Unraveling the Mystery in The Tim Flaherty Case.

Tim Flaherty 2I wrote about how Tim Flaherty was indicted for a federal crime that provided for a twenty year prison sentence and how he probably suffered through the agony of waking up each morning with the initial momentary feeling that all was well until his world came crashing down as he remembered the federal charge. His future could be imprisonment and disbarment.

Tim was a highly experienced defense lawyer. He worked first as an assistant district attorney. He had recently won a murder case on Cape Cod and a case involving some alleged gangsters in Boston’s federal court. He was not afraid to try a case. He had the skills to ensure his clients received the best defense. He was at the top of his game when the federal prosecutors struck at him. It was not that he was a stranger. They knew he had an excellent reputation.

How then I wondered in a recent post could it be that they were willing to step on him and destroy his life and then agree to have the case go away with a plea to a misdemeanor in the state court. They seem not to understand they are dealing with real lives and that their cavalier actions are quite devastating especially to people in public life or in professions not that it is any less devastating to others. It is just that if you go after a lawyer or other prominent person the mere fact of the indictment is damaging to the person’s standing in the community.

When young assistant DA’s came to work for us I would tell them we hired them because we believed they had the judgment to make whatever decision was necessary in any case they handled. They will not be second guessed or required to clear most things. However, if they have a case that will affect a person’s standing in the community then they must first clear it with me. In other words, I did not want to read in the Patriot Ledger that a complaint issued against the mayor of Quincy or a police chief or some other high official without ensuring it was a solid charge.

After I wrote about the strange case of Tim Flaherty I was contacted by John Hawkinson a freelance journalist who told me that he summarized the situation involving Tim Flaherty in some tweets on April 28. I replied to him to the effect that when it comes to Twitter I am a real dunce. He then graciously forwarded to me what he had written back then on his account @johnhawkinson.

In a group of tweets he wrote: 1/Remember Tim Flaherty, the Cambridge lawyer charged in the bizarre witness tampering case last May?; 2/ Lawyers told Judge Wolf today they’re near a deal to charge w/ Obstruction of Justice in Middlesex Superior Court and dismiss fed. Charges; 3/And Flaherty will plead guilty in state court to a misdemeanor and also lose his law license for a “period of time.”; 4/“You’re depriving me of what promised to be one of my more interesting cases these days, but there are lots of other cases”—USDJ Mark Wolf  5/“For what it’s worth, sounds like a sensible resolution rather than litigating all the intriguing issues in this case.” Wolf, said. 6/For some Flaherty background, see @BulgerOnTrial  blog https://mattofboston.com/the-flaherty-conundrum-wheres-the-crime-10680/ … and related. Note posts there are fairly opinionated. 7/Oh, and AUSA William Bloomer is going to get appointed as a (Massachusetts) Special Assistant Attorney General for the state prosecution.”

After reading the tweets of John Hawkinson the situation immediately became clear to me. Judge Wolf listened to the presentations of both sides. After doing it he noted his desire to handle it saying he was being deprived of having the chance to decide on all the “intriguing issues in the case.”

The last thing the prosecutors wanted was Judge Wolf sitting on their cases. He is bright and courageous. He was going to delve down into the depths of the case to find the truth behind the case. Who could tell where his trek for the truth would end?

I have written before how there were plenty of strange happening for him to suspect this prosecution should never have been brought for the many reasons which I previously spelled out. The prosecutors for some reason did not want go there. The settlement they worked out was equivalent to indicting a guy for an armed robbery of a bank and having the case dismissed if he pleads guilty in state court to driving to endanger during his getaway attempt.

I’ll always wonder why the case was brought? Were they unaware of the state law about accord and satisfaction. Were they unable to say no to the state cops or the FBI?

Or why it was settled like this. Did someone recognize how out of proportion the charge was to the offense? Did someone in the U.S. attorney’s office suddenly get a heart?

The bottom line is that it worked out best for all in a case that never should have reared its ugly head.  It is scary to think how close they came to destroying the life of a good man. That they backed off we can all be thankful.


  1. to the Southie Crew

    Happy Fourth

    from the never writers of the West End Peabody House
    to the ever readers of E2nd street MC irregulars

    reporting from Flying Pond Variety
    Elbows Wychulis


  2. Hello Matt,
    Great Blogs, in the Herald today an article appears about the motives of US Attorney Ortiz. In one paragraph the author mentions Ortiz’s ” Notable Convictions” of Sal DiMasi, Sen. Dianne Wilkerson, Chuck Turner and disgraced Commissioner John O’Brien. Jack O’Brien is the only one referred to as “Disgraced”. Why? I think we already know why. I hope yor prediction of reversal of his appeal is on target.
    Keep up the good work and Happy Fourth to you and yours. Will you be in the “Hoodsie Line” as usual over at Columbia Park? God Bless America!

    • JR:

      Happy Fourth. Good observation on the word disgraced. It is also used with reference to John Connolly. I read the other day that Harvey Silverglate also predicted O’Brien’s case would be reversed because of the new Supreme Court decision. Even before that decision I felt that way because it was all about patronage and nothing else. How did all the judges get their jobs?

      I’d be in the Hoodsie line if Uncle Bob was serving them and if he let us have some of that hot ice so we could put water on it and watch it bubble and smoke.

  3. Matt,

    This is unrelated to the post, but you might find this story of interest:


    Looks like Bobby DeLuca, Cadillac Frank’s one-time lieutenant, has come out of the woodwork in Florida. Turns out the rumors are true that he became an FBI informant in 2010 or 2011, was given a day in jail, and then went to the sunny shores of Florida. Now it turns out he lied to the FBI, so he’s back in the news.

    • Jon:

      Another case of the FBI using a person who was known to be involved in murders as an informant. The FBI had known since about 2004 that DeLuca was involved in that murder but would rather have had him as an informant than bring him to justice.