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.

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, decked-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, at 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?”

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.

You’re being outrageous, Bobbie,” the man making twelve times the amount of the valet, or the chauffeur, or the waiter, or the security guard would admonish her. “He has to have a $4.50 raise.” The poor, deluded girl couldn’t understand all this bickering over five lousy dollars.

Small injustices, they bugged her; big injustices, they preyed on her. She was positively stupid, some say, when it came to that silly pinball machine. The scoreboard had a tendency to roll over too fast when the game room sessions stretched to six and eight hours. The machine would take it upon itself to tack a hundred or a thousand pints onto a score already well into six figures. Bobbie’s fellow flippers were inclined to let it go by, if they noticed it at all. But it was not Bobbie Arnstein’s style to acquire points she didn’t deserve. Sure the amount was trivial, but you couldn’t just let it slide by.

You couldn’t, because pint-sized Bobbie would stand up there in her platform boots, her leather vest, her feathers and beads and get just plain, full tilt righteous.

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.

The waiter—like the restaurant where he worked—was genuine transplanted Indian from Gandhi country. He couldn’t get it right either. Not being very heavily into the English language, it was a tough time taking food orders from the eight people at the table. He stammered his way around to Bobbie who stared at him thru large tinted lenses. “What would you like, Sir?” he made the mistake of asking with some confidence.

Bobbie moved one hand to pull open the left side of her shirt, revealing the fact that she was braless. With the chewed-up edge of the middle finger on the other, she forced his attention on some lackluster cleavage. By the time she was 34 years old, Bobbie had become accustomed to the hysterical laughter she got following the performance of some social outrage.

Being funny at the expense of this poor, bumbling steward wasn’t really a very nice thing to do. Why would not-so-big, not-so-bad, brainy Bobbie, assistant to the president of Playboy Enterprises, main lady of Hugh Hefner’s 74-room Chicago mansion, want to pick on some puny water? She was making him bear the butt of her joke because he had done the one thing she couldn’t tolerate. He hadn’t gotten it straight—the Anglo-Saxon vocabular difference between men and women. In Bobbie Arnstein’s line of work, you were reminded of the difference alot.

Clowning around was a cover for Bobbie. It softened the things that really hurt. (You should have heard her tell the one about the drug arrest. It was a regular riot.) 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.

She wanted a title that would define her 24-hour-a-day duties more accurately than the words “executive secretary” did. But after more than a decade of living within breathing space of her boss, Bobbie Arnstein was unable to come right out and tell him. And everyone else was slowly going deaf on the subject.

Hefner could fix it. Hefner could make it right. But this gigantic publisher of a man who parlayed $600 into a fortune because he knew what every American male wanted, couldn’t see that his baby wanted some of the same. She required a monetary pat on the head, a paper reassurance that he needed her.

She wasn’t getting either. That’s one of the reasons she tried to kill herself the first time.

Cynthia Maddox was a beauty. She was a beauty at Lakeview High School. She was a beauty when she went to work for Playboy—before Bobbie did—as a combination receptionist, model, bunny and company promotion gimmick girl. Cynthia didn’t have to try. Her looks might have been less enduring than what Bobbie had to offer, but they were more valuable to a company not long on need of intelligent women. Bobbie Arnstein took on a job that would present her with a daily reminder of her own deficiencies. She even took a small apartment on Dearborn Street with Cynthia. Bobbie’s way of coping with a jealousy she couldn’t rationalize was to confront it, to accompany it, to live with it, to try and conquer it. Bobbie wanted to get it right.

“Of course we were all in awe of her beauty,” Bobbie’s mother remembers. Cynthia and Bobbie would come to dinner at the Arnstein’s on Friday nights when they were first living together. Sometimes the girls would sun themselves behind the building where Bobbie’s family lived.

“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. Even I used to watch her. I never saw such a figure. The most gorgeous figure that girl had. Bobbie used to say, ‘She’s so pretty. She’s so much prettier than I am.’

