Part of a 40-week series in which we take a look at a specific year in Chicago history via the pages of the Reader.

August 15, 1975

The Life and Death of Bobbie Arnstein

In his day, Hef was a Chicago media personage very much like Oprah is now—someone familiar but mysterious who filled our longing heads with the secrets of the well-lived life. By 1975 there was still a Playboy Mansion in Chicago though Hefner only occasionally occupied it, and you could believe the powers that be sniffed weakness now and decided to take him down. A talented writer turning to the Reader with a story she was busting to tell—that was this paper’s formula, and on August 15 it welcomed Pat Colander. Her tale began . . .

Jay Gatsby never had days like this. At least not in front of Nick Carraway. And at the very least not in front of the Chicago entourage, United States of America Press Corps. Yet here was Hugh M. Hefner, super middle class man, largely given to touting himself as a direct descendant of the F. Scott Fitzgerald antihero, looking very uncool. This Hefner was enough to make any public relations guy cringe. Not to mention the lawyers, who had already been politely told to go to hell.

They hadn’t seen him this shaky and sweaty since the time Dick Cavett pitted him against a couple of women’s libbers and a handful of studio audience hecklers. They’d never seen him so physically drained or so visibly harried. And all the cashmere-coated lords and ladies of gossip, all the suited-up, checked-out network people, all the wet-behind-the-ears city desk reporters foaming at the mouth for a line story, all the newsfeature types scribbling notes about his clothes and the Gallo sculptures around his near north side castle, ate it up and spat it out.

Hefner accused the accusers at the office of U.S. Attorney Jim Thompson of murder. He claimed they manufactured a drug charge against one of his people in a calculated effort to get to him. In the palace hall that screamed party time, the self-crowned pleasure prince screamed that the motherfuckers had killed his secretary and friend, Bobbie Arnstein, whose body had been found in the Maryland Hotel the day before. A sealed envelope on the bedstand was marked: “This is another one of those boring suicide notes.”

The fans went wild. A bloodthirsty public (that’s the same public that played Richard Anthony to Hefner’s publishing operation for 20 years) chuckled that old Bunnyman looked like he was on something himself. That was the cruelest part. That’s what Bobbie Arnstein was trying to avoid by writing what amounted to a press release for Playboy Enterprises as her last act on earth. Friends could almost see her pacing around in her little white office after the scene in the main room, shaking her head and asking, “What is all this shit anyway?”