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.