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I believe he ran for mayor of Boston in 1959. However, I don't think he ever got elected. ACTUALLY, George O'Brien did not run for mayor of Boston. In fact, he was the business manager of Bostons MTA Carmen's union which represented streetcar and trackless trolley operators. He served as business manager of Local 7 and later as its legal counsel.

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Q: Who in Boston MA politics is George O'Brien?
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