Excerpt from Hugh Hefner’s First Funeral and Other True Tales of Love and Death in Chicago by Pat Colander


This was the beginning of the end of the sexual revolution. In Chicago.


By January 15, 1975, we were doing what felt good, eating birth control pills, reveling in loose attachments. We had decided on healthy, acceptable levels of selfishness, the only cure for chronic unhappiness, sworn enemy of the free spirit.


Hugh M. Hefner pointed the way.  A cultural leftist who made a career out of being true to himself, he worked hard to ride the crest of this wave and so became a hero. He was a nobody from nowhere, a prophet of the flaunted convention, and finally a billionaire.  The story of how he built his magazine into an enterprise was media folklore, and Hefner was already a living legend.


Ironically, by the mid-70s, some of the heady excitement of two decades of Playboy’s success dissipated, and Hefner, seeking a quick romantic fix, had recently been touting himself as an F. Scott Fitzgerald character.  But he had forgotten the end of the story.



The Press Conference


Jay Gatsby had never had a day like the one Hefner was having that day.  The Chicago press corps saw that Hefner was upset.  His face was contorted with pain.  This Hefner was enough to make any public relations manager cringe.  Not to mention the lawyers, who had already been politely told to go to hell.  He had a few words to say about Bobbie Arnstein, his employee and friend, found dead a day before.


Nobody in the Great Room at Chicago’s Playboy mansion had ever seen Hefner that distraught.  Several years earlier, Hugh Hefner had appeared on the Dick Cavett Show in a confrontation with Susan Brownmiller and another feminist, and the two women had thrown him off balance.  He was vulnerable. But this was different.  Hefner was physically drained and visibly harried, despite the fact that he had not an enemy in the room.


Hefner had always enjoyed an excellent relationship with the press, especially the local, celebrity-starved Chicago press.  Reporters gladly accepted party invitations to the mansion.  Journalists liked his hospitality, his cooperation, and his funding of First Amendment causes.  Hefner was a colleague in a sense to many of the people at the press conference—a couple dozen photographers, scribes and television personalities packed into the auditorium-sized room at the mansion on North State Parkway. The lords and ladies of gossip in their cashmere coats.  The pressed and polished network news guys. The scruffy 20-somethings from the city desk, who knew this press conference could make page one. The special topics writers, “new journalists,” scribbling notes about Hefner’s clothes and Gallo sculptures and the polished wood paneling in the near north side castle.


Hugh Hefner did not disappoint them when he launched into his accusation of murder and blood on the hands of the prosecutors at the office of the U.S. Attorney James Thompson.  Thompson, positioning himself as a tough law-and-order man, already anticipated his win in the following year’s gubernatorial race.  Hefner said Thompson was leading “a politically-inspired witch hunt,” and publicly proclaimed that the federal investigators had manufactured a drug charge against one of his people in a calculated effort to hang a criminal charge on him.  Here in the palace hall, above the dimly-lit swimming pool fashioned into a tropical paradise, next door to a game room with wall-to-wall pinball machines, Hefner screamed that “the motherfuckers” had killed Bobbie Arnstein, whose body had been found in the nearby Maryland Hotel.  A sealed envelope on the bed stand was marked: “This is another one of those boring suicide notes.”


Nobody in the room wanted to see it come to this.  There were reporters and writers who winced and turned away. But there were others who sensed that Hefner’s brand of slick hedonism had reached its zenith, at least for the time being, that perhaps the suave persona was getting old and jaded, that the pendulum was swinging back towards Richard Nixon, Phyllis Schlafly, and Jerry Falwell.  There were journalists who smelled blood, who claimed to have inside information that the U.S. Attorney’s office was indeed after Hefner, and what was more, their leaking sources told them there was evidence against him. The audience went wild over the Bobbie Arnstein business; readers always loved the newspapers when somebody rich and famous got into trouble. Nothing new there.


Undeniably this was a good story.  There were chuckles among the cynics Hugh Hefner had been wining and dining for years. That afternoon more than one person overheard a reporter who said that old Bunnyman looked like he was on something himself.  That was the cruelest part of the whole, absurd tableau.  That was precisely what Bobbie Arnstein was trying to avoid by writing a suicide note, which was tantamount to a press release for Playboy Enterprises as her last act on earth.  Friends of Bobbie could envision her pacing around in her small white office after the scene in the main room, shaking her head and asking, “What is all this shit, anyway?”


That there was a limit to the level of hypocrisy Bobbie Arnstein found intolerable was well-known around the organization.  She was impatient with the bureaucracy that inevitably sprang up at Playboy. “What is this?” she said when presented with a memo, a quick reminder of policy, or something in writing, evidence of growing corporate paranoia. Teeny, tiny Bobbie, with the Jean Shrimpton face and the Bianca Jagger wardrobe, came on with the funny looks when a middle manager refused, say, to authorize a $10 raise for a mansion hired hand or clerk.


“You’re being outrageous, Bobbie,” the person making twelve times the amount of the valet or the chauffeur or the waiter or the security guard or the laundress would admonish her.  Bobbie Arnstein would not argue over a few lousy dollars.  She loathed the mentality of those who would.  Small dishonesties bothered her, too.  She was positively stupid some said, 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 heat up, tacking a hundred or a thousand unearned points onto a score already into six figures.  Bobbie’s fellow players were inclined to let the matter pass, if they noticed. But it was not Bobbie Arnstein’s style to collect points she did not earn.  The amount may have been trivial, but the principle of the thing was not.


She could not just let it go, so her opponents could not either.  Because even if inclined to let it go, pint-sized Bobbie would stand up there in her platform boots, her leather vest, her feathers and beads and get plain, full-tilt righteous. The scorekeeper would deduct the thousand points from her lead, even if she was far and away the front-runner in the game.  People who played with Bobbie learned to play fair because that was the way she wanted it.  She wanted to get it right.  She wanted to tell the truth. That’s all.


A group of Playboy executives and hangers-on were eating at an Indian restaurant one night.  The waiter, a native Indian recently immigrated to Chicago, could not speak or understand English very well.  He stammered his way around the table, having a difficult time taking orders from the eight people.  Haltingly the waiter made his way over to Bobbie, who stared at him through large, tinted lenses. “What would you like, Sir?” he asked with a slight trace of arrogance.  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 her middle finger on the other hand, she forced the waiter’s attention on some lackluster cleavage.  Bobbie Arnstein was 34 years old and was accustomed to the hysterical laughter she got from a group who witnessed her response to some social outrage.


Making a joke at the expense of a bumbling steward in a restaurant was not a very nice thing to do.  And why would Bobbie Arnstein, then the assistant to the president of Playboy Enterprises, the most important woman at the 74-room mansion, want to pick on some puny waiter? He had crossed the line into the world of what Bobbie found impossible, in this case the Anglo-Saxon vocabulary distinction between men and women.


In Bobbie Arnstein’s workplace you were reminded of the differences often.


Clowning around was a cover for Bobbie that softened the things she rarely confided, things that hurt.  When