Hefner was working at breakneck speed then. His girly picture book was becoming a literary forum. Plans for book projects, real estate acquisitions, other magazines, claimed his time. The Playboy Philosophy—one of the few philosophies without a death clause—was born then. The operation’s pivot point seldom slept and never went home. Hefner made his office on the fourth floor of his living quarters.

The sheer proximity of a bright, attractive woman in his outer office eventually commanded some attention. Bobbie was, for a short time, a social companion. Hefner describes it as having dated some. bobbie would later give a more specific explanation. Everybody knew that Hugh Hefner never just “dated.”

Like some wild dream, some mass hysteria, the greatest of modern adventures lunged ahead, taking bobbie along for the ride. In 1960, Hefner acquired the house at 1340 N. State Parkway. The original idea was for him to get away from the office once in a while. Like most of the ideas he was having at the time, it worked out well. Now, instead of living in the office where he worked, he was working in the mansion where he lived.

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.

Cynthia and Bobbie took a new landlord. The Great Provider Hefner had sustenance for all seasons. Their subsidized apartment in the house was just down the hall from Bobbie’s office. Cynthia, still the great beauty, had landed the big fish. She was now well-ensconced as the boss’ main girlfriend; a title she’d hold for about four years. Empire became a popular synonym for Playboy. The house got hectic with parties and decorated with celebrities. As Hefner’s yeah or nay became worth more and more dollars, Bobbie’s occupation got more and more occupying.

She found herself screening requests, rectifying emergencies, holding temperamental hands, digging up interesting monopoly partners when Hef fancied game-playing at odd hours. If a financial disaster could be averted by Bobbie’s getting an answer from The Man, she’s sit with him until he was ready to talk. As a diplomat, Bobbie Arnstein made Kissinger look tired. She was pitifully exhausted and disorganized but she always broke the tape at the right time. Bobbie Arnstein was Hugh Hefner’s umbilical cord to a business that had grown to be bigger than he was.

Enter Dick Rosenzweig, a dynamic corporate climber who had been moving steadily upward for six years. As a fledgling, he sold ads for Playboy and the short-lived Show Business Illustrated. He was made assistant to the promotion director, Victor Lownes, and later worked in the editorial section as a director of special projects and book projects, then after syndication and production of Playboy After Dark. A suggestion made its way up the ranks, across Bobbie Arnstein’s desk, that the post of executive assistant to Hefner be created. Rosenzweig got the job and established an office in the mansion in October, 1963.

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.

Her lack of self-esteem was beginning to show. “She could have done my job a hell of a lot better than she thought she could,” Rosenzweig said. Bobbie had a corner on the market as far as being a capable assistant to Hefner, but she considered herself incapable of doing anything else. The low opinion Bobbie Arnstein had of herself became apparent to the people around her. Feeling that she was at the pinnacle of what would be her career at Playboy didn’t help. Constantly comparing her own body to the thousands of pictures of naked women that crossed her desk on their way to Hefner’s quarters didn’t help either. But Bobbie Arnstein was never too nuts about Bobbie Arnstein.

Bobbie and Eddie Arnstein were the cutest things to hit Kedzie Boulevard since the suburbs of Chicago. Logan Square neighbors all knew the twins—a true distinction for their mother Evelyn—and for years they were the victims of severe doting. As an added attraction, Bobbie and Eddie spoke with a German accents,t hanks to the superior coaching of a fraulein hired to help around the house. “I’m twersty. I vant vater,” they’d say in their biggest two-year-old voices. “They couldn’t say cat and rat and bat,” their mother remembers. “They used to say cot and rot and bot and one day Bobbie said to Eddie, ‘I could say cat.” She told Eddie, ‘You say cat,’ and he kept saying cot. After about three or four times at this he got disgusted and said, ‘Well I could say pussy.’ I never forgot that little thing it was so cute.”

Evelyn and Alvin Arnstein had their first child, a son, Donald in 1930. They lost a baby girl before the twins were born ten years later. Bobbie’s father, who was by then heading up a lucrative dental practice, was delighted by (and partial to) his new daughter.

