All the books written about Whitey and Stevie Flemmi jump over the return of Stevie and his involvement with Winter Hill. None seemed to be curious about how Stevie and Whitey became partners. They treat this happening as if their relationship had existed for all time, yet as we know Stevie had no knowledge of who Whitey was prior to his return, nor did Whitey know much about Stevie except from what he may have learned from the others.

I suggest it is important to understand how they became partners in order to understand how it was they developed their relationship within the Winter Hill Gang and with FBI Agent John Connolly.

The reason the books are lacking information about this is that Stevie did not testify about it. Had Stevie done so then we may have read something about it but what we would have read is what Stevie told us. We know Stevie is a liar so how do we construct our knowledge or put much credence in what he says one way or the other. Stevie, like all the others who turned state’s evidence, knew the best chance for a sweetheart deal was to lessen his involvement in crimes while exaggerating the importance of Whitey. That is what the prosecutors wanted to hear.

In the middle of 1974 outside of South Boston Whitey is a nobody. When you read Ralph Ranalli writing that states around March 1973 Whitey was “either involved in or ordered seven other murders during the same time period according to Martorano’s plea agreement” you see how much loose writing has occurred with respect to this matter and how little it has been examined. At that time Whitey is in no position to order anyone to do anything, he’s pretty much a supplicant.

In South Boston he still exists in a precarious position. He has formidable enemies in the Mullen Gang including Paulie McGonagle who is still smarting over the death of his brother at the hands of Whitey’s friend Billy O’Sullivan; Tommy King who is reputed to be as smart and tough as Whitey who wasn’t happy with the deal cutting Whitey in on the South Boston rackets when it looked like he was on the run and they could have had it all for themselves; and the ever treacherous and wily Pat Nee who had made the truce with Whitey. Nee was probably the most dangerous and conniving of the three having been trained as a Marine grunt and having served in Vietnam. Although he probably was not the toughest.

We’ve seen Flemmi was in continual contact with FBI Agents Rico and Condon during this period of time making sure things were going as planned. He must have had some contact with the Winter Hill Gang probably through one of the Martoranos who were with him as part of the Roxbury Gang. He had no prior relationship with Whitey to speak of. Judge Wolf wrote in his opinion that “Bulger and Flemmi had met socially once or twice in the 1960s, but did not really know each other previously.” It’s difficult to see that even happening since they ran in different world’s and half that time Whitey was in prison.

Here are the things that happened during this time that we must try to figure out before we go on. How did Stevie and Whitey become bosom buddies? What was their relationship to the rest of the Winter Hill Gang?  How did they both end up as FBI informants?

When Stevie gets back, he and Whitey seemed to be drawn to each other. Whitey is still an outsider in the Winter Hill Gang, he’s accepted but considered a little bit different. I’ve noticed over and over again a trend that people never seemed to warm up to Whitey and would knock him behind his back but no one ever did to his face. I’d suggest the Winter Hill gangsters at the time had a lot of respect for Whitey, if not some fear of him, but considered him somewhat of, not so much a loose cannon but, a loner who walked to a different drummer.

Stevie would have to renew his old acquaintance with John Martorano and his brother Jimmy, part of the Roxbury Gang. Almost five years had passed since they had done anything together. Prior to his flight, Stevie was working with Frankie Salemme and Larry Baione and did very little with John Martorano. If they weren’t that close, the passing years would have not brought them any closer. It’s likely they had little left in common.

There’s no reason to believe Stevie had a close prior relationship with Howie Winter, Joe McDonald and Jimmy Sims. He ended up on their side during the Boston Irish Gang War but he began on the side with the McLaughlins and his involvement was not so much as part of either side but doing some killings with Frankie Salemme who was working for Raymond L.S. Patriarca.

So in a sense, like Whitey he too was somewhat of an outsider in the group. Frankie Salemme  pretty much described the position they were in when when he testified in April 10, 2003, under a court issued immunity order. Although he was speaking of some other hoodlums the description sort of fits, “I like to call it the banding of the misfits, because they couldn’t hook on anywhere else, they hooked on with themselves and used to hang out together.”

