Spike O’Toole would become involved in an incident with a rival, he was involved with a woman named Dorothy “Dottie” Barchard, 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 small time member of the Winter Hill Gang. O’Toole fathered two children with Dorothy.
However Dorothy start seeing Ronald Dermody after he was released from prison. Its said that she was also allegedly involved with Joseph Barboza’s lawyer John E. Fitzgerald Jr.
In another twist to the love story John Fitzgerald was targeted in an assassination attempt by car bomb. “Cadilac” Frank Salemme was later convicted and sentenced to seventeen years for his involvement in the car bomb. Stephen Flemmi was also named as a suspect but after being arrested in 1975, the charges against him were dropped.
In the 1960s or early 70s Ronald Dermody made a deal with George McLaughlin, that if the McLaughlin brothers would kill O’Toole, he would kill Buddy McLean. However, Ronald Dermody having thought he spotted McClean walking down Freeport Street in Dorchester shot the wrong person. Wprd spread that the intended target of the failed hit was actually Buddy McClean, Dermody panicked and turned to FBI agent Paul Rico. Rico & McClean had some history also, Rico asked Dermody to meet him but also gave Buddy McClean the location. When Ronald Dermody got to the location, Buddy McClean was waiting, Ronald Dermody was shot three times in the head.
Spike O’Toole along with another associate tried to assassinate Edward Bennett, Bennett was seen as a mentor of future criminal brothers Stephen and Vincent Flemmi. at the time of the shooting, Edward Bennett had stepped out the front door of his home and O’Toole, who had been hiding in a bush shot at him from where he hid. Bennett quickly drew his revolver and returned fire and fled from the home.
O’Toole’s associate who also the getaway driver waited nearby with the car idling, panicked and drove off leaving O’Toole behind after realizing that Bennett had not been murdered, and that O’Toole and he were returning fire. Its believed the reason behind the failed hit was that George and Edward McLaughlin had surmised that Bennett had assisted in setting up the failed murder attempt of Edward McLaughlin, among other things.
Steve “The Rifleman” Flemmi’s brother Vincent was also allegedly was a target for O’Toole. Vincent “Jimmy the Bear” Flemmi left his house at around 10:30 p.m. one night to meet with Joseph “The Animal” Barboza. As he approached his car, two gunmen stepped out of the bushes start shooting, one of the gunmen shot and wounded him with a sawed-off shotgun. While recovering in the hospital from his gunshot wounds, 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 the shooters fleeing the scene, although he was not able to positively identify them. One of the alleged shooters was thought to be Spike O’Toole.
Spike O’Toole finally met his ending when John Martorano. According to Martorano’s own testimony O’Toole crouched behind a mailbox on Dorchester Avenue when Martorano said he shot through the mailbox and killed him. Martorano said “Whitey” Bulger was in another car and later complained, “I’m never going to be in a car without a gun again.”