For nearly a decade the twins spent every summer in the country (first at Hudson Lake, later in South Haven) 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.

Bobbie was earmarked to be a regular Jewish American Princess. She danced. “You know, she’d get up and do bumps and grinds and things. Where she learned this, I don’t really know,” her mother said. When she was nine Bobbie had taken a year of ballet and was enrolled in modeling school.

When Bobbie and Eddie were 10, their 49-year-old father died of a cerebral hemorrhage. Though he had been warned about high blood pressure, Dr. Arnstein remained active. “They were very emotional children. Whether they had always been emotional and this was just the climax that brought it out of them, I don’t know.” The twins took it very hard. They seemed to withdraw.

Shirley Hillman, Bobbie’s best friend at the time of her death, said Bobbie claimed that she didn’t remember her father. That she had been to young at the time. But Shirley never believed her.

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. Arnstein to school and explained that it wasn’t fair to Bobbie or Eddie for her to remain behind. The children had a long talk and Eddie urged Bobbie to go ahead. She did.

The money ran out a couple years later. The Arnstein’s moved into an apartment on Aldine with Evelyne’s mother, sister, and brother-in-law. The relatives, plus a three-time-a-week maid, gave the kids a grand total of four mothers, and very little male attention. Evelyn Arnstein regretted the move later.

When the time came, Bobbie dated a lot. She went out with many of the boys nobody else would have. Boys that were too short. Boys that were non-athletic or not considered attractive. As long as they were “good company” she said. Adolescent whim got the better of Bobbie when she was a high school junior, she and her girlfriend Denise York spent an afternoon making each other’s hair platinum blonde. Schoolmates were aghast—they hadn’t seen anything yet.

During her senior year, two male teachers discreetly called Bobbie to the office. They confronted her with a picture appearing in the current Playboy; the girl looked exactly like Bobbie. “I tell you. I could not tell the difference,” her mother said. The woman pictured had on a blue shirt with part of one breast exposed. The teachers didn’t believe Bobbie’s denial. They wanted an explanation. They wanted to know why she was taking her clothes off in public. Mrs. Arnstein had to testify to Bobbie’s innocence. There was an angry scene. Eddie kept that picture in his wallet for years afterwards.

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. High school graduation meant only relief, like an alarm clock escape from a bad dream.

Joining the labor force made Bobbie an official adult; moving away from the omnipresent grandmother, mother and aunt was a further liberation. Though Bobbie’s mother still considered their a close relationship, she was seeing her laughter less and less. When her mother warned that living and working in the same place could become a grind, Bobbie ignored the advice.

Hefner and his current sweetheart, the bunnies living in the house dormitory and whoever else happened to be a mansion fixture at the time, became Bobbie’s surrogate family. She would return home now and again, dragging a special boyfriend to meet the folks.

An eligible man had, in the meantime, walked into Evelyn Arnstein’s life. Bobbie was getting pretty hot and heavy with Tom Lownes about the same time her mother was managing the new romance. Evelyn was honeymooning in California when she learned that Bobbie had been in an auto accident.

Tom Lownes was in on the ground floor when Show Business Illustrated was launched by Playboy in April of 1961. He was first named a contributing editor and later imported from the Miami Herald as a full-time employee. With a little help from his brother Victor, Tom went on the payroll the day after Christmas. He met Bobbie Arnstein through what was the normal meshing of personal and professional relationships that characterized the way business was taken care of at Playboy. They began seeing each other regularly. Bobbie’s mother got the idea that it was pretty serious when she saw Tom more than once for dinner.

Show Business Illustrated only lasted through April, 1962, then Tom was named an associate editor of Playboy. Summer was ending for 1963 when Tom and Bobbie set out in a Volkswagen bound for Florida. It was a business-pleasure jaunt; Tom has some personal, ex-wife and children type matters to attend to.

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.

