Whitey: The Joe Berlinger Film: Whitey the Informant – The Gordian Knot

2015 11 29_3162There are things that point to Whitey being an informant. On the other side we have Whitey’s denial, the lack of corroboration outside of the 700 page file or the words of Steven Flemmi and his handler, Connolly.

A long time I go I tried to untie what I thought was the Gordian knot in the Whitey Saga. How did it happen that two guys, who as Martorano said would be endangering their lives were it known that they were informants by the others in the gang, get to know the other one was an FBI informant?  Not one person has answered this to an objective observer’s satisfaction. One top-level criminal who is an informant does not walk up to another top-level criminal and say: “Hi, Sal, I’m an FBI informant do you want to become one too?”

Here is one thing we know for sure. Flemmi who was an FBI informant from around 1965 came back to Boston from Canada in 1974 at the behest of the FBI. It had fixed it that the two serious felony cases which caused him to flee back in 1969 were dismissed. The quid pro quo for that new lease on life was that he continue to be an FBI informant. He was their window into the Mafia before he fled and would be until 1990 when he was terminated.

When Flemmi rejoined Winter Hill in 1974 he will meet Whitey for the first time. At that time Whitey is not an informant for the FBI. Flemmi is. How does Flemmi make known to him that he is an informant for the FBI knowing that Whitey hated rats?

None of the authors come close to explaining it. Black Mass gives us the fiction of the Wollaston Beach meeting . It has everything backwards. It makes Whitey the first informant.

It then tries to explain how Flemmi became one. The authors are at a loss to do so. They slips over this conundrum by writing: “Bulger blended in Flemmi, and a package deal was done.”  This is nonsense.  One top level rat doesn’t “blend in” another top level gangster into becoming a rat. They had no answer to this critical piece of information so they just tried  to blow it by the people.

Howie Carr’s book The Brothers Bulger written six years after Black Mass correctly notes that Flemmi after being brought back in 1974 went back to business as usual which meant “talking to the FBI.” Carr’s book correctly says, as I’ve pointed out, the beach meeting was fictitious. (His  book wrongly has it at Carson Beach rather than Wollaston Beach. Earlier he put Salisbury Beach in New Hampshire. Apparently fat guys don’t go to the beach much.)

The question remains if Flemmi was already on board, how did Whitey sign up? Carr says Flemmi said Whitey approached him one day in 1974 and told him he was talking with the FBI.  In 1974 they hardly knew each other. Do you think Whitey is going to walk up to Flemmi and just pass that off as if it is nothing? Then the book delves into nonsense saying that Whitey told Flemmi Connolly wanted to meet him.

Carr has already written that Flemmi is already an informant. What happened is that Flemmi’s handler Condon was retiring from the FBI. He had to get another FBI agent to handle him. He picked Connolly. He arranged for Connolly to be introduced to Flemmi in the Newton Coffee Shop. Whitey played no role in this.

Neither book which laid the groundwork for all subsequent stories has a grasp on how it was Flemmi told Whitey he was an informant. I have struggled with that because I could not come up with a scenario that really satisfied me. How would Flemmi tell Whitey he was an informant? Over time I worked several theories around in my head but none made sense.



  1. Maybe Whitey never was an informant….despite the dubious file. Connolly gained status, financial reward, and promotion by perpetuating the Whitey informant persona.
    Meanwhile Benji really is , and has been a rat, and comes home from his photographic sojourn in Montreal.
    Now, he’s back, and rapidly getting tight with our friend James over on Marshall St.
    Condon/Rico has an idea….
    Let’s use our recently gift-wrapped young superstar transfer Master Connolly to…..
    Condon takes several runs at James……
    Likewise Connolly…
    Then they create the file and the rest is history….James knows nothing of the file, or of his little partner’s Benji’s ties to Rico/Condon/Connolly on the books, but keeps “giving them shit (and cash)…and getting gold”

    Furthermore, this could explain why Benji was caught flatfooted when the indictments were coming down. The intended fall guy.

    • Rather:

      Close – there is no doubt that Whitey had no idea he had an informant file on him. Keep in mind he and Connolly were more than agent hander/gangster informant they became friends. They each used the other one for their own purposes. The chummier Connolly gets with Whitey the more he runs into him when he’s with Flemmi. He doesn’t worry because Flemmi’s already on the boat; Whitey doesn’t seem concerned since nothing he talking about with Connolly is anything more than general gossip. Everyone said that Whitey was the talker and Flemmi more of less just listened and thinking that “good old Jimmy, if he only knew how I had the inside track.”

