Roxbury Gang Murders – Henry F. Reddington

John Martorano tells a tale about Reddington. He called him a Roxbury loan shark and went on: “Wimpy Bennett borrowed $25,000 from Reddington, then figured out a way he wouldn’t have to pay. He called one of the local McLaughlins, a guy named Spike O’Toole, and told him that Reddington had been sleeping with his girlfriend. O’Toole immediately drove to Reddington’s suburban office and murdered him. The papers had another “victim” to write about, and Wimpy was off the hook for $25,000.”

Martorano’s story is the one that was believed and repeated by many of the gangsters. It is a good story to pass around among gangsters but most likely it is not true. Reddington was living on borrowed time. Lots of people were interested in murdering him.  O’Toole wanting to kill Reddington for being involved with his girlfriend, Dorothy (Dottie) Barchard, seems unlikely.  Dottie was involved with lots of guys. She was even living with OToole’s lawyer, John Fitzgerald, for a time before his automobile was blown up on January 30, 1968,  which had nothing to do with O’Toole. However, when O’Toole was on the street, as he was at the time of Reddington’s demise, Dottie usually stayed faithful.

As a side note, a similar gangster story is told by Joe Barboza. He has it that Patriarca pulled the same stunt with Sammy Lindenbaum. The Roxbury gangsters asked Patriarca to give them the okay to murder Lindenbaum. Patriarca refused. Then Patriarca managed to borrowed $75,000 from Lindenbaum. With the money in hand, Partriarca cleared the hit. He did not have to pay back the $75,000.  I suppose you could also argue Colsia got knocked off because Reddington borrowed money from him giving him a second mortgage on his home in Milton. Killing him would wipe out the debt. If we follow that theory, few gangsters would lend money to other gangsters.

On January 23, 1965, Dorothy Barchard, 26, said to be a friend of Reddington, and Edward Johnson, a Braintree real estate man, told the police they had an appointment with Reddington late on the night of the 22nd. He failed to show up. Unable to reach him by telephone, they went to his home and real estate office both located in the same building on Main Street in Weymouth. They arrived there at 3:17 a.m. to find him face down on a carpet in his office. He had been shot four times, once in the face and three times in the front of his body.

On January 27, four days later, Dorothy was held as a material witness at the request of New York authorities in the case of Joseph (Crazy Joey) Donahue. He murdered Lawrence Krebs in Central Park in April 1964. Donahue was convicted on March 4, 1965.

Crazy Joe was also under indictment in Manhattan for the murder of Presley Wilkes in a night club in February 1959. He fled the Big Apple. It was said that he used Reddington’s place as a hideout when he was on the run. He did not last too long there. The Massachusetts State Police arrested him in May as he was driving on Route 3A in Weymouth.  One theory was that Reddington tipped off the police that he was there.

O’Toole was arrested for not supporting Dottie Barchard’s two children, four days after Reddington’s murder on January 27, 1965. His hearing was postponed because Dottie had been held in custody and sent to New York as a material witness.

Reddington was said to provide, among his other activities, a hideout for “hot hoods.” Aside from Donahue, Reddington was said to have helped hide out Frankie (Machine Gun) Campbell.  According to the New York Times, Campbell died of natural causes at age 54 on October 4, 1964, while under indictment as head of an extortion gang. “His record, however, shows 16 arrests dating to 1928 on charges including armed robbery, possession of a machine gun and attempted bribery of the police. He had been convicted four times and served prison terms.”

The police believed that Reddington was into so many things that several people would have had motives to murder him. We could eliminate both Crazy Joe Donahue who was locked up at the time and Machine Gun Campbell who had died by then.

Reddington became a news story in September 1948 because of an interesting scam he developed. He sold cars that he had rented to used car dealers under the false pretenses that he was the secretary to “Father Shea” of the Jesuit Shadowbrook Seminary” who needed money in a hurry. Then, he had a banner criminal year in 1953. He was indicted by the federal prosecutors on March 13, 1953, for conspiracy to transport stolen motor vehicle in interstate commerce. In June, 1953, he was indicted for failing to register and pay the $50 stamp tax which bookies were supposed to pay. It must have been a slow time for federal prosecutors to indict for a petty stamp tax violation.

Also in June 1953, he was given a sentence of five-to six years in prison for procuring and deliver barbiturates into state prison. In August 1955, he was sentenced in federal court to seven years for conspiracy to transport stolen motor vehicles. In 1962, as I mentioned discussing Nathan Colsia above, a house Reddington owned in Milton, MA, was destroyed by an explosion. This incident clearly indicated that Reddington was on someone’s hit list. One report stated that he had been hiding out for three months.

A Boston Globe report on Reddington on January 23, 1965 noted: “Reddington was considered a close associate of George McLaughlin . . .  His name was carried on a confidential police list, identifying McLaughlin’s close underworld friends and his enemies. For a dozen years, Reddington was considered by police the boss of criminal activities, including bookmaking and money lending, in the Dorchester and Roxbury areas.”

Because Martorano is wrong or misleading on so many things, I take his story that Wimpy set him up to be hit by O’Toole because of his association with Dottie Barchard with a grain of salt. Too many other people with no connection to Barchard wanted him dead. If Wimpy wanted to knock off Reddington, he had plenty of gunfire working for him to do it. Jimmy and Steve Flemmi were as capable as O’Toole.

Add to that, O’Toole was arrested on February 24, a month after Reddington’s murder, in an apartment with fugitive George McLaughlin. George had been on the lam since May 1964. How likely is it that O’Toole would expose George by going off either alone, or with him, to murder Reddington?

It was not a Mafia hit. Reddington was known to be a friend of Raymond Patriarca. FBI intercepts showed that Patriarca was not involved in Reddington’s murder. Patriarca contacted Wimpy Bennett and Steve Flemmi trying to find out who did it. They professed ignorance. The FBI also noted that Jerry Angiulo asked Henry Tameleo, Patriarca’s liaison with Boston’s Mafia, to find out who murdered Reddington.

It is unlikely Dottie was involved with Reddington in an amorous manner. He was 25 years older. Nor, as mentioned, was she everinvolved with Ronald Dermody. She may have been always footloose and fancy free when “Spike” O’Toole was in the can but not when he was out. Gaga said O’Toole was a very jealous guy. Aside from that, O’Toole was her guy and she wanted to be with him.

A more likely suspect in Reddington’s murder is Dottie. She had a motive to murder him. I would suggest she wanted to prevent him from going to New York as a witness against Crazy Joe Donohue. We overlook women as doing hits.  We never hear the term “hitwoman.” In the movie The Sting weren’t we surprised that Loretta Solino was the hit person? It does make me wonder whether Zimmy Zimmerman, who was last seen with as women parked near the Museum of Fine Arts, was not sitting with the person hired to murder him.

Putting everything together, the most likely reason that Reddington was eliminated was due to his connection with Crazy Joe Donahue. Maybe Crazy Joe’s associates believed Reddington caused Crazy Joe’s arrest by giving information to the State Police; or maybe they did not want Reddington being summonsed to testifying in his prosecution. The New York City authorities were looking for evidence against Donahue. They had two Massachusetts women, including Barchard, held as material witnesses for being with Crazy Joe when he was hiding out at Reddington’s house. Obviously, the authorities would have wanted Reddington as a witness but his untimely demise prevented him from testifying.