Bobbie was convinced that she had killed Tom. She repeated it over and over again, to her mother on the phone, to her older brother Don who flew to Kentucky with Cynthia Maddox to retrieve her, to anybody who would listen. The doctors were afraid that it would be dangerous for her to be alone and Hefner insisted that Bobbie be brought back to the mansion to mend. He dispatched a limousine to meet the trio at the airport. Bobbie’s convalescence crept along with somebody in attendance at all times. One afternoon Bobbie’s aunt entered the room and found Hefner, outfitted in blue pajamas, picking Bobbie up off the bed.

He turned and explained that Bobbie had been in a great deal of pain, that an ambulance was coming to take her to the hospital. Some people contend that the overwhelming guilt Bobbie felt after Tom’s death ruined her life. That she was never quite the same after she was abandoned by her “one, true love.” Bobbie was in and out of analysis from the time just before the accident until the day she died. But the people closest to her, people who had contact with her everyday, argue that the accident was a blow to Bobbie’s system that shook her up temporarily. She had not been maimed for life.

Lee Gottlieb, promotion director at Playboy, who was a senior editor at Show Business Illustrated, recalls Bobbie breaking down while dancing at a holiday party, saying, “This time last year Tom was here.” He steered her off the floor and over to a cup of coffee. She calmed down 20 minutes later.

Bobbie was drinking too much. “She’d come into parties sort of weaving around,’ according to Gottlieb. Even Hefner noticed that she was overdoing the booze, though it never affected her work. He mentioned it to her. About a year after the car wreck, Bobbie gave up alcohol. The binges stopped as suddenly as they had started. Mary O’Connor, manager of the Playboy mansions, who was hired in the late sixties, said Bobbie found the taste of liquor intolerable. She once complained about a meal’s entree, cooked in sherry, saying it was “too winey.” Marijuana became Bobbie’s infrequent way out.

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. So her relationships would turn into a friendship rather than a passion. A Pitter-pat, she used to call it.”

Pitter-pat. Will you still love me tomorrow? It pained her that she couldn’t play the game. She couldn’t be coy, or hard to get, or pretend that there was somebody else, or refuse on the first date, or do any of those things women are supposed to do to maintain a male attention span. “Bobbie couldn’t reconcile that pain with what she believed stupid. Women that did play that game —the pose and the making up to guys—she found pathetic. She hated it, but she knew it worked. So there she was in the middle of knowing what would work and then resenting people that did it and hating herself for ever doing it. She’d attempt it for a little while and then she’d say ‘Fuck it.'” That was her philosophy and method, so says Shirley.

Homosexuality didn’t work either. “Intellectually, Bobbie could handle a woman loving another woman,” Shirley says. Bobbie Arnstein and Shirley Hillman were in love. In love to the point that Shirley’s husband resented the amount of time Shirley spent with Bobbie. So in love that they talked endlessly and daily. “I never thought that I could love anybody the way that I could Bobbie⁸more than I could love my children.

The two discussed becoming lovers. Bobbie had tried it at one point, very early on, with someone else, but the idea of looking into another woman’s eyes and saying oh darling, and kissing her, just made Bobbie break up. She could not have been the aggressor in a lesbian relationship—she couldn’t even be involved without laughing—so she never bothered to try.

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. “There was a raising of my own consciousness related to women’s liberation and certain kinds of chauvinism that we’ve all been guilty of for years, but not aware of. I indicated that if male executives could bring their girlfriends into the house for various social events—Sunday movies, etc.—that there’s no reason why she couldn’t bring her boyfriends. But that wasn’t until sometime in the ’70s.”

The fat period. By 1969, Bobbie was carrying almost 140 pounds on her five foot three frame, an acquisition roughly akin to contracting the bubonic plague. But she loved food; the menus dished out at the mansion were fabulous, and her mother would subsidize them with occasional pastry. Browns, blues, blacks; she wore anything she thought would hide it. Bobbie’s wardrobe seemed pretty blah when Shirley first encountered her. “She wore this two-piece navy blue outfit almost constantly. I used to think, ‘My God woman, don’t you have anything else to wear?'”

