At the age of fourteen, P. J. left school to work with his mother and three older sisters, Mary, Joanna, and Margaret, as a stevedore on the Boston Docks. In the 1880s, with money he had saved from his modest earnings, he launched a business career by buying a saloon in Haymarket Square downtown. In time, he bought a second establishment by the East Boston docks. Next, to capitalize on the social drinking of upperclass Boston, Kennedy purchased a third bar in an upscale East Boston hotel, the Maverick House. Before he was thirty, his growing prosperity allowed him to buy a whiskey-importing business. By the time he died in 1929, Kennedy held an interest in a coal company and a substantial amount ofstock in a bank, the Columbia Trust Company. His wealth afforded his family of one son and two daughters an attractive home on Jeffries Point in East Boston.