Is it true that John F. Kennedy's parents were bootleggers?

Answer 1

John F. Kennedy was the son of Joseph Kennedy, the first chair of the Securities and Exchange Commission and, later, an ambassador to London. Joseph P. Kennedy was the ambitious son of a prosperous Boston saloon keeper and ward boss, that probably went underground during Prohibition. The only evidence we have that he was a bootlegger (as is often claimed) is the word of mobster Frank Costello, who said they were bootlegging partners. He was probably small time though. There is no evidence that he made his fortune this way, although he might have gotten a stake that he used for business. He was a very shrewd businessman. See Related Links below for more information on the Kennedy family wealth.

Answer 2

Quite possibly he was involved in an operation that brought liquor in from Canada during Prohibition. He was never indicted . He certainly had connections with the liquor industry and a became a distributor very soon after prohibition ended.