Disgusted with herself, Bobbie checked into a Texas fat farm for a month—it was the first and only time she was away from Playboy and the company for a long period. “It was a place that had kind of a monastic quality about it,” she told Hefner. “Where you weren’t able to talk to anybody. There were no telephones, no radio or TV and you didn’t talk to anybody else in the place for a solid month. It was primarily a water diet and a limited natural foods kind of thing. When she came back she was very high on natural foods stuff.”

When Bobbie returned to Chicago in mid-1970 she had shed almost 40 pounds, was neglecting her once-in-a-while cigarette, wouldn’t touch liquor or dope and got to be rather a pain in the ass to the kitchen about special foods that she wanted to eat. She looked great, she was kicky, her clothes were fun, even weird. Bobbie chucked her complete pre-fat farm wardrobe, it filled 30 cartons. She did frenzied shopping, picking up scads of three-inch platform shoes, denims, belts, feathers, scarfs, chains, jewelry.

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. She made sarcastic remarks about young, hard bodies, but what she was really into was the possibility that they might accept her honesty. That their consciousnesses were malleable.

But all the super-exuberance, the zealous approach to life was a sham. Bobbie Arnstein made the decision to die as early as 1970. Life was very painful. After nearly a decade in analysis she didn’t know why she found things unbearable. Maybe, it was because her mother was right—she would never be Cynthia Maddox beautiful. Maybe, she could blame her dead father for leaving her. Maybe Hefner, who provided her with all the trappings of security minus the emotions of security, who waited for Bobbie’s knight in shining armor to solve her problems, was at fault. In fact, it was Bobbie herself who became convinced somewhere along the line that she should be a woman who could love men despite their weaknesses, a woman who wanted children, a woman who could take the role of dependent and wear and want it, a woman who could be subordinate. Bobbie Arnstein wasn’t any of those things. And she couldn’t stand that she was and what she was not.

Bobbie meet Ron Scharf in a dress shop in the summer of 1971. He was about seven years younger, a part-time street dealer with “beautiful, sensitive hands.” Bobbie was very fond of Ron.

Shirley and Dick Hillman were then in Florida, but Bobbie spoke to them daily. She told Shirley about this great guy she’d met, how they had been seeing each other a lot in the past few weeks, how he wanted her to go to Florida for a weekend. Testimony at a later court trial suggests that Ron went to Florida during the week prior to his trip with Bobbie. He made a deal with George Matthews for six and a half pounds of cocaine, but he didn’t have any money. He promised to return on the weekend, when he did, he brought Bobbie along. According to Shirley, Bobbie may not have even known the purpose of Ron’s trip. According to George Matthews’ testimony two and a half years after he fact, Bobbie stuffed the cocaine into her purse and presumably carried it back to Chicago. That was September, 1971.

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 other part of the time Ron was living with Bobbie in her apartment in the mansion). 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 was brought in for questioning, but made it clear that she would not cooperate. She and Ron continued to see each other.

Her wheels were spinning. Bobbie was beginning to feel like a closeted beast. With Hefner spending at least half his time in California, Bobbie felt more and more useless. She revived the old idea of taking another job at Playboy, maybe an editorial job. Rosenzweig pointed out that her salary was a problem, that she was making way too much to go in as a trainee for a magazine job. He suggested that she buy some property. Get out of the house, her womb, her jail. She and Mary O’Connor talked about starting a “country inn”—Mary already had a restaurant business on the side. None of the plans took hold. Bobbie became obsessed with her job problems. She learned the salaries of some other people at Playboy.

One night she retreated back to her apartment, a sort of campy black, dingy alcove at the back of the buildings and took a dosage of barbituates (drugs she regularly used to sleep) that she was sure was large enough to kill her. Bobbie called Shirley to talk, even though it was already quite late. Shirley could tell by the way Bobbie was slurring her words that she had finally done it. Bobbie didn’t want to be saved; she had told Shirley that over and over again. But Shirley couldn’t just let her die, either. She called the staff at the mansion. Bobbie was taken to Henrotin Hospital where they pumped her stomach. She was angry with Shirley. “I thought our friendship was beyond this,” she said. Shirley replied that if Bobbie really wanted to kill herself she shouldn’t have called.

