James "Jimmy" O'Toole was born to first generationIrish immigrants from County Cork, Ireland. He was a close friend of the leader of the Winter Hill Gang of Somerville, Massachusetts, James "Buddy" McLean. He was targeted for assassination by the McLaughlin Brothers gang of Charlestown, when a CambridgeWinter Hill Gang founding member and bank robber named Ronald P. Dermody fell in love with his twenty-nine-year-old German-English girlfriend-mistress Dorothy Barchard. Dorothy was also the stepmother of Joseph Dermody, the son of Joseph from a previous marriage. James was also referred to as "Red" because of his thick head of red hair that he fashioned with Brylcreem into a ducktail. Although James was his baptismal name he was called "Spike" by his friends. He was a close friend of Charlestown Mob member Francis X. Murray, Harold Hannon and Wilfred J. Delaney who would later be murdered by rival gang members.
The love triangle
Mrs. Dorothy "Dottie" 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 Penitentiary. 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", 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 him 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 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.
James and another associate, allegedly Francis X. Murray, tried to shoot Edward Bennett, the criminal mentor of future criminal brothers Stephen Flemmi and Vincent Flemmi. Edward had stepped out the front door of his home and O'Toole shot at him from where he hid in the bushes nearby. Edward quickly drew his revolver and returned fire and fled from the home. O'Toole's accomplice and getaway driver thought to be Murray who waited nearby with the car idling across the street panicked and deserted his friend after realizing that Bennett had not been murdered, and that O'Toole and he were returning fire. Afterward the reasoning behind the failed ambush was that George and Edward McLaughlin had surmised that Bennett had caused among other problems with their criminal activities, assisted in setting up the failed murder attempt of Edward McLaughlin.
On the evening of May 10, 1965 Vincent Flemmi left his home at 10:30 p.m. to meet with his friend and criminal associate, Joseph Barboza. As he approached his Oldsmobile Cutlass, two gunmen stepped out of the bushes shooting at him, one of the gunmen shot and wounded him with a twelve-gauge sawed-off shotgun. While recovering in the hospital from his near fatal gunshot wound, Flemmi informed his FBI handler H. Paul Rico that when he was shot, the momentum of the gun blast spun him around and that he saw his bungled killers fleeing the scene, although he was not able to positively identify them. The alleged shooter was thought to be O'Toole.
Falling out with the Mob
He had been receiving death threats since 1963. In December 1964 Spike and Francis X. Murray received telegrams the day before they were set to be released saying, "You will receive the same benefits of Harold." The anonymous telegram sender was referring to mob associate Harold Hannon, a 54-year-old criminal associate whose bound body was found floating in the Boston Harbor the previous August along with Wilfred J. Delaney. In September 1964 after Spike and Francis were released, there was an attempted shooting of Murray as he drove along the Southeast Expressway in South Boston. The shooter was never identified and his intended death sentence was never carried out unlike his friend O'Toole. James would later be arrested for another crime and served time in Massachusetts Correctional Institution - Cedar Junction as an accessory after the fact in the murder of Dorchester bank clerk, William Sheridan. Sheridan was shot to death by George McLaughlin while in the middle of an armed robbery. In December 1973, O'Toole was run over and killed by gangland assassin John Martorano while leaving Edward G. Connors' saloon in Savin Hill, Dorchester.
Potential confrontation with Rockball O'Rourke
O'Toole and 46-year-old Joseph M. O'Rourke from Medford, Massachusetts were arraigned on charges in 1970 and imprisoned at the same jail while awaiting trial. O'Rourke, a powerful and loyal associate of the Charlestown Mob, was being held for his involvement in the shooting of Boston patrolman Robert Noonan. Detective John P. Flaherty of the Fields Corner Division stated that Officer Noonan's family was afraid of potential uprising from members of the Charlestown Mob and that a police detail he placed around his bed at Boston City Hospital while he recuperated from his gunshot wound. O'Rourke allegedly shot Noonan after he tried to break up a bar brawl. O'Toole was remanded to the Charles Street Jail and prison authorities later had O'Rourke sent to the Billerica House by Judge Reuben L. Lurie on advice from the Assistant District Attorney John Mahoney. He and prison officials were worried of a possible outbreak of violence in the streets of Boston and in the prison itself among its incarcerated Charlestown Mob and Winter Hill Gang associates. The city had just overcome a brutal violent gang war and did not want another one.
Repercussion of his murder
After O'Toole was murdered, former associate Mullen Gang member Paul McGonagle was sentenced to death by James J. Bulger. Bulger took part in McGonagle's murder with the help of Thomas King and buried him on Tenean Beach in Dorchester, Boston. Bulger drove McGongale's car off a pier in Charlestown, Massachusetts and tossed his wallet into the water. This was to give the impression of what had happened but no definite solid answers. McGonagle's friends were also persuaded that Paul had been murdered by rival mob associates in Charlestown and take a misguided revenge against the McLaughlin Brothers gang, therefore eliminating more of the Winter Hill Gang's rivals.
