Whitey’s Prosecutors Quandry

A Calm August Sunset
A Calm August Sunset

I have to pause as I sometimes do in my review of Whitey’s life. I do this because a recent comment had me wondering about the influence of lawyers on this case. I was answering a comment by Norwood who suggested that the gangsters should have figured out Stevie Flemmi was an informant.

I responded that the gangsters didn’t figure this out because they aren’t usually too bright. That’s why when I was a prosecutor we were able to catch them. I like to tell the story of the time we were doing a wiretap on some bookies, The bettor started to go beyond placing a bet by entering into a discussion about some of the others in the operation. The bookie running the office replied: “be careful, the telephone may be [and then he spelled out the letters] T A P P E D” as if the cops wouldn’t figure out what he was spelling. Or in another instance, when we were listening to a couple of hoodlums talk and they began to whisper to each other thinking by lowering their voices they wouldn’t be heard.

After saying that the criminals aren’t bright, upon reflection I realized that for these criminals to get the deals they had been given they must have suddenly increased their IQs tremendously. How did they become so smart so quickly? Then I realized it was not the gangsters who became smarter. It was that they came in contact with smart criminal defense lawyers. That’s how the deals came about.

This gave me a whole new insight into this case especially when I remembered that the lawyer for the guy who got the deal of the century, John Martorano, was Francis J. DiMento of the law firm of DiMento & Sullivan. My first position as a lawyer in private practice was to work for over eight years in that firm which at that time consisted of Frank DiMento, JJ Sullivan and myself and sometimes one other lawyer.

For several years I worked closely with both men. They were as different as night and day except when it came to intellectual capacity and dauntlessness.  JJ was a cauldron on the point of boiling over; Frank was as calm as a sunny August sunset. When I messed up with JJ the rafter rang; when Frank found I’d erred he’d patiently and kindly note my errors. I had the best teachers in the art of being a lawyer.

JJ brooked no errors. He stormed into my small office with a letter that went out to a client over my signature that had a spelling error in it. He tossed it on my desk demanding an explanation. Coward that I was, I suggested the secretary made the mistake. He picked it up, looked at it and said: “I don’t see the secretary’s signature on this letter.” He turned and stomped out.

I’d spend a lot of evenings with Frank when we worked late. The firm would pick up the meal which delighted me. Frank would talk about the case he was preparing. He had this uncanny ability to assess its strength and weaknesses, to set traps that would disadvantage the prosecutors, and predict how the case would play out. He’d tell how on the second day the Government will walk into a trap he will set and how he’d spring it on the fifth day into the trial.

As fascinating were these conversations, they were also a little bit depressing. I knew I would never be able to achieve his level of brilliance or have the wherewithal to plan and assess a case like he did. Frank was far and away one of the best criminal defense trial and appellate lawyers that ever walked the streets of Boston, if not the best.

I’ll always remember what he said to me when he learned I was leaving the firm. I had told JJ my decision. JJ shrugged, not being one for any sentimentality. He told Frank. Frank came into my office and expressed his chagrin at my decision. He wished me good luck and said he was glad that at least there would be one prosecutor with a heart.

Looking at this case I saw on one side was Frank DiMento dealing for Martorano and on the other side the prosecutors.  The government made such a bad deal that they had to pretend publicly that it was something other than what it was. John Martorano wrote in his book “they knew how bad it would look, if I admitted to twenty murders, and I only had to testify against four people. So they came up with a specific target list. I had nothing to do with drawing up that list. It was a bunch of Whitey’s guys from Southie that I would have to testify against. Sure, I said. I loved that list, because I’d never known any of those guys, let alone committed any crimes with them. So I was glad to say I’d tell the government the truth about anything I did with them, which was nothing.”

I should have known that the prosecutors were no really no match for Frank. He handed them their lunch. Since that time the prosecutors have been in make-up mode. They have been thrust into the position of defending the indefensible. To do this they invented a great fiction. Much worse than Martorano, Flemmi, Weeks and Salemme is this imagined great criminal conspiracy consisting of Billy Bulger, Whitey Bulger and John Connolly. The media would add that Speaker John McCormack and Father Robert Drinan, SJ, were also a part of it.

There never was any evidence of this. Just like Martorano had no evidence against Whitey’s friends who he never met. But that hasn’t deterred the prosecutors from trying to dig out of the hole they find themselves in.


