The Myth of Joe Kennedy’s Bootlegging

Wild parties in Palm Springs with famous actors and musicians, affairs with beautiful starlets, nail-biting showdowns with international rivals, a dramatic death, a hero’s burial: The life and times of President John F. Kennedy are both well-known and well-mythologized.

For decades, JFK was viewed as a prototypical golden boy both in his home state of Massachusetts and beyond. But the truth about his behavior, which has slowly come out over the years, is a good deal less glowing—and a good bit boozier.

His dinners at the White House were legendary for their copious cocktails, including rum & cokes according to Sally Bedell Smith’s book Grace and Power. “They served the drinks in enormous tumblers,” writer and close Kennedy friend George Plimpton told Bedell Smith. “Everybody had too much to drink because they were excited.

And when Kennedy left 1600 Pennsylvania Avenue, his trips to the desert with Frank Sinatra were certainly a chance to unwind and indulge. “It’s not as though the president and Dad would meet to play golf,” Tina Sinatra told Seymour Hersh for his book The Dark Side of Camelot. “I was never, ever there. That was not a weekend you brought the kids into.”

But no matter how many trysts Kennedy had or how much he drank, his habits paled in comparison to his father’s supposed activities during Prohibition.

According to lore, Joe Kennedy built the family’s fortune by bootlegging. Just as George Washington is now known ‬for his rye whiskey distillery and Harry Truman’s love of bourbon famously helped him defeat his formidable opponent Dewey, the Kennedy family was synonymous with East Coast rum running.

The only problem with this story is that none of it is true.

In Last Call, author Daniel Okrent goes into great detail about how he couldn’t find any credible information to support the allegation that the Kennedy patriarch illegally sold alcohol during Prohibition, even though it is now normally treated as fact. ...