James "Spike" O'Toole (December 7, 1929 – December 1, 1973) was an Irish-American criminal from Dorchester, Massachusetts. Biography James "Jimmy" O'Toole was born to first generation Irish 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 (the Charlestown Mob) of Charlestown, when a Cambridge Winter 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 still married to Richard Barchard, a little-known charter member of the Winter Hill Gang. Barchard was locked up at Alcatraz for his part in robbing a bank in Hammond, Indiana, with Whitey Bulger in November 1955. O'Toole and Dorothy lived together from January 1960 to February 1965. During that time, he fathered two daughters with Dorothy. In January 1965, Dorothy brought a suit against O'Toole for non-support of their two toddler daughters. It was not her own idea. She had applied for aid from the State, but officials had insisted that she name the father of her children. Otherwise, they said, she would not be eligible for assistance. Spike was arraigned on a morals charge for having two children out of wedlock with Dorothy. Dorothy Barchard was also involved with Joseph Barboza and criminal lawyer John E. Fitzgerald Jr. during this same period. Fitzgerald was later maimed by a car bomb while driving Barboza's car. Fitzgerald later told the FBI 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. John E. Fitzgerald