SINATRA & KENNEDY — Harvard Kid Needed Hoboken’s Help

There was a time, not so long ago, when celebrity endorsements actually carried weight in a national Presidential election…

In the late 1950’s, Frank Sinatra had the world on a string, basking in the glow of his Oscar win for From Here to Eternity and reigning as “Chairman of the Board” while the Rat Pack was in its absolute heyday. But Chairman wasn’t enough—Frank wanted his hands on the Presidency.

He genuinely saw a lot in John F. Kennedy. He saw progressive ideas on civil rights, and he saw the ascendancy of Irish-Catholic Kennedy as a trail being blazed for other sons of immigrants—a storyline that resonated with a skinny kid from Hoboken. Most of all, he saw someone with star quality.

Kennedy on the campaign trail

Sinatra went all-in on Kennedy, enlisting the full sway of the Rat Pack… as well as “other” influences. The Kennedy family—which itself courted celebrity—was more than happy to take the support from Sinatra. As author James Kaplan states in his voluminous biography Sinatra: The Chairman (Random House), patriarch Joseph Kennedy, “…wanted organized crime’s help in rallying organized labor behind his son.”

Frank’s ties to organized crime went well beyond legend. In 1962, Frank Sinatra joined Dean Martin and Sammy Davis, Jr. for an extended gig at the Villa Venice, in suburban Chicago—a nightclub that happened to be owned by one Sam Giancana, the smoking gun to Sinatra’s reputed Mafia connections.

Dean, Sammy and Frank tearing it up at Sam Giancana’s Villa Venice – 1962

The shows at Villa Venice were supposedly payback for Giancana delivering Illinois to John F. Kennedy in the 1960 Presidential Election. Playing two shows a night for eight straight days, the core members of the Rat Pack played up the boozy lifestyle for which they were known, delivering a bawdy cocktail of music and comedy.

As for Kennedy, he infamously met his tragic end in Dallas, Texas on November 22, 1963. Whatever role Sinatra’s “other” influences played in that dark day remain the subject of intense debate.

But Frank truly cherished his relationship with JFK, while it lasted…

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