James O'Toole (mobster)
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James "Spike" O'Toole (December 7, 1929 – December 1, 1973) was an Irish-American gangster from Dorchester, Massachusetts.
He was a close friend of Somerville's The Winter Hill Gang's leader James "Buddy" McLean. He was targeted for assassination by The McLaughlin Brothers gang of Charlestown, when a Cambridge gangster named Ronald Dermody fell in love with his girlfriend.
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 (Dermody) would kill McLean. Dermody's plan backfired and he wound up dead, and the McLaughlins forgot about O'Toole.
In December 1973, O'Toole (who had survived many assassination attempts) was run over by gangland assassin John Martorano while leaving a bar in South Boston.