§35 Whitey Joins Flemmi And Connolly: Breaking The News [Re-Examining Whitey Bulger: The Learning Years]

An Early Morning Beckoning Spring's Arrival
An Early Morning Beckoning Spring’s Arrival

Whether Whitey was an informant as all the world believes or whether he was not as he and his attorneys suggest really changes little. It gives Whitey the feeling that he never faulted on his loyalty to his fellow criminals nor has he joined the ranks of that much despised group of Irishmen who have betrayed one cause or another to save themselves.

The most dastardly aspect of Whitey’s claim is his undermining of his friend FBI Agent John Connolly who loyally served him all these years. His allegation that he paid Connolly for information might in his mind redeem himself in the eyes of his fellow hoodlums. Nevertheless, he is betraying Connolly who has maintained he never received any money from Whitey. Whitey by attempting to shed the label informant actually cloaks himself in it. He is informing on Connolly, his protector.

I suppose one can accept that Whitey may truly believe he was not an informant; on the other hand, one must also accept that he knew Stevie Flemmi was an informant. He was either a conduit for Stevie’s information to Connolly or present when he imparted it to him. It was, at least from Connolly’s viewpoint, a tacit acceptance by Whitey of the role of informant.

The discussion over his status is more theoretical than practical. It’s not what he did that really makes difference but the consequences of the perception. The FBI listed him as one, even though he might not have not known that or agreed to become one; the FBI treated him as one; even though he suggests it was because of money not information; and, after learning Stevie Flemmi was an informant and continuing his partnership with him and involving himself in the dynamic trio, he became an equal beneficiary of Flemmi’s deals: the FBI’s averting its eyes to his activities and its protection of him.

When Whitey first heard from Stevie after innumerable conversations that he was working with the FBI Whitey must have been indifferent to it. Stevie was now his bosom buddy. Whitey had no friends in the Mafia so he would not care if Stevie informed on its members. Or better put, he had an actual disdain of the Mafia. Kevin Weeks testified at Connolly’s trial as I noted in my book Don’t Embarrass The Family Whitey did not like Stevie’s association with Salemme, who was to become the leader of the New England Mafia family. He complained that Stevie was becoming a liaison to the Mafia.

Neither would Whitey care that much about his associates in the Winter Hill leadership. He’d gone to Winter Hill for protection from his Southie rivals. He didn’t need that group anymore. He had Stevie Flemmi who had a fearsome reputation in the underworld at his side. Together they had begun to eliminate the dangers to him posed by his Southie enemies.

Whitey was an open book in one sense. He was interested only in what was best for Whitey. He’d have probably already figured it out Stevie was an FBI informant before he was told. The dismissal of three serious felonies against Stevie after coming back from a five-year flight must have caused some eyebrows to be raised. These guys survive by knowing what is happening around them.

He probably shrugged at the revelation. He had wedded Stevie for better or worse. It was of paramount importance that their marriage be preserved.

Whitey’s response to Stevie’s revelation most likely was that he had no problem with Stevie being an informant as long as two things never happened: Stevie would not jam him up and he would never become an informant himself.

Once over that hurdle Stevie could tell Condon and his new handler Connolly that Whitey was on board. Connolly would eventually come to feel more comfortable with Whitey. That suited Stevie who wasn’t overly fond of Connolly. He was happy to work through Whitey.

It’s difficult to know exactly how or when Stevie told Whitey of his FBI arrangement. Stevie. as is his wont, lied about how it happened. Whitey has yet to tell and with his new spin on things who knows what he’ll come out with. Connolly has already told an internally inconsistent tale.

What I suggest happened seems to fit. Two wily gangsters sitting down and planning their future mindful of their similar habits, desires and goals. Both had to be on board the FBI relationship as subsequent events such as the dinners confirmed.

Flemmi came back from his flight in May 1974. When Connolly opened Whitey on the FBI books on September 18, 1975 Whitey and Stevie had already eliminated one of the Southie guys who had a hand in Whitey’s pocket and presented a threat to him, Paulie McGonagle, a Mullen gang boss. Whitey would claim it was self-defense. He was defending the love of his life, money.


