James O'Toole (mobster) - The Love Triangle

The Love Triangle

Mrs. Dorothy Barchard is described by Howie Carr as being "the premier moll of the Boston underworld in the 1950s and 1960s". At the time of her relationship with O'Toole she was married to Richard Barchard, a little known charter member of the Winter Hill Gang. O'Toole fathered two children with Dorothy. Ronald Dermody started dating Dorothy after he was released from Concord Penitentary. James was a negligent father who she sued in court for back payment of child support. His wife was also allegedly involved with Joseph Barboza's criminal lawyer John E. Fitzgerald Jr. who was later maimed by a car bomb. It is said that his wife received a telephone call, in which the caller indicated that if Dorothy did not stop associating "with that guy" (O'Toole), that she and her children could be murdered. After surviving the car bomb attack in Everett, Massachusetts in 1968 by Frank Salemme he left South Boston and moved to South Dakota where he worked with the Small Business Administration and was later appointed judgeship. Frank Salemme was later convicted and sentenced to seventeen years for his involvement in the mistaken identity carbombing. Co-conspirator Stephen Flemmi was also named in the indictment but after being arrested in 1975, the charges against him were dropped.

John E. Fitzgerald advised that, in addition, his wife received a telephone call in which the caller told his wife about the relationship between he and Dorothy. Fitzgerald was asked who made this statement to him, and the caller said, "I am not going to divulge the identity of this person, but I have given the identity of this party to Jimmy O'Toole, and he will probably be in trouble when he gets out of jail." Fitzgerald also said that when he investigated to see who made the incriminating telephone calls to his wife and to Dorothy Barchard, the Patriarca crime family tried to lead him to believe that it was O'Toole's friends; that he checked with O'Toole, and this was not so.

Supposedly at some point in the 1960s or early 1970s Dermody made a deal with one of the McLaughlin brothers, George McLaughlin, that if the brothers would kill O'Toole, he (Dermody) would kill McLean. Ronald Dermody, just the week prior to his grisly slaying shot James multiple times while walking down Freeport Street in Dorchester. This attempted shooting led him to be hospitalized for more than a month. Dermody was later murdered in retribution for the failed gangland slaying in Charlestown State Prison in Charlestown, Massachusetts while serving time for armed robbery. His murderers were never caught.