      I don’t see Rico doing anything but telling Flemmi he can trust Condon – he’s out of here by 1970 and out of the FBI by 1975. Condon’s retiring in 1977 or thereabouts and he needs to turn Flemmi over to Connolly – no record of the transfer – not much record of Flemmi being a TE even though he was treated as one – one SAC noted that even though he has been closed we will continue to take his information – what a joke – but it was all kosher under the FBI’s TE program whose purpose was to keep guys like Stevie and Whitey on the street so they could get information on what was going on out there.

      Stevie got caught not because of any fall guy scenario it was that he thought he was better connected with what was happening in Boston than anyone else. He knew the indictments were coming down on the 11th. Neither Whitey, Salemme nor anyone else knew that. What he did not know were the arrest warrants were coming down on the 5th. Neither did Whitey who was on his way back to Boston or Salemme who got a call from his wife telling him the house was surrounded by federals. How did Stevie know about the 11th; Schneiderhan who idolized Flemmi as Connolly idolized Whitey had a niece who worked in the U.S. attorney’s office who must have kept him posted. She would not have known about the arrest warrants.

  2. Mtc. has long since passed the ” Theorizing ” portion of the Exam . His conclusions based on evidence, as seasoned he ceetainly is, should make people nervous. Passive Stevie whacked his underage love objects as was his … wont. He dod not stand by nursing his thumb while ” Ma Flemmi, that terrible Bulger man, Billy, whoops Ma … gettin’ ahead of the STORIES … Jimmy !!! …strangled my sweet doves and then fer’ chrissakes Ma … he took a snooze … Why Mama I had to mutilate, pull teeth, and dismember and bury my pets all by myself !!!!! … Yes Mama, that bastard actually strangled one of my girlfriends in your patch … just steps from the Senate President”s own home threshold !!!!!! ” …. YEP FOLKS … that is what we were all considered… such fools … that this wickedly poisonous dish was placed ” neath our noses ; and then we had our bibs placed on us, like so many dazed diners, and were encouraged to ….. ” CHOKE ON IT DUMMIES !!!!!! ”
    Dogged Matty don’t like this dish : He identified it as the poisonous mush that it is. He identified that the BIG GAME WAS BILLY. He has patiently built a case for one of the most malevolent and truly wicked character assassinations in history, Senate President Bulger’s, and he amply fulfills the Irish Creed of never forgetting or forgiving your enemies.
    So, Trek On Prosecutor … Roger that .

    • John:

      Sometimes you give me more credit than I deserve, note I said sometimes, usually you hold my feet to the fire until they burn.

  3. Richard baker is one of many of connolly sympathizers chiming in. Norwood born is not one of them. Not sure what that guys gripe is.

    • Matt,

      Why don’t you lay out the theories you’ve considered?

      I mean, summarise the elements of each theory and then the flaws that have caused you to discount it.

      It might save others “trekking toward the truth” from going down blind rabbit holes.

      In the process of articulating your abandoned theories and why you’ve abandoned them, you might gain fresh new insights and possible other ideas.

      Happens to me.

      Just a thought.

      As I’ve admitted already, I’m just a fool. Little else.

      Have mercy.

      Thanks, in advance.


      • Roger:

        Good point but as you point out I’m also a work in progress. The more I write about these things the more I try to fit them into place so that they make sense to me. I’m looking for feedback by people who find that I am off base and explain why they think so. I’m always willing to look at it another way. It is a trek for me but I started from such a low road having been infected with ideas by people with malice in their hearts that it takes a while to cleanse myself. But good advice.

    • Ernie:

      Baker was a former FBI agent and is in contact with Connolly. As all ex-FBI agents he is biased towared the FBI which is expected. Norwood is a regular guy who has lived in Florida, Hawaii, and other places but likes to check in on what is happening in Boston.

  4. Afterthought: Would be great if one or more of Connolly’s friends who read this blog would chime in with their thoughts about this situation. I’m definitely not a Connolly fan, but at the same time, I’m not buying into the ridiculous notion that he was some kind of “rogue” agent. He was doing just what the bureau wanted him to do. It’s infuriating to think that even the loathsome John Morris escaped punishment.

    • Dan:

      You are not a Connolly fan because he has been destroyed in the media. The Boston jury found him not responsible for the same thing the Florida jury found him responsible. He did what the FBI wanted him to do. The reason why others in the Bureau will not join in is because there are often posts here that have not to nice things to say about the FBI. Baker to his credit still stays around even though he does not like a lot what I say. Just read a book by Mark Felt (Deep Throat) who rightly points out the FBI never felt it was under the control of the US attorney general. It did and does what it wants to do. Its top echelon program that produced and protected Whitey and Stevie is an abomination.