  1. Matt, my dad’s IQ is extremely high, which is a stroke of luck, just like having the physical perfection of a beautiful model. RARE strokes of luck. My dad deserves the credit for using his talents, for the work ethic, but of course, his parents had a lot to do with that as well. He also had the benefit of a first class education in a time when education was stellar. Boston Latin School, Harvard….And he loved learning, still does. It came easily to him in all aspects, especially Math (he would have been a tremendous engineer) and English, great command of the language, but he worked hard for it all. His sisters were silenced in the home when “Francis is studying!” Don’t feel bad about not being able to match his intelligence, none of his kids got his brains…I got the most attention being the eldest child, but we all got the benefit of his coaching, the benefit of the best education we could get. He is proud that all of his kids have terminal degrees and we are thankful that he paid for us to get those degrees. He always told us that if he did not need to support a family, he would have been a professor and a full time “learner”. He is close to 90 now and still working, he just loves the law, He has slowed down a lot because of my mom’s health. Thanks again for your story and kind words. I don’t know him the way his peers and colleagues do, so it is always a pleasure to hear others speak of him.

    • Millie:

      Thanks for writing. Your Dad taught me to be a lawyer but it was a hard lesson I had to learn because he was heads and shoulders above me but he was always patient with my failings. I recall him asking me to check something out which I did spending quite a few hours coming up with the answer. Having figured it out I went in to him and told him what I had conclude. I explained it to him and he said — you’re wrong (not as harshly as that) and asked me to do more research. I did and he was right, as usual.

      I used to go to dinner with him at night — he would pick up the tab — and he would tell me about a case he was then trying. He would explain what he had done and how a few day from that point the prosecutor would walk into the trap that he had just set out. Sure enough, that is what would happen.

      You suggest he was highly intelligent. That is true. But it was something that he carried with a humbleness. He did not show off his intelligence. He was always kind and considerate. I do not recall ever hearing a cross word from him (of course his partner JJ Sullivan made up for that lack). Even when I messed up a case that should have been won he never changed toward me.

      I know that he loved the law. He loved it because he understood it better than anyone else I know. It would take me many years to learn things he innately understood as a young lawyer. Perhaps, as you mentioned, it was because he had a mathematical mind that gave him that ability. Another memory is when I went in to him having encountered two identical fact situations where the judges in different jurisdictions came up with opposite conclusions. Again I spent much too much time trying to figure out why that happened. In my mind the same fact situation should equal the same conclusion. I went into his office looking for an explanation. He told me words that I often repeat today: “remember, judges make the law.” It really did not matter what the facts were what counted was what the judges decided the result should be. So much for stare decisis.

      I could go on. I look back on the days I worked with him as a happy time. He was in the front office on the left at 100 State Street, 11th Floor; JJ Sullivan was in the office at the right rear; Paul Burns in the office at the left rear; I had a small office between Burns and JJ. It was a magic time especially because the three of them got along so well and let me enjoy and learn from them.

      Thanks for writing. You gave me a chance to look back on those glory days. Say hello to your brothers for me and your dad and mother. Sorry to hear about your mother’s health. Even if your father has slowed down he is still going faster than any other lawyer.

  2. Of course I made a typo and did not double check, shame :). I meant”NEVER” underestimate, not “ever”. Hard to live up to perfection. 🙂 The other typo–should be “thank”, not “think”–see this carelessness would not be FRANK!

  3. Frank DiMento is my father. At 88 years old and still practicing, ever underestimate his brilliance or his work ethic. As your lawyer, he works night and day, with heart, soul and brain; so never underestimate the combination of intelligence and HARD WORK, which seems to have gone out of style these days. Believe me, they broke the mold when he was born. On his behalf, I think you all for the accolades. He is too modest to even know this discussion exists. Mil

  4. One of your best entries yet. Matorano would be in Otisville with Flemmi without Frank DiMento. Most intelligent man I’ve ever known.

    • Jim:
      I agree.

      • You betcha!

        • Millie:

          I agree fully with your comment. Your father taught me how to be a lawyer. The problem with that was I knew I could never reach his level since he is as you suggest quite brilliant. I’d work for hours trying to figure something out and when I came up with the answer and gave it to him he’d say “that couldn’t be right” and I’d go back to study the issue more and find out he was right. He loved the law and loved the work associated with the law. I saw him about five or ten years ago in front of Central Plaza and asked him when he was going to slow down. He smiled. I knew the answer. Not only was he brilliant he is a very kind, gentle and thoughtful person. Thanks for writing. I never can say enough about Francis X and am in his debt for his helping me out in the early days of my career.