14 thoughts on Ҥ35 Whitey Joins Flemmi And Connolly: Breaking The News [Re-Examining Whitey Bulger: The Learning Years]

  1. The fact gangsters said Connolly took money is meaningless. If the gangsters said they paid four cops from Savin Hill ( Lewis, Flynn, Bradley and Mullane) all whom you know to be honest or they paid four Quincy cops you know are honest you would laugh at their claim. The claim against Connolly is just as ludicrous.

    1. Neal:
      Gangsters say what they believe to be necessary at that moment for them to gain an advantage. I believe Yakka McFadden would tell people he loved them, and put a kiss on their cheek, and then with a roundhouse right he’d slug them right on the spot where he left his kiss. I suggest we can thank Yakka for giving the Ammerican military the idea of putting the laser on a target and then having a smart bomb follow the point of the laser beam.

  2. Matt, I wrote “beyond a reasonable doubt” that’s the standard for prosecution; the standard for arrest is just probable cause, sufficient evidence, something like that. Anyway, we all know this is very tough terrain to slug and slosh our way through. At least we agree that career criminals, sociopaths and psychopaths are tough pieces of rope and their tall tales are tough to swallow.
    Have a good day!

    1. Bill:
      You are right – it is only probable cause to arrest. A prosecutor before indicting a person should have no reasonable doubt the person committed the crime.

  3. Matt, Tuck would look me straight in the eye without blinking and deny stealing the watch I just saw him palm and put in his pocket. A few more notes from the underground: This’ll be relatively brief: (1) John showed no consciousness of guilt when he told his secretary what to do with his check: Throw it in the top drawer with the other checks. The drawers were left open. He wasn’t trying to hide anything.. . . 2. John did show guilt in dealing with Weeks while trying to help Flemmi, the same guilt, caution and sensitivity I showed in dealing with career criminals. . . . John Connolly tried to help Flemmi; the letter was inexcusable, but an exercise in free speech, no matter how false, defamatory or mean-spirited; writing a letter to a judge is a free speech and constitutionally protected exercise of the right to petition the government for a redress of grievances; if he stood outside the courtroom with same words plastered on a placard, everyone would understand the free-speech implications; the falsely accused cops, of course, could have sued him civilly for slander/libel. I understand how the judge, prosecutors and cops, who were furious at the letter, could conceptually it as “obstruction of justice.” Criminal or not, the letter was wrong and way beyond the pale. 3. Remember that even Colonel Foley’s vaunted State/Federal Strike Force indicted Bulger and Flemmi for racketeering; not for murder. No one knew Flemmi was a vicious serial killer until about 1999, 2000. If anyone in law enforcement knew it (beyond a reasonable doubt) they would have arrested him; in fact they were duty bound to arrest him; no one in the press until about 2000 reported that Flemmi was a vicious serial killer; When Grieg fled with Bulger in 1995, Bulger had not been indicted or formally accused by anyone of murder. Morris in 1999 said he “suspected” Flemmi/Bulger killed Brian Halloran in 1984. . . . Peace!

    1. Bill:
      Yesterday I went back through the comments looking for a prior post. It took me an inordinate amount of time. I find I’ve let too many posts by too many people go through unedited. As a result a lot of posts are repeating what was previously stated. This makes people interested in finding out about prior comments frustrated in having to slog through some of the long posts that have been made by many people repeating things they have already said. I realized that to make the comments relative and have people read them I have to start editing them to leave in the main points and leave out what has been repeated before. I’ve done this before, in fact, I deleted one comment entirely, and only one, which was filed by a person who put me in a position where my response to him would have bordered on being cruel.
      Now I feel I have to make comments more concise. I edited your post and indicated where with “. . . ” I think we’ve had enough speculation on John Connolly and the way he could have obtained money. Some of the other items I though went beyond the subject matter that I want to concentrate on although they were informative. I hope you don’t mind but I do feel a need to make the comment section more accessible because it contains a lot of good information beyond my post.