      • Matt: It sounds to me like you want a foot in both camps. On the one hand, you’re defending Connolly by saying he was destroyed by the media, and that he was only following orders. On the other hand, you’re saying that Connolly developed a man-crush on a dangerous criminal who gave him nothing in return. You’re also saying that Connolly fabricated a 700-page informer file on Bulger, no? And you’re saying that Bulger didn’t know anything about it. How could he, since he wasn’t an informer?

        I’m not buying it. Bulger and Flemmi were as thick as thieves (which, as a matter of fact, they happened to be). They both knew exactly what was going on. They knew what Connolly expected of them, and what they expected Connolly to deliver in the way of protection. Why would Bulger become an informer? The answer is simple: He became an informer in exchange for a license to steal. And that’s exactly what happened.

        • Dan:

          Let me be clear. Connolly’s job was to protect his Top Echelon informants Whitey and Stevie were Top Echelon informants anointed as such by FBI headquarters. His job was to protect these people which meant keeping them on the street and by tipping them off about investigations aimed at them.

          Also in doing this job his relationship went from handler/informant to a friendship with Whitey. He came under Whitey’s mendacious influence giving him benefit of the doubt where he should have suspected him. This was a result of the “man crush” he had on him which allowed him to abet Whitey while believing he was still doing the job that he was supposed to do. It was in Connolly’s interest within the Bureau to be seen to have such high level informants as Stevie and Whitey.

          Whitey gave Connolly lots of stuff. Much is contained in the “informant file” that Connolly opened up on him. Whitey never knew about the file. Nor, do I believe Stevie knew a file was being kept on him. Whitey never thought he was informing when talking about things with Connolly; Connolly used the information that Whitey talked about and put it into the informant file even though much of it had little value or was deceptive. Whitey and Connolly spent lots of time together passing information back and forth as part of general conversations.

          Bulger and Flemmi were as thick as thieves which in fact both were. That does not mean they were treated the same way by Connolly. Connolly valued his friendship with Whitey and was motivated toward him differently than he was toward Flemmi. He could put the squeeze on Flemmi; he could not do it with Whitey. It happens when two people as thick as thieves each does some thing unknown to the others.

          • Matt: I guess we’ll have to agree to disagree. I think Connolly and Bulger were savvy enough to know what the other wanted. I agree it would have been crazy for Connolly (or any other FBI agent) to say, “Hey, I have opened an official FBI informant file on you.” But both men must have known the game they were playing, particularly since their relationship spanned many years.

            By the way, I think it was an arm of the U.S. government that destroyed John Connolly. I’d have to downgrade the media’s role to that of megaphone. At Bulger’s trial, Flemmi testified that he and Bulger had paid Connolly $230,000 in bribes over a 10-year period. I don’t know how Flemmi came up with this preposterous number. Maybe he thought “230,000” had a ring of authenticity. Flemmi also claimed that he and Bulger had given Connolly $50,000 from their end of a drug deal. So Connolly was not only corrupt, he was complicit in drug trafficking. I don’t know John Connolly from a hole in the wall, but I don’t believe he was complicit in drug trafficking, and I don’t believe he received hundreds of thousands of dollars from these two low lifes. But the government obviously had no such reservations about Flemmi’s testimony.

  5. Matt
    Why isnt it possible that while Flemmi was already an informant that he HAD to have brought Bulger into the mix? Why are we collectively ASSUMING that somehow Flemmi had something to do with bringing Bulger into the Top Echelon Program? Isnt it conceivable that Bulger was never an informant and simply paid for information from Morris and/or Connolly? Isnt it also conceivable that because of Connolly “man crush” on Bulger that Whitey played Connolly so that it seemed like wasnt a “rat” but simply using Connolly? But again its the whole PERKS that Bulger received from his relationship with Morris and Connolly that leads one to conclude he was probably an informant.

    What I am wrestling with is this: Is it possible that Bulger was able to corrupt Connolly, Morris, and O’Sullivan?

    • Jerome:

      Stay tuned. I think I answer your questions as I go along. Flemmi was as he admits always an informant. It is true that Bulger may not have been a TE informant except on the books; whether he paid for information or whether it was given because of the :man crush” Connolly would have had on him remains up in the air. Whitey was cheap – notoriously cheap – he loved and coveted money like many Americans. But Whitey and Flemmi had extensive time together with Connolly, they weren’t just commenting on the weather. Keep in mind Connnolly was a “big man” having Whitey as an informant so that has to figure in. Morris is sort of following along; he likes to associate with the tough guys and likes the wine and money they can give to him. He filed on reports and did not do any supervision of the relationship.