Begin again. Bobbie made plans to move into another apartment. This time she did it all in white, with a lot of green plants around, a hammock, a swinging chair, a lot of life. She redecorated her office in the same optimistic vein. Playboy changed Bobbie’s title to “Assistant to the President,” though her name was not on the magazine’s mast head. She got a raise.

Bobbie appeared to be coming out of it. Shirley breathed a temporary sigh of relief, but she knew that the time was only borrowed.

The Ron Scharf drug case had gotten more complicated. Matthews fled. And, the Playboy people contend, Washington woke up to the fact that Bobbie Arnstein, associate of High Hefner, might be indictable. Douglas Roller, a prosecutor out of the Washington office of the Department of Justice, was put on the case. Federal agents finally caught up with Matthews. They had an iron-clad case against the known drug trafficker. It wasn’t his first offense.

Matthews turned state’s evidence after he was promised a lighter sentence. He implicated Bobbie in a conspiracy to distribute cocaine. A new indictment was brought down on March 21, 1974. This time Bobbie Arnstein was at the head of the list. She was arrested that day carrying a small quantity of cocaine in her purse.

“It came as no surprise to me that she used cocaine,” Hefner says. “But I didn’t know that she used cocaine. What I’m saying is she didn’t use it in my presence and that’s not a surprise. She would know that I would not be happy with it and therefore she wouldn’t do it. Unrelated to drugs, that’s another form of saying that the nature of our relationship—that she wanted my respect—built up kind of a reserve.”

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.

Bobbie felt a lot of pre-indictment and pre-trail pressure. Convinced that they were trying to get Hefner behind bars using something she had to say, Bobbie refused to say anything. She didn’t really know anything they wanted to hear anyway. After a few months the prosecutor’s office believed her. Word was parceled down to Bobbie that Hefner was standing behind her. He contacted her himself. He paid her legal fees. Rosenzweig reassured her. Marilyn Cole, a mutual friend of Hefner and Bobbie, contacted her from London to reiterate the support she was getting from everybody.

But Bobbie knew that Hefner was having difficulty coping with his own lawyers who were urging him to disassociate himself from her. Bobbie was called to the prosecutor’s office. U.S. Attorney Jim Thompson told her that her life might be in danger. He said several good sources had indicated to him that there might be a “contract,” and Bobbie should trust neither friend nor foe. Clearly the idea was Bobbie should place no faith in Hefner, who, whether he knew it or not, had become very much a father to Bobbie. She refused protection.

Bobbie told Shirley that she would do herself in before anybody else got the chance. And she made good her promise by attempting suicide again. Same method, new apartment. Again she called Shirley. This time her friend was afraid of the publicity if she arrived at a Chicago hospital with a drugged Bobbie in tow. She contacted a doctor-friend in Waukegan and drove Bobbie there for treatment.

The eight week trail began. The prosecution’s case was based mainly on the wiretap and the testimony of George Matthews (Bobbie specified in her suicide note that Matthews perjured himself.) Bobbie depended mostly on character witnesses. She again declined to go to on the stand. She knew she would have to face cross-examination.

Ira Sapstein, named on the original indictment but not in the second indictment, resurfaced. In a meeting with his lawyer and the federal lawyers he was evasive. The defense thought he might be able to clear Bobbie. The prosecution thought he was trying to cooperate enough to save himself from future indictment. The judge decided it was a lot of legal nonsense and threw the matter out of court.

Bobbie was found guilty in the conspiracy. The jury believed that she brought the cocaine from Florida to Chicago. The trial also established that she was a social user. On November 26, Bobbie got a conditional sentence of 15 years in prison, subject to review and a probably reduction after 90 days of psychiatric tests. Bobbie’s lawyers had chosen to go for the psychiatric test sentence because they believed there was no hope that they would get probation, even though the probation officer was sympathetic to Bobbie.

