Hugh Hefner Politely Declined Chicago Mob Overtures in Both Windy City and Sin City

The powerful Chicago mob twice made overtures to partner with Hugh Hefner and his Playboy clubs, including one in Las Vegas, Hugh Hefner revealed. Both times, Hefner said, he "politely declined."

10 years ago, Hefner, in Las Vegas for his 81st birthday weekend celebration at the Palms, told me the Chicago mob "very much wanted to invest in the Playboy Clubs." The first contact came during a Playboy party when Marshall Caifano, "a heavy hitter in the Chicago mob ... collared me during a party and said he wanted to talk with us." "I kind of backed away and said I didn't want to talk about business in a social setting. So he made a date to come over the next afternoon, and I sat down with my guys and said, 'What do we do with this guy. We can't be doing business with the mob.'" Hefner said he told Caifano, "'I don't know what kind of business you are in,' and he got kind of flustered and embarrassed and said, 'Gambling.' I said, 'Well, you've got your enemies and we've got ours, and I think it would be a big mistake to combine the two.'"

Later, reps from the mobbed-up Chez Paris, "probably the most famous nightclub in Chicago," said Hefner, leaned on him to collaborate on a club in Las Vegas. Again, Hefner held his ground.

Thanks to Norm!