Joseph P. Kennedy was the ambitious son of a prosperous Boston saloon keeper and ward boss. He married the mayor's daughter, went to Harvard, and generally made the most of his ample connections and talent. He ran a bank (admittedly two-bit) at 25, and was number-two man at a shipyard with more than 2,000 workers during World War I. At 30 he became a stockbroker and made a fortune through insider trading and stock manipulation. He was a master of the stock pool, a then-legal stunt in which a few traders conspired to inflate a stock's price, selling out just before the bubble burst.
Kennedy may also have traded in illegal booze, although the evidence is circumstantial. His father had been in the liquor business before Prohibition, and Joe himself got into it (publicly, that is) immediately after repeal. Some believe the family business simply went underground during the dry years. He may have been strictly a nickle-and-dimer; Harvard classmates say he supplied the illicit booze for alumni events.
But there might have been more to it than that. In 1973 mob boss Frank Costello said he and Kennedy had been bootlegging partners. Other underworld figures have also claimed Joe was in pretty deep. At least one writer (Davis, 1984) thinks bootlegging enabled Joe to earn his initial financial stake, but that's hard to believe; he had plenty of chances to make money more or less legally.
The Straight Dope: What is the true source of the Kennedy family's wealth?
