James O'Toole (mobster)

James S. (Spike) O'Toole (December 7, 1929 – December 1, 1973) was an Irish-American Charlestown Mob associate and criminal from Dorchester, Massachusetts.

James "Jimmy" O'Tuathal (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.

Mrs. Dorothy "Dottie" Barchard is described by Howie Carr as being "the premier moll of the Boston underworld in the 1950s and 1960s". both 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" (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.

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