      When you ask if Bulger could corrupt Connolly and Morris you must be mindful that Connolly and Morris were doing what they were supposed to be doing which was to protect him. Many have written that in doing that they were corrupt, that is, in tipping them off to wiretaps they were corrupt. The argument against that is that to have a TE informant that is what they were supposed to do. If they are doing what the FBI headquarters tells them to do in relation to informants by whose standards do we call them corrupt. Sure, Morris took money but even he said at first he didn’t think that affected him; as for Connolly taking money, if he did it wasn’t anything near what Whitey said it was. Whitey was too cheap for that.

      As for O’Sullivan Bulger had nothing to do with him. I have serious doubts they ever met. It makes no sense. You have to prosecute these guys – I had to do it – you don’t want any kind of a relationship with them which will interfere with that. O’Sullivan corrupted himself because of his fear of the FBI.

  6. Hi Matt:
    I agree it’s a puzzle. One possible explanation is that Connolly brought them together since the two were already working in tandem as criminals. But did he actually do so, and if so, why? There are a lot that puzzles. John Morris made what I view as an attempt to have Bulger murdered by telling the Boston Globe that Bulger was an FBI informant. But, as you know, nothing happened. If I recall correctly, Kevin Weeks said the story was dismissed as newspaper bullshit. The Globe used a strange circumlocution, saying that Bulger had a “special relationship” with the FBI. Was this phrase the bright idea of a reporter, an editor, or something that was worked out in collaboration in Morris? Would things have been worse for Bulger if the Globe said flat out that the gangster was an informer? Don’t know the answer to that, either, though I think another gangster would have thought twice about taking Bulger on, even if Bulger was suspected of working for the FBI.

    • Dan:

      Connolly was often in the company of Stevie and Whitey but mostly Whitey. Stevie was already Connolly’s informant when Whitey started dealing with Connolly. It does not mean that when Whitey came along – through the project connection – he knew Stevie was an informant or that he was an informant. Waht complicates the matter is the “man crush” that Connolly had on Whitey.

      Whitey and Stevie did not know each other before late spring 1974. They did not hang around together exclusively until 1978 when Howie was imprisoned and Martorano fled. In the spring of 75 Connolly opens a file on Whitey so he had met him sometime before that. No reason for Stevie to tell Whitey he is an informant; from all I can see Connolly was not a demanding handler.
      Back in 1988 I was called by Kevin Cullen from the Globe. He asked me if I thought Whitey was an informant. I said no way. I read the “special relationship” story and it still never occurred to me that he was an informant. I knew nothing about the FBI top echelon program; I just had a gut feeling you don’t have top gangsters as informants so I believed the FBI would operate like I was doing.

      I must admit I’m surprised at reading State Police Colonel O’Donovan and others believed Whitey was an informant back in 1980. I believe there are reports to that effect back in those days. I knew O’Donovan and others who were in the OC investigating business and never heard anything about it back then.

      The Globe story had no legs because it was well known in Boston that it hated Billy Bulger so people would assume it was taking a whack at Whitey because of that. I don’t think it would have mattered if the Globe said straight out he was an informer judging from myself because I would not have believed it. Of course, by the time the article came out in 1988 almost all of the guys who would have taken a shot at Whitey were in prison and those not there in the Mafia were fighting among themselves. So even if someone believed it the question would be whether that person was capable of doing anything about it.

  7. Hi Matt and thanks for an interesting, well written article.

    Was Dennis Condon one of the FBI agents who persuaded Barboza to testify against the Mafia leaders such as Angiulo?

    What is your understanding of why Barboza turned on the Mafia?

    • Dfishwick- It came down to them mucking around with his bail, Rayomond The Man wouldn’t bail him out. When his friends tried to raise it for him they got it stolen and killed. Barboza went Bonkers, they were his closest friends.

    • David:

      Condon was with Rico when Barboza decided to be a witness.

      Barboza turned probably because he knew they had a contract out on him. He knew too much. The commonly believed story is that he did it because they murdered his friends who were raising bail money for him. That may be true but it had to be more and I think Condon and Rico convinced him he’d be dead if he did not get into the witness protection program.

  8. You’ve never regarded how participation in LSD experiments @ Leavenworth, which were part of MK-ULTRA, trained him operationally. He was leagues ahead of the Misfits like Flemmi in terms of his psychic capabilities by the time he was through. Essentially he is a SUPER SOLDIER …. trained under mysterious auspices . DARK MATTER

  9. Pls del prev post. Sorry!

  10. Matt, at least THIS fat guy knows that most, if not all, of Salisbury Beach is in the Bay State, not NH!

    You may want to spend time contemplating that one at a nice Cape spot, maybe Bass Hole. :=)