Wrongly Attributed to the First Irish Gang War- Ronald Dermody (Part 2)

On September 4, 1964, at 11:00 p.m., Dermody was in the driver’s seat of the car he had borrowed which was stopped at School and Belmont Streets in Watertown. The window on the passenger side was rolled part way down. He was shot at four time; three slugs hit his body. The fatal shot hit him in the neck and passed out the left side of his head. Newspapers reported the shots were fired through the partially opened window. I suggest that is wrong.

Whoever shot Dermody was sitting in the car with him. That would account for the bullet going into his neck and coming out the left side of the head – an upward trajectory that could not likely be fired from outside the car. Aside from that, the medical examiner report noted “powder burns on the victim’s neck which indicated at least one bullet was fired at close range.” He was first observed slumped across the front seat with his head lying on the passenger side, indicating he was sitting in the driver’s seat when shot.

The night before Dermody’s murder, Charles Robinson, 33, was walking along Broadway in Somerville, toward his home when a man came up and shot him with a .22 caliber gun. He was wounded in the left hip.  After being shot, he said he walked a mile to the Central Hospital. He was later transferred to Massachusetts General Hospital. He could not explain to the police why it had happened. He had never seen the man before.

After speaking with Robinson, for whatever reason, the Somerville police sent out a teletype that night seeking Dermody for questioning. Where did it get information to connect him to the shooting? Robinson did not know Dermody. There were no witnesses to the nighttime shooting because no one came to Robinson’s aid. The car Dermody was killed in, which I assume was the car he would have used going over to Somerville, was registered to a woman in Burlington.

I first sought to determine how the police decided Dermody was the shooter? They sent out a teletype as I mentioned. Was a tip received they deemed reliable from some source? Who could that have been if there were no witnesses to the shooting? All I can figure is they showed Robinson a photo array and he identified Dermody.

This puzzled other people who said it must have been because the Somerville hoodlums recognized Dermody as he fled. How would they know he was fleeing anything? Also, since when do criminals go out of their way to help the police by tipping them off. Further, Dermody was not a Somerville guy so few would know him.  He had spent the prior eight years in federal prison. He was back on the street for only four months. Gaga Murray told that he had been in contact at times with Buddy McLean the Somerville leader so if true he did have some connection there, but it could not have been widespread.

But assuming some knew him and saw him driving. How did they connect him to Robinson’s shooting? Why would they want to call the cops? Logically Robinson had to identify him through a photo array.

Here are the known facts: Robinson was shot on September 3; Jimmy Flemmi was shot at by the McLaughlins in Dorchester on September 3; Dermody was murdered on September 4; Dermody may have been dating Dottie Barchard although he may have been dating her sister; Dottie was the girlfriend of Spike O’Toole; O’Toole was a McLaughlin associate; he was serving time along with Gaga in the Dedham House of Corrections; and the Somerville police believed Dermody shot Robinson.

The answer to who it was that murdered Dermody must fit into these facts. There is always a gangster explanation for things like Dermody’s murder. It will usually be based on rumor, put out for public consumption to spin a good tale, or to have the police run down the wrong trail. The media people usually go along with the gangsters’ explanations. Most media members are too busy to pry deeply especially if it has been accepted by other media folk.

The gangster and media story is:

  • Dermody is in love with Dottie. Spike O’Toole, the father of Dottie’s two children, had become his rival. O’Toole was a hardened criminal. Dermody figured with O’Toole in the picture, he had no chance with her. O’Toole was very jealous of Dottie. Dermody went to the McLaughlins. He offered to murder their great enemy, Buddy McLean, if they would murder O’Toole. With O’Toole dead, he had a clear shot at Dottie.
  • The McLaughlins agreed to Dermody’s deal. Dermody headed over to Somerville looking for Buddy McLean. He saw a guy walking down Broadway that resembles McLean. Dermody shot the guy and fled. The next day he learned the Somerville police are looking for him. He found out about this because his estranged wife called him to tell him the police raided her house looking for him and saying he shot a guy in Somerville the night before.
  • Dermody then panicked. He called FBI agent Paul Rico. They arranged to meet. Rico then called Buddy McLean and told Buddy about the planned meeting place. Buddy went there and killed Dermody. Buddy then hid out in the basement of Agent Rico’s house where he lived with his wife and five kids for a week.
Dorothy Barchard and Lawyer

The whole story falls apart if Gaga is correct and Dermody’s girlfriend is Dottie’s sister. It is hard to disbelieve Gaga since he was close to O’Toole and Dottie who lived with them for a while. If Dermody is dating Dottie’s sister, he does not go to the McLaughlins to have them kill O’Toole to give him a shot at Dottie. Nor does he go to Somerville and shoot Robinson.

Assume that the Dermody is dating Dottie rather than her sister, the biggest flaw the gangster/media story is how would anyone relate the shooting of Robinson to an attempt to shoot Buddy McLean. If the McLaughlin’s had made that deal they were not about to tell Buddy about it. Further, there is no showing the McLaughlins wanted Buddy dead at that time. If they did, they would have acted against him as they would later do after Edward “Punchy” McLaughlin was murdered.

At the time we are talking about the McLaughlins had another enemy they were involved in fighting. The same day Robinson was shot, they were shooting at Jimmy Flemmi who they believe murdered Harold Hannon. Being involved in trying to murder Jimmy Flemmi, Buddy would have been far from their minds.

There are other big holes in the gangster/media story. McLean and O’Toole were both dangerous dudes. If Dermody wanted O’Toole murdered, why not do it himself when O’Toole got out of jail? O’Toole was only doing a short bit nor was he as tough as Buddy McLean, It would have been more straight forward rather than involving himself in the machinations with the McLaughlins.

Further it would make no sense for the the McLaughlins to ally themselves with a recent parolee with whom they had no prior relationship. The last thing they would do was trust a stranger who could later implicate them in the murder if he were caught and interested in making a deal for himself to their detriment. Aside from that, they would never agree, or even pretend to agree, to murder O’Toole. He was a close friend and valued member of their group. The idea that they would agree is preposterous.

Here’s another hole. A gangster like Dermody is not going to hit someone with a .22 caliber pistol. That is not considered a murder weapon. Dermody would know that Buddy was a guy who usually carried. He would know a .22 would be no match for a .38.

Add to that, if his intent is to murder Buddy, he would not shoot him once in the hip and then take off. Robinson’s story is more akin to a lover’s dispute where one normally non-violent guy or gal is trying to scare off another by using a light weapon and not planning to fatally shoot him. The way in which Robinson was shot clearly indicates it was not a gangster hit.



  1. William F Fitzgerald

    There is a small photo on the top left of the article that looks to be four gents at Castle Island. Can someone advise who they are or provide a caption for it? Is it Matt?

    • It’s Matt and some guys from the neighborhood. I will try to get a caption with a bigger photo.

      • William F Fitzgerald

        Thanks so much. I had guessed it was but Matt always told me not to guess! Regards from the Fitzgeralds to all Connollys

  2. Thanks for a great article and I am glad that you are continuing this series.

  3. Can Matt’s research be edited into a book? Has anybody tried?

    • We hope to. He had the Boston Gangs and Why Whitey mostly complete. We will roll them out here first for comment and enjoyment of his blog readers.