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 frien
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| - 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 frien
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| - 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.
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