The Strange Case of Worcester Assistant DA John O’Leary and the Massachusetts State Police: Part 1 of 2

Hard to know whether to feel sorry for forty-six year old Worcester County Assistant District Attorney John A. O’Leary who has been with that District Attorney’s office for over ten years or not. He has been suspended without pay until he clears up the mess he finds himself in. All I know about his family situation is that he has a 13-year-old daughter and owns an Audi A6. I assume losing his salary for a short period of time will not send him to the poor house. If he loses his job permanently, as some seem to hope, well that may be another story . They suggest after all he is an attorney and can continue practicing in his chosen field of law to earn a living.

That is not something easy to do after being a state prosecutor for a period of time. I had trouble.  I had been a criminal defense attorney for about 10 years before becoming a prosecutor. I handled whoever walked in the door telling me of his problems and his close friendship with Mr. Green who rarely showed up at the appointed time.  I then became a prosecutor for more than 20 years.

When I left that job I thought I could go back being a defense attorney. I found that I could no longer do it. The idea behind that job is to get your defendant client the best deal possible. It sometimes involves judge shopping – finding a judge who is more lenient in the situation your client faced. My problem was I had become an expert at deciding the punishment a defendant should suffer based on his record and crime. It rubbed me wrong to try to get him less which was my job.

Failing to get a deal I would then be obliged to try the case to help my client beat the rap even when I knew he committed the crime. I had no trouble doing it in the first phase of my career. I reasoned it was the state’s job to convict him so if I could beat the state lawyer that was how things were supposed to be. That reasoning seemed hollow to me after many years as a prosecutor. That’s just me. I don’t fault others who do it and are able to do it. But we do have to march to the beat of our own thoughts..

Whether O’Leary will lose his job or not will depend on his boss District Attorney Joseph Early. I met him once for a long discussion based on my prior experience. He seemed like a fair and smart guy interested in doing a good job. As far as I can tell has done that.

This situation though is a little different. He will face public pressure not to have a prosecutor on his staff who got arrested for operating under the influence. Can he stand up to it?

In this case I suggest he should because from what I can determine O’Leary is not in the position of prosecuting people who have been arrested for OUI. He is in the white-collar crime unit. Also, few people involved in one OUI lose their jobs.

The incident O’Leary found himself  was not out of the usual. A motorist notified the state police that a car was driving erratically west on I – 290. Trooper Gregory Zanni in his cruiser came upon the car and observed the same thing and signaled with its lights (those dreaded blue lights in the rear view mirror) for him to pull over. O’Leary pulled off the road, down a ramp and stopped in the middle of  it. Not a good sign. The trooper asked him to pull over to the side. Those observations as well as subsequent events such as O’Leary’s actions and alleged belligerence after the stop confirmed the trooper’s belief O’Leary  was driving impaired.

On that topic here’s a little hint: by not cooperating with a trooper or any other police officer you only make things worse. No matter how unfair you think the stop or request is you can only make it worse. You’d think O’Leary would have known that. Perhaps booze hindered his judgment or this may be a “do you know who I am” situation or most likely it was a panic reaction by someone in his position.

O’Leary erred in his interactions with the trooper. Like you, cops respond to respect. At a minimum by getting along  it is less likely one will have charges loaded up on him as was done here with the  endangering a child charge. O’Leary had his 13-year-old daughter with him when he was stopped.

I feel sorry he got into that jam; then again I don’t. As a prosecutor he should have known better. You don’t get behind the wheel after having more than two beers and even then it is risky. Not that two beers may impair you. It’s just that someone else might be impaired or inattentive and run into you. With alcohol on your breath you are likely to be charged. As a prosecutor when arrested your charged it becomes newsworthy.

I’ve had my days sitting around having a couple as an ADA and then driving home. Back then, unless you were in an accident, if a cop pulled you over he’d make arrangements to get you home. It never happened to me but did to others.

One day I watched the media clamor after a judge got arrested for an OUI. The cameras showed up at his arraignment and much ado was made about it. It dawned on me that as an ADA the same would happen to me. Not wanting that, I cut back substantially on having a drink before driving.