Hefner urged her to come out to California, as he had several times during the previous months. Her case was pending appeal. On December 8, the Chicago Tribune ran a front page story calling Hefner the target in a drug probe by the Federal Drug Enforcement Administration. The inquiry was centered around drug use in both mansions. The DEA was also reopening the death of Adrienne Pollack, a Chicago bunny (whom Hefner claims he never even met) who died of an overdose in September, 1973. Bobbie held herself responsible for everything.

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.

Shirley tried to involve Bobbie in plans to start a new life on the West Coast. Over Christmas Shirley sent to California and looked for an apartment where she, Dick and the children, could live with Bobbie. Marilyn Cole, tired of London, made plans to join them in their new home. Rosenzweig reminded Bobbie that the staff was sorely lacking her golden touch. Not only did Playboy want to get her out of Chicago for her own good, he insisted, they genuinely needed her.

But things didn’t seem to be working. Bobbie couldn’t live in the California mansion. She would have to take a hotel room until Shirley could join her. She would have to commute and she didn’t drive. She’d have to work regular business hours and leave at 7:00 because Hefner’s lawyers didn’t want her around. She was worried that this was the organization’s way of gently easing her out.

She wasn’t anxious to face Hefner, whom she hadn’t seen since before the trial. In her darkest moments it crossed her mind that he only wanted her out there because he wanted Marilyn Cole out there. Bobbie knew that it would probably blow over, that it wasn’t as bad as all that —intellectually. In her heart, it was pretty bleak. “She really thought it would change,” Shirley says. So, Bobbie decided t go ahead and move. She was in love with the house and grounds in California and Playboy was too much a part of her life not to give it a second chance.

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. They stopped and had coffee with some people he knew. Then, about 1 a.m., he dropped Bobbie off at the mansion.

On he way to her apartment Bobbie stopped and asked a night houseman for a fifth of some kind of liquor. He said that he had to go get the key for the cabinet and added, “Are you taking it to a party or something, Miss Arnstein?”

Bobbie shook her head and smiled. “No, I’d just like to see what it feels like to have a hangover.” She retreated to her little white apartment and roughed out a suicide note. She wanted to get it right, to set the record straight. ” … Hugh M. Hefner is—though few ill ever really realize it—a staunchly upright, rigorously moral man—and I know him well and he has never been involved in the criminal activity which is being attributed to him now. That is the irony—but I have come to know that innocence is of small significance when compared to the real purpose and intent of the various government agencies engaged in pursuing him and leveling their harassment against me to the masses.”

No one saw Bobbie leave the mansion at about 2:30 in the morning. She checked into the Maryland Hotel about a block and a half away. She registered under the name Roberta Hillman, insuring the fact that Shirley would be able to find her.

Bobbie didn’t take any booze with her; she had just enough pills in her handbag to kill her five times. She called Shirley, presumably after she had taken the pills and before she finished the final draft of her letter. Dick told her that Shirley was asleep, should he wake her up? Bobbie said no, that she would talk to Shirley in the morning.

When they found Bobbie’s body she had been dead for about 12 hours. Nobody who knew her was surprised. Some friends got angry at Hefner, claiming if she hadn’t had to go to California she might not have done it. Others pointed their fingers at the police. Shirley screamed, hid under the blankets and shook. She knew, “Bobbie killed Bobbie.”

Bobbie wanted to be cremated, but good old social norms interfered again. Her mother arranged a Jewish service with an open casket. “I knew it would be a circus,” Shirley said, that’s why she declined to go. “If I had been a stronger person I would have been with her and let her do it and comfort her at the time. I wish we could have gone off somewhere together and I could have been with her as long as she was determined to do this thing.”

When Hefner heard that Bobbie was dead he wanted to talk about it—to anybody who would listen. He made the decision to hold the press conference almost immediately. At the last minute Bobbie’s mother asked him to be a pallbearer.

It was the first funeral Hugh Hefner ever attended.