  4. Matt, Neal, we have and will continue to debate these issues ad infinitum. One point, though: Not one of us have seen the transcripts and none of us knows what Whitey will testify to, or even if he will testify. My only counter punches — ones I’ve thrown before— are these: Flemmi was in jail for eight years before he accused Connolly and Rico of being bad cops; Weeks said ludicrous stuff like Whitey had six FBI agents with machine guns ready and willing to do Whitey’s bidding; Flemmi and Salemme are proven perjurers; the Boston jury rejected most of the serial killers’ and Morris’s testimony. And, Whitey says he was never an informant. Lot of reasonable doubts all around about all of their statements. So, you do make strong points! We’ve made counterpoints. You’ve made counter-counter points. Keep on punching!

    1. Bill:
      We can’t reject everything the felons say. For instance, when they are asked to state their names I suggest that they may be telling the truth. As to all else, one must be wary.

  5. Very good posts. The evidence that Connolly took money from the gangsters is non credible. Remember in the 80s taxes were low thanks to Reagan (25% income tax cut and reduction of the top rate to 28%)and Gov. King who implemented prop 2 1/2. Connolly took home about 50G a year at that time which would translate to about 130G take home today. Imagine a single state cop living in a two family, driving a government car taking home over 10G a month. He would have more money than he could spend. He could have a much more lavish lifestyle than Connolly. Having quality clothes would be easy. 2. A few decades past a judge in Roxbury Court ( Elwood McKinney) ruled that Cocaine was harmless and thus legal in his jurisdiction. Isn’t that in effect what U. S. Att. Elwood Stern did when he dealt with Salemme. Stern concluded Heroin was harmless and never inquired of the NE crime boss?

    1. Neal:
      The only gangsters who could have given Connolly money are Whitey, Weeks and Flemmi. They all say they gave him money as far as I am led to believe. He also didn’t cash his pay checks. There can always be other explanations for a person having money. He could have borrowed it from rich friends or found some in a hidden corner inside a cell in Fort William or won it playing poker at L Street bath house. I’m just saying that Whitey said he paid for the information he received and Connolly was the one giving him the information. If he paid for it, I assume he paid Connolly and not the nuns at St. Agatha’s.

  6. Matt, as you know I don’t trust federal prosecutors, Wyshak et al. I await with bated breath to hear what James Bulger says on the witness stand. I discount “bluster” on intercepted phone calls. I know the prosecutors have said they recorded Bulger saying he paid off Connolly. I’ll go out on a limb and bet a dollar to a dime that what Whitey said on his telephone calls is that he paid everyone off. He thinks if he gives a guy a bottle of wine he’s paid them off. I know Weeks has testified about Connolly’s nickname being on envelopes stuffed with cash, and Flemmi has testified in Miami that Connolly took exactly $235,000 over 15 years. (Flemmi kept accounting records? Why not $250,000? Whatever happened to that cash? Evaporated? It’s still in a closet in a shoe box beside the Gardner heist’s artwork on Silver Street in Southie?) I don’t believe a word that comes out of the mouths of the serial killers, nor from Howie Carr, nor from the Boston Globe’s devious “reporters”; proven liars all. Maybe, Whitey thinks that what he was giving to the admittedly corrupt Morris was being split with John Connolly. Who knows? All I can say is that I heard with my own ears John Connolly state clearly and unequivocally in a Miami courtroom in Nov./Dec. 2008, “I never took a dime.” I believe him. His answer, at the post-trial sentencing hearing, was in response to a direct question from Fred Wyshak, “Did you take money from them (the gangsters).”
    2. Have you seen the transcripts of the Feds’ intercepted telephone calls?
    3. Also,please elaborate on Connolly’s statements about recruiting Whitey being “internally inconsistent.”
    4. Thanks for all your good work and for your hard work in keeping this blog going. I have been educated, edified and enlightened by reading your columns and your readers’ comments. I still say John Connolly was framed, both in Boston and most egregiously in Miami. I’ve mentioned before that in working-out at the L-Street Gym (the Curley Recreation Center) for 20 years, my friends and I have had bloody battles over all of these issues for 20 years, day in, day out.

