Joseph Kennedy was not a bootlegger during Prohibition, a claim that continues to provoke strong reactions despite the lack of supporting evidence. Historian Eric, drawing on his research, explained that Kennedy was in the liquor business before, during, and after Prohibition, but the popular image of him as a criminal bootlegger does not hold up to scrutiny. Kennedy’s approach during Prohibition was more strategic than illegal. Concerned about the social stigma attached to being an Irish liquor dealer, he purchased liquor companies overseas and deliberately rebranded himself as a British distiller.
He bought a company in England and renamed it Somerset Distillers, a name borrowed from an exclusive WASP social club in Boston that had rejected his membership. The choice of name, according to Eric, says a great deal about Kennedy’s ambitions and his sensitivity to social status. Kennedy also invested in alcohol sold for medicinal purposes during Prohibition, a legal loophole at the time. After Prohibition ended, he moved aggressively into the legitimate liquor business in the United States, partnering with figures who reinforced his desire for prestige.
One of those partners was James Roosevelt, son of President Franklin D. Roosevelt, though Roosevelt was involved in the shipping and insurance side of Kennedy’s operations rather than the liquor trade itself. Another notable investor in Kennedy’s companies was Winston Churchill. These connections, Eric notes, show how Kennedy carefully cultivated powerful and respectable allies, even as he sought to distance himself from the ethnic and commercial stereotypes of his own background.
What fascinates Eric most is not the historical record itself, but the public’s stubborn attachment to the bootlegger myth. He says that among all the claims in his books, the statement that Joe Kennedy was not a bootlegger provokes the greatest anger. Eric says he has even received threats over it, and he questions why people are so invested in believing a version of Kennedy that the evidence does not support. Eric is quick to clarify that his conclusion is not meant to paint Kennedy as a sympathetic figure.
He describes Kennedy as a rough customer, slick, smart, and in some ways diabolical. The real source of Kennedy’s fortune, he explains, was what today would be called insider trading. In Kennedy’s era, that practice was not a crime, though it was widely frowned upon. The distinction between the myth and the reality matters, according to Eric, because it changes how Kennedy’s rise is understood.
He was not a gangster running illegal alcohol, but a savvy financier who used legal loopholes, social ambition, and high-level connections to build his wealth.