He donated to John F. Kennedy’s presidential campaign, he said, because he figured he would be “a Mr. Smith Goes to Washington, Meet John Doe president.” Plus, Kennedy was the ultimate Playboy man—urbane, Ivy League, great-looking, oversexed, a real-life fantasy figure. JFK, Hefner said, “was one of us.” (And as soon as he became president, Kennedy confirmed that, announcing that one of his favorite books was the Bond novel From Russia with Love.)