From the archives: The Life and Death of Bobbie Arnstein. Published August 15, 1975.
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, lately 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.
Bobbie Arnstein could never understand garbage. She would repeatedly screw up her face at the people who tried to hand it to her and inquire what it was. Teeny, tiny Bobbie, of the Jean Shrimpton face and Bianca Jagger wardrobe came on with the funny looks every time some corporate hotshot at Playboy refused to authorize a $10 raise for a mansion houseman.
Upon demand, the thousand points would be deducted from her score, even if she was far and away the frontrunner in the game. People who played with Bobbie had better play fair because she wanted to know exactly what she really earned. Bobbie Arnstein wanted to get it right. That’s all. Clowning around was a cover for Bobbie. It softened the things that really hurt. When she complained about her salary and title to Hefner, he always laughed. She was hilarious when she argued that she was a specialist in the organization. That she understood his moods, his prejudices, his makeup better than anyone else. That she wanted to be paid the salary of a specialist; a salary that would let her know that she was important to him.
“Even I watched that figure. We had an old apartment with along hallway and Cynthia would walk from the kitchen down to the living room and I’d watch. She’d come over sometimes, and in those days the girls didn’t wear bikinis much, but Cynthia wore a bikini, and they’d go down to the backyard to sit to sun themselves and I used to say, ‘Cynthia, if you’re going to wear that here, Everybody in the neighborhood is going to be over here.’ And I used to watch her go down the hall.
Bobbie Arnstein acquired a mentor, Nancy Ruffilo, Hefner’s private secretary. “She’s smart,” Bobbie said excitedly to her mother. “Nancy knows everything.” Nancy knew she didn’t want to work at the mansion, anyway. When the inevitable summons came Nancy opted to stay at the office. She sent the next best thing. Bobbie became Hefner’s social secretary in 1962.
It never occurred to anybody that Bobby Arnstein might be capable of, probably was in fact, doing, the job Rosenzweig had been transplanted for. But, it was the Golden Age of Playboy and there was plenty of room at the top. Bobbie was Queen of the hippest high society Chicago ever knew. She should have been satisfied. The quite likeable Rosenzweig became her ally and friend. Bobbie shrugged it off, figuring she couldn’t handle his work even if Hefner would have accepted her in his place.
For nearly a decade the twins spent every summer in the country with their mother and weekend father and every school year at Darwin Grammar School. They took elocution lessons when they were five. It kept the pair in popular demand. The South Haven kids held shows for their folks. Bashful Eddie would shy away from the microphone. His more aggressive sister would pull him by the ear forcing his mouth against the instrument. “Now talk!” she ordered.
The two babies were very close and interdependent. Eddie would stand up in class and ask, “Bobbie, where’s this?” “Bobbie how do you do that?” They finally had to be separated in school. After Dr. Arnstein’s death Eddie’s grades began to fail and Bobbie began to emerge as the stronger of the pair, at least academically. “No, I can’t do that. I can’t leave my brother,” was Bobbie’s answer when her sixth grade teacher suggested that she skip a year. The principal called Mrs.
Bobbie began to retreat from her peripheral position in high school social circles. She was working part-time at a downtown shoe store and looking and acting different from people her own age. She didn’t want to see anybody from Lakeview, much less go out with any of the boys from there. Instead, she dated men she met at work. The late hour sessions where Bobbie sat at the foot of her mother’s bed and recounted her date that evening became more sporadic and less informative.
Bobbie took over the driving in Kentucky. She hit a bump along the side of the highway and the car veered off the road. Bobbie was thrown from the vehicle, but Tom retained trapped in the car. The Volkswagen flipped over and crushed him to death. Bobbie was rushed to a hospital in Louisville where they treated her for severe whiplash around her neck, some minor head, back and leg injuries, and a broken arm. She was also treated by a psychiatrist during her four day stay at that hospital.
No big romances after that, just men fading in once in a while. Bobbie would try people and discard them. “Something that would start out as a romance would end up in a friendship,” Shirley Hillman says. “She considered herself a nonsexual being, so even though she would pretend the pose of sexuality, in the end she would be just downright herself. It’s not usually the kind of thing that men find romantic about women and she found all that kind of pose extremely phony.
The subtle machismo that prevailed at Playboy was getting on Bobbie’s nerves. By the late sixties Bobbie was avoiding men in the organization, she preferred the company of outsiders: a lawyer, a stockbroker, a newspaper columnist. “Her own social situation changed relative to me and the house in the last couple of years,” says Hefner.
A mansion on the West Coast had become part of the Playboy properties, Hefner had begun to spend a lot of time here and Bobbie would shuttle back and forth. Wandering around in the shangri-la atmosphere was an experience she seemed to relish. It was certainly something unique for a born and bred city-girl noted for her hyperactivity. At thirty-plus Bobbie was taking up with men five and six years her junior.
Matthews was being watched by federal agents. Wiretaps were placed on a phone where Ron Scharf was living part of the time with Ira Sapstein . The conversations implied that Bobbie had buyers for the cocaine, though she later confessed to friends that she would have said anything in order to hang onto Ron. He was already showing a conjugal interest in another girl. In November of that year Ron sold some coke to a federal informant. An indictment was handed down and Bobbie’s name was not on it.
Bobbie appeared to be coming out of it. Shirley breathed a temporary sigh of relief, but she knew that the time was only borrowed. Shirley urged Bobbie to take the stand in her own defense. To say anything she had to say to get off. Bobbie refused, she wouldn’t implicate anyone, especially not Ron. For a while, Bobbie was confident that justice would prevail. Confident that she wouldn’t be convicted because she wasn’t guilty. The headlines her arrest merited grated on her. Though she was one of a handful of defendants, she was the one who made the news; it was her picture that ran with the stories.
The eight week trail began. The prosecution’s case was based mainly on the wiretap and the testimony of George Matthews Bobbie depended mostly on character witnesses. She again declined to go to on the stand. She knew she would have to face cross-examination. Subpoenas were issued the following week for Hefner, Bobbie, Ron Scharf and Mary O’Connor, among others. Bobbie couldn’t see the end of the legal hassles. She feared she might be given the choice of immunity over a jail sentence. In that case she would have to take the jail sentence and, she told her friends, Bobbie Arnstein would never go to jail.
The Sunday before she was scheduled to leave Bobbie went over to Shirley and Dick’s north side apartment for dinner. They shared a pizza and talked about parties. “In a large group Bobbie would move around from this person to that person to that person, and carry on three conversations at once. We were talking about how Shirley acted differently. How she would concentrate on just once person,” Dick says. About 11 o’clock, a stockbroker friend and ex-boyfriend picked Bobbie up.
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