Frankie Salemme gave further insight into this when he specifically spoke of Whitey and Stevie:  “Bulger was a squirrel, and so was Flemmi. They’re not extravagant people. They’re not nightlifers or boozers.  They weren’t gamblers and they didn’t do drugs . . . .”  He’d also called Flemmi a womanizer, a description some gave about Whitey.

What I suggest is you had two hardened criminals each of whom was as tough and fearless as the other. Each found in the other an image of himself. They had the same likes and habits. They needed some one person to totally trust. They knew the other top gangsters in the group already had strong allegiances to others.

They started to hang around with each other. Whitey liked it that Stevie had combat experience and was someone he could exchanged war stories with. The liking turned into a trust and then a partnership.

It seemed to happened very quickly, sort of like love at first sight. We know though that Flemmi had another very close relationship. We don’t know when he told Whitey about it but we do know that Whitey would learn of it. It would become a  ménage à trois minus the sex.


12 thoughts on Ҥ26: Re-Examining Whitey Bulger: The Learning Years: When Stevie Met Whitey

  1. Salemme stated that the only two things Flemmi was motivated by were women and money, “not necessarily in that order”. And, as you had mentioned, was not into using drugs, drinking in excess or partying. It seems many of thier colleagues, and in Flemmi’s case, sibling(s) were. The pleasure they derived from thier work most likely did not stem from having a good old time with the boys. Guys like Pat Nee probably did enjoy that aspect of being a gangster, and couldn’t relate or connect to either of them aside from the business they were involved in together. Salemme also mentioned that Flemmi was by no means a prolific planner and was very reactionary in his approach to business. Partnering with Whitey may have been a good move in that regard. And for Whitey, I would imagine partnering with Flemmi would have many benefits to include his relationship with LCN, fearsome reputation and abilities and status with Winter Hill.

    1. John:
      Everything indicates Flemmi and Whitey were part of Winter Hill but also not like the other guys. I have a quote from Martorano I’ll write about in a day or two. They were both motivated by women and money. Weeks called Flemmi a brilliant business man. He owned about a dozen or more properties in Boston and the surrounding towns when he was arrested. You’ll see how I put this together but basically it comes down to Flemmi needing Whitey in order to keep himself safe.

      1. Perhaps being an owner of that many enterprises, along with keeping up appearances with a wife and a mistress or two on the side, didn’t allow Flemmi much time to devote to planning murders and other apsects of OC. Between the Feds and Whitey, he had plenty of cover to pursue his interests.

        1. John:
          Take a look at Flemmi’s plea agreement to get a sense of how much property he owned (and how much he still has). You’re right on the button about him being a busy man. Despite all that he still murdered those young women so there is something definitely wrong with the man. The Debbie Davis case is particularly bothersome because she was his girlfriend for many years and apparently wanted to dump the old guy for someone closer to her age. You’d think with his supposed vaunted ability with women he’d have been grateful to her for having giving him the best years of her life. It takes a particularly cruel and psychotic man to do what he did to the Davis woman. I’m not that much in favor of the death penalty but I’d have little trouble pulling the switch on a guy like Flemmi who’d murder a young girl like he did.

          1. Yes, reading the agreement it shows that although he did forfeit some properties he was able to hold onto some as well. Many of them being Condos. With that amount of investment in RE, with its low liquidity, it again shows that Flemmi hadnt planned for his retirement the way Whitey had. Or, he was banking on the Feds bailing him out.

            1. John:
              Kid’s comments suggest Whitey was a step ahead of Flemmi. He stayed with liquid assets and Flemmi went and invested in real estate. That’s why Whitey could easily take off and Flemmi felt he had to stick around for a few more days to straighten things out. As to your last remark, I don’t think Flemmi ever thought he’d end up in jail. He’d been an informant since probably the mid-Fifties or early Sixties at the latest and nothing ever happened to him. When he was grabbed on the 1995 charges he still was reaching out to the FBI to help him out. I guess that explains why Flemmi felt he had gone legit and was investing in condos. Good point. That’d also show Whitey knew the feds would only go so far for him.