          And, you are right, he will never know of this discussion that is why I can praise him knowing that it won’t come to his ears since I’m sure he wouldn’t like it.

  5. It didn’t take Dimento to get that deal. Pudd’nhead Wyshak had swallowed the fabrication that Bill Bulger was the ” Godfather” of the Winter Hill gang and was determined to get him. Pudd’nhead would have given Charles Manson a deal if he would implicate Connolly. The Connolly charges were the squeeze play to get Sen. Bulger. Tauro was part of the scheme that is why he gave 10 years for a letter. Connolly was expected to fold and turn on Bill Bulger. Pudd’nhead and Elwood gave great deals to all the gangsters. Dimento didn’t represent them all. He wasn’t the sine qua non of good deals. The prosecutors were giving the store away. 2. The Herald reported last week that a ” Turf War’ between the Boston Police and the State Police was unfolding at the Seaport district over who had jurisdiction. Isn’t that what took place regarding the gangster investigations? On the one side the FBI ( the largest, best funded law enforcement group) got all the credit for bringing down the Mafia and Winter Hill ( Race track case) and the lesser groups, DEA, ATF, Customs, State Police, local Police received none of the acclaim which they craved. Great resentment resulted. Pettiness ran rampant. Revenge was in the air. All the lesser groups, being unable to imprison the top gangsters, were in high dungeon over their own marginalization and the accolades the FBI got. 3. If you look at recent prosecution of Cahill, the former Treasurer you see blatant prosecutorial abuse. Cahill committed no crime, he only engaged in politics. One compared his conduct to a mayor having his name put on a plaque at a ballpark. The final result was a civil fine. A civil fine should have been the Feds demand in the Swartz case. Turner should have gotten a fine. Connolly’s letter should have resulted in a fine, not a 10 year sentence. Tauro was dishonest. He had a family member working with the State Police and had a dog in the fight on the Turf War between the FBI and the State Police. He never should have sat on the Connolly case. He was not impartial and his ridiculous sentence showed that. 4. Professor Torture invented the story of Bill Bulger’s connection to Winter Hill based on no evidence. Did the Senator have WMD in his basement? Was he giving the IRA C-4? Any stooge can make up a story. Christopher Hitchens described Torture as a ” scumbag lawyer”. Was that too harsh or could that charge be called Schmuck on Schmuck crime.

    • Neal:
      If this were a baseball game you would have struck out.
      1. Wyshack wanted the deal but he didn’t want to give away the farm. You are wrong when you underestimate DiMento. Strike one!
      2. There was no resentment that the FBI took down Angiulo. There was resentment that it undermined a state police investigation that could have done the same thing. There was no revenge nor marginalization. In the early 1980s while the Justice Department was preparing to indict Angiulo the state police and the FBI joined their forces together, as you’ll read in Tom Foley’s book, to work cooperatively. Each one felt the other contributed to their effort. They worked together since that time. Strike Two!
      3. Judge Tauro is a fine man. I know nothing about his family member working on the state police. Since there was no turf war that had no effect on anything. Even had there been this imagined turf war, Tauro is still a man of impeccable character and reputation. You suggest something that even Connolly’s counsel did not suggest that he should not have sat on the case.His sentence was at the top of the permissible sentence range, that’s true, but it was done based upon his analysis of the trial over which he presided. Tauro also sat on the John Naimovich case. You are plainly wrong in you analysis of him Strike Three!
      4. Alan Dershowitz (who advocated torturing people as long as he wasn’t one of the subjects) has a longstanding animosity toward Billy Bulger. I’m not sure where it comes from but he has no trouble asserting things about Billy that he imagines. Not only Billy he has said that Billy and Whitey were knowingly facilitated by “the Dukakises, Whites, McCormacks, Cardinal Laws, O’Sullivans, Welds, Moakleys, and Silbers . . . [along with] the cowards who appointed Billy Bulger president of UMass . . . and the reporters for 60 Minutes and The New Yorker. And he should have added any person who voted for Billy or shook his hand.

  6. Brilliant insight… Thanks for the post.

    I’ve often wondered how Martorano got that deal. Now I know that a nearly unparalleled legal mind worked in his defense. That’s about the only way a deal like that could’ve been pulled off; one-sided brilliance.

    • Kristi:
      Thanks. DiMento had a knack for smelling out weaknesses in the other side’s position.