The son of Irish immigrants, he was the only surviving male in the family after two outbreaks of Cholera. He started work at fourteen as a stevedore in the docks. Kennedy owned three saloons and a whisky import house, and eventually had major interests in coal and banking. He moved successfully into politics, as a sociable man able to mix comfortably with both the Irish and the Protestant elite, and he sat in the Massachusetts House of Representatives and in the Massachusetts Senate. His particular talent was for the behind-the-scenes machinations for which Boston politics became so notorious.