  2. I would speculate that Whitey must have known from the start about Flemmi’s relationship with the FBI. Those are pretty serious charges to beat just like that. Maybe all the other plug uglies buy the ol-lucky-that-the-witness-went-away-story from Flemmi, but bulger was smarter than that (and he did 12 years for bank robbery)… I wouldn’t be surprised if Whitey knew exactly what was going on, and knew others didn’t and proceeded accordingly.

    1. Kid:
      I don’t buy it that Whitey knew when Stevie was coming back that he was hooked in with the FBI. MArtorano writes that they thought Winter Hill was behind Daddieco not showing up (until he learned later it was the FBI) and they helped him take off so they could help Stevie. So Winter Hill took credit for his not being tried for those crimes so no suspicion attached to the failure of the state to prosecute Stevie. Over the next couple of days I hope to suggest how their partnership came about. You give Whitey a lot more credit than he deserves when it comes to knowing much about Flemmi before he met him.

      1. I’m not saying Whitey knew much about Flemmi before he met him, but just after they did meet. If Whitey sought out FBI Condon in 1971 to see if ‘protection’ was an option, it tells me he’s aware of the types of services one might count on the FBI for.. if you’re a murdering thug who knows other murdering thugs. My perception of Flemmi is that he’s not as sharp as Bulger. I picture Bulger connecting the dots through conversations he’d have with Flemmi… but you’re right. This is one aspect of the story that’s never been known. All we can do is speculate. Which makes me think there’s a pretty good reason for that.

        1. Kid:
          I got to say you’re right on the button with your comment. Salemme said over and over again that Stevie was not a planner. Everyone seems to indicate that Whitey was such a guy. In that sense Whitey was in a different league than Stevie. You’re right about what Whitey was looking for in 1971 and he knew that the FBI could bring something to the table for him. He spent 10 years in federal prison and talked to hundreds of guys and at a minimum knew how things operated on the outside and how the guys inside got screwed by some informants. Whitey was probably among the brilliant criminal minds. I’m still thinking it through but your suggestion that Bulger connected the dots is a good one since that was a sense I was coming to.
          We are doing more than speculating in our approach. What I are doing is eliminating things that I know do not make sense or could not have been. For instance, anyone who suggests Flemmi did not continue on as an informant after he came back to Boston is blowing smoke. When I eliminate things like that, as you also seem to be doing, then we can come to a pretty good conclusion about what happened.

          1. Flemmi seems to me to be the FBI’s MVP. not the brightest bulb on the tree but his ‘access’ trumped all, absolutely all. Partnering him up with Whitey made for a good 20 year run. Whitey’s skill set complemented Stevie’s ‘skill set’ and they were formidable together and made tons of cash. Keeping Stevie the pedophile on the street was good for FBI business. Is keeping Stevie happy still good for FBI business today? Is he still MVP? What kind of service award does a 50 year FBI man receive?

            1. Kid:
              Flemmi was the main man. Adding Whitey in on the team made Flemmi more secure and as they way, two minds are better than one. In a sense Flemmi was betrayed by the FBI because he was promised not to be prosecuted for information he gave the FBI which they used to go after him. Much of the information used to get his original RICO indictments came from wiretaps he helped them set up.
              His award was given to him in his deal with the prosecutors. Flemmi is a particularly evil man. He is the one who murdered two young women, one who he had molested since she was a child and the other who had been his girlfriend for many years from her teen age years. He’s the type of buy who should make your skin crawl if you come near him. The prosecutors saved him from going to the death chamber, did not require him to forfeit many of the properties he acquired with the money he earned from the rackets, and are now letting him live in relative comfort and may have a deal to let him hit the street again. That’s not a bad award for his services considering he should be sitting on death row wating to be strapped into an death chair. I don’t think thee is any other case in the history of America where a person (Martorano) who murdered two people by shooting them in the head in Florida and Oklahoma is out on the street; the guy who was his contact in Boston (Stevie Flemmi andother Charles Manson) who he admits he set up the murders is doing easy time and has kept much of his property; and a guy (Whitey) who committed less than half the murders these guys did is put up as the big bad guy.

Comments are closed.