O’Leary’s case will end up with no more than a hand slap. He’ll have the embarrassment of living with his bad decision and hopefully getting his job back. That I’m writing about it shows the real danger of driving after having alcohol if you are a public official. Today there is no excuse for not calling Uber.

Where’s the strangeness? I’ll talk about that next post.





  1. Brian Merrick is correct. The stop seems ordinary but for the child in the car issue which
    might cause a longer license suspension,say ninety days, but no job loss.

  2. Matt,
    My immediate reaction was to feel sympathy for this guy..I’m guessing he has a real issue if only because he’s driving his 13 year old daughter in that state..she’s certainly old enough to know that he was drunk, which is rough on a teenager. First and foremost, he needs to deal with his problem.
    I’m not preaching, btw. Like many of us, I drank and drove after work too many times to count..often to the point of having to look outside to see if my government car was in the driveway, and chuckling when it was. That was a different time, however. I was pulled over many times and simply told to “take it slow”, or some variation thereof. Towards the end of my career, however, things changed, and changed quickly. Almost overnight, it became a fireable offense. There were occasional stories about guys getting pinched, but we always chalked that up to the guy being a dick to the PO that pulled him over. Maybe, maybe not..I think it was due to the fact that guys weren’t willing to put their own job on the line to help someone else, and rightfully so. It only took a couple of leaks to the GLOB about guys getting breaks before the breaks were no longer given. After that, I stopped…cold. Have not gotten behind the wheel after drinking ever since, and never will. I guess other than hoping he straightens himself out, my question is should he keep his job? I’m guessing that the trooper that pulled him over would be gone if the roles were reversed..maybe someone can correct me.
    Aren’t DA’s covered under the law enforcement retirement system? If so, it certainly weakens his case for keeping his job, in my opinion (if I’m right about LEO’s losing their jobs for a dui conviction). If you want to be considered law enforcement officers, you have to accept the responsibility. Thoughts?

    • Decklan,

      You make some good points. ADAs are in same group for retirement as law enforcement. They have to put in 10 years before going into it. I think he could put in his papers if he got fired.

      You are do right that times have changed with respect to driving after drinking and many other ways.

  3. John King McDonald

    Disturbing . He has a drinking problem it seems . Not the worst guy in the world . The dutiful dad is driving his daughter to a dance class . He is hammered . The cerulean lights of Trooper Zanni’s cruiser shepherd him , and more importantly his thirteen year old , to safety . Providence has intervened . He requires medical treatment for his alcohol abuse . With counseling and therapy , and a supportive DA’s Office , considering the guy wasn’t caught after a night in a strip club , but clearly is cracking under professional and familial pressures , we should be able to bring John O’Leary back into the clannish fold . We like John . Providence .

    • John,

      Nice to see you have a heart.

      • John King McDonald

        Calm down there killer . Not in the mood for your vagaries , digressions , and outright nonsensicalities , like above . If you showed more heart on John Connolly’s behalf in your … Stirring Denunciations … of injustices meted to him … he would be in better shape . I have consistently illuminated the … Nonsensicalities .. inherent in the Bulger prosecution . You twitted on for about two years that you felt he killed the two young ladies , and then , came fully around to my position . Words are cheap . Talk is cheap . Neither have done John Connolly any good . Wise up . You don’t know nuthin’ . And , that is fine with me .

  4. Time for a volunteer civilian review police board with
    subpoena powers that will set and enforce standards
    of performance for the law enforcement community

    Time for law to be taught in grades 1-12 so that you
    pass the Bar Exam when you graduate from high school

    Oh Oh!

    Grand Rapids rejects MLive FOIA appeal over police recordings

    Previously released recordings on the extension, which officers believed was unrecorded, revealed discussions between three Grand Rapids police officers attempting to help a former Kent County assistant prosecutor avoid a drunken driving charge.

    ‘Let’s pass him:’ Cops discuss ex-prosecutor’s intoxication on recorded calls

    The state Court of Appeals ordered Grand Rapids to release the recordings taken from a “non-recorded line” in response to MLive lawsuit.

