The Kennedys have often been referred to over the years as American Royalty, their kingdom square in one of the oldest European Colonized regions in the United States. The Kennedys first arrived in 1849, and produced their first politician in Patrick, who served several terms in the Massachusetts House and Senate. Patrick was the Patriarch of arguably one of the most Cultured families in the country, and would be the grandfather to arguably one of the most popular presidents in American history, John F. Kennedy, whose love for the Daiquiri has already been documented in ‘Spirits of the Oval Office,’ back in early August.

Middle; Joseph Kennedy, Right; John F. Kennedy

Even though JFK is the most famous of Patrick’s descendants, it is actually his firstborn child, Joseph, who might have the more interesting connection with alcohol. Joseph Patrick Kennedy was for all intents and purposes, the primary creator of the family fortune, utilizing business practices that would later become illegal, such as the stock-pool, in which groups of investors would work to inflate the value of a stock and then dump it before it crashed. He was also involved in real estate, merchandising, commodities, and import/export. It was these industries that he used to build the Kennedy fortune, but over the past several decades, many rumors have circulated that there was a slightly more illegal practice that he had engaged in during the 1920′s: Bootlegging.

Shortly before his death in 1973, the Prime Minister of the Underworld, Frank Costello,  said that Joseph had been one of his business partners in the bootlegging business. This claim is widely disputed, and there is no proof that it actually was the case, however when looking at the timing and opportunistic nature that characterized Joseph, it is not hard to imagine.

During the 1920′s, Joseph became close friends with Franklin D. Roosevelt, whose love for the Martini has also been chronicled in ‘Spirits of the Oval Office,’ and as we know, FDR repealed Prohibition in 1933. Prior to this, Joseph Kennedy had already acquired import rights for Scotch Whiskey as well as a variety of spirits from a firm in Canada. In addition to that, his import/export company was the exclusive American agent for Gordon’s Gin and Dewar’s Scotch. Perhaps it was just his impeccable timing that caused people to mutter about him being involved in bootlegging, but there were several annecdotes out of the 1920′s, that Joseph had supplied bootlegged liquor to Harvard Alumni parties. While that is not exactly crippling evidence, the testimony of Frank Costello bears far more weight. Through his life, Costello was fond of recalling the political and social figures that he had held association with during his time as the Boss of the Luciano (later Genovese) Crime Family, and it was said that a judge was not appointed in New York City without Costello’s approval. One of the early rackets that Costello was engaged in was the the ‘Big Seven Group’ which controlled rum-running and liquor importation around the country.

Costello was a widely respected man and was well known to be in close social circles with influential Democratic Party members, and this connection was used to bribe officials through every position in order to make way for more criminal activity. Of all his connections, he seemed to be most fond of telling about how he enjoyed his bootlegging partnership with Joe Kennedy during the Roaring 20′s.

If it is true, then there’s really no cause to say that the Kennedy fortune was built on bootlegging, and realistically, probably not even a small fraction of it came from bootlegging. His legal business deals trumped any possible lucrative deals made with the Mafia. However, we know that with all successful businessmen, they keep many irons in the fire, providing many streams of revenue. Is it unthinkable that the father of the most famous political family in the country was involved in the illegal selling of liquor during Prohibition? If it is indeed just a myth, then it is one that surely enlarges the legends of the Kennedy Family.

Tags: Bootlegging, History, Kennedy, mafia