    1. Bill:
      It is beyond bluster. Both Whitey and his counsel have said he paid for information. Whitey will not testify if the immunity defense is ruled inadmissible. You don’t want to accept what the prosecutors have alleged because you do ont want to believe it. If it were not true I’m sure Carney would have corrected the record. He has been provided with a copy of the telephone calls. The calls were not “intercepted” in the investigative sense, they were done at the knowledge of the person speaking on the telephone.
      In putting things together if Whitey suggests he was getting the FBI protection, then there must have been a reason for this. It was either information or money that he was providing. He said it wasn’t information so what was it. Remember it was Connolly who Whitey dealt with. The suggestion that Whity was giving money to Morris who was splitting it with Connolly does not fit. You are imagining too man scenes to avoid dealing with Whitey’s assertion he gave Connolly money for information which seems to be on the record.
      What do you expect Connolly to say? Do you think he’d admit to taking money from Whitey? We’ve been through this before. If Whitey says he paid Connolly money it will be hard to suggest he didn’t — as Weeks and Flemmi have already testified that he did.
      2. Whitey’s lawyers have seen the transcripts. They have not said anything to contradict the prosecutors and I assume they would have if that was the case.
      3. I was referring to Connolly’s suggestion that he recruited Whitey to inform against the Mafia when Whitey obviously had no information to give on the Mafia. That may not have been internally inconsistent when I rethink it. Rather it was something that makes no sense. An internal inconsistency of Connolly’s would be that he has said the FBI put him in the business of dealing with murderers and also said he did not know his informants were murderers.
      4. John Connolly was not framed in Boston. His counsel did not dispute some of the convictions. He wrote the letter to Judge Wolf attempting to discredit good police officers he did not like in an attempt to help Flemmi; he lied about being in contact with Flemmi’s defense team. I keep in mind Connolly was free to associate with anyone after he left the FBI. I don’t understand him choosing to associate with Flemmi and Weeks. The impropriety of his association was shown by his use of code names between himself and Weeks and the circuitous way they had of contacting each other. Flemmi is one of the worst people who ever walked the streets of Boston. Weeks is a strong arm thug. Connolly went out of his way to try to abort the prosecution against Flemmi and met time after time with Weeks to help him. How do you explain him doing that?

    2. I thought Whitey said upon arrest that John Connolly was innocent? I submit that even if he did say Connolly took money, it was into a microphone at the PHOC and the context must be examined.
      Whitey is locked down for at least 23 hours a day, arguably locked down tighter than any other prisoner in the US. His brain is permanently haunted by the the CIA’s MK Ultra experiment. When he is eventually let out of his tiny isolation chamber, he is led directly to a microphone connecting him to some visitor from the world outside, and Wyshak. But it may be his only chance to speak with another human for days, or perhaps ever. He’s over 80 years old. He’s been in the tiny torture chamber for days. (Whether his speech into Wyshak’s microphone is a product of free will, or it is a product of government-inflicted duress is a different question. Based on Judge Stearns’s “disgraceful” behavior, suppression was not an option.) The one thing Whitey can control under these circumstances is MISINFORMATION…
      Furthermore, Whitey’s recorded words are then filtered and arranged by Wyshak and he releases what he wants to the world, with or without proper context. Be assured Wyshak will arrange things to promote his theory that Bulger and Connolly are the only bad actors and there’s no need to investigate other federal law enforcement officers or gangsters. That’s how it comes to us and we are left to speculate.

      Is Whitey is babbling nonsense into Wyshak’s microphone, or is he still strategically savy enough to use the only instrument of control left in his world to influence what he can?
      Is he exposing too much, or is he leading Wyshak into traps on cross examination?

      1. Patty:
        You bring up some good points. you point out how Whitey is locked up for 23 hours most days and all he has to speak to is the bored prison guard who stares at him in his cell. That will have an effect on an 83 years old guy whether he was or was not a CIA guinea pig. Every communication he has with the outside world, except perhaps with is lawyers, is read by the prosecution. He has forfeited his right to privacy and is doomed to spend the few remaining months or years similarly situated. I don’t know what his state of mind is although I’m told his physical condition has weakened. All I know is that Wyshak has given Carney recordings upon which Whitey says Connolly was paid by him. Like with all gangsters it is difficult to tell when they are speaking the truth because they don’t speak to do other than to benefit themselves and if they think the the truth may hurt it is replaced with a lie.

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