    The city initially denied FOIA requests for those calls as well, but a Sept. 12 decision by the state Court of Appeals forced their release. The state Court of Appeals ruled the city must release the recordings on Sept. 12. The five calls — which revealed Lt. Matt Janiskee coached the other officers to allow former Kent County Assistant Prosecutor Josh Kuiper to get off with a lesser charge — were promptly released a day after the ruling, in their entirety and without redaction.

  5. O’Leary should be treated for his offense the same way that the private sector of society treats the infraction. That does not include loss of employment. I would never have let a valued employee go for what has been described. A man should be judged for his offense, not for the need to send society a message or the entertainment value of an Auto-Da-Fé.

    One hopes that he will learn, if he needs to learn, that there is a fundamental unfairness in stacking multiple charges on a defendant on the basis of a single incident. The abusive use of this practice is a key component in the John Connolly saga. The goal should always be a just result, not a terrified, false confession. Often there are too many thumbs on the Scale Of Justice.

    • Tadzio,

      Hope that is the case with O’Leary that he gets to keep job. The embarrassment he has suffered is surely a huge penalty.

  6. Hi Matt,
    It looks like this guy has put himself into a real jam by driving with his 13-year-old daughter in the car.

    And those flashing blue lights do tend to sober you up. You have to wonder why he gave the trooper a hard time unless he really was hammered. I’m afraid this is going to cost him his job unless there are some other factors involved here.

    • Dan:

      Hope he survives. Agree driving his daughter in the condition he was supposedly in goes heavily against his judgment. I wondered whether other adults were present or why the dance class was of such great importance.

  7. Who was in charge of the FBI when they threw Connolly and Rico to the wolves? Who masterminded that betrayal based on the stale claims of Mafia hitmen? Were Mueller, Comey, McCabe and Strozk holding high level positions? 20 years ago they got away with framing two innocents and inventing the Rogue Agent theory. The same cabal was involved in the greatest political crime in American history when the Deep State in the form of the DOJ and FBI combined with the Democratic party dirty tricks division to invent the Russian Collusion case. They spied on their political opponents using false data as the basis. They violated the Constitutional Rights of everyone in the Trump campaign in their wiretapping efforts. A coup d’tat was in the works. This was the movie Seven Days in May but with law enforcement instead of the military as the conspirators. Comey was James Matoon Scott. Fortunately the crime was exposed and the plot foiled. 2. This plot too has been exposed. The Hatch act was suppose to keep Federal employees out of Federal politics. Mueller is going to finish his job behind bars along with Comey, McCabe and others. Once he decided to charge Flynn he joined the criminal conspiracy using illegally leaked signals intelligence. Had he indicted the leaker instead he would have absolved himself yet he chose to join the other wrongdoers. The same gang that framed Connolly and Rico is still functioning in D C but not for long. Drain the swamp.

    • NC:

      Connolly was indicted in December 1999. Louis Freeh was director of the FBI. They ones you mention had nothing to do with his indictment. Comey at that time worked in the private sector. Mueller was US attorney in California. McCabe had been in the FBI 3 years and so had Strozk. None held high level positions. I suppose there was a prior Dark State prior to the one that exists now or are they part of that dark state.

      You do remember that the FBI under Comeey was the most responsible party for Hillary’s loss. If Comey was working for the Dark State would he have announced the reopening of an investigation. Had there been a coup d’tat who stopped it?

      2, How could Mueller join the criminal conspiracy if he was already a member of the Dark State. You are getting your Dark States confused. I suggest you wait for Flynn to tell his story.

  8. The world has changed since I was a young ADA. Cops don’t give ADA’s (or judges) a ride home anymore). Some wouldn’t even help another cop. The problem is that when one should take an Uber home, one doesn’t have the judgment to do it. I saw a story about arguments that Congress should pressure the states to lower the “legal” limit of alcohol permitted from .08 to .05. When I started out, if people blew a .05, they were released and permitted to drive away.

    O’Leary should do a quick admission and get his CWOF and 24D program out of the way. If the world hasn’t changed even more than I think, he should then go back to work. Early seems like a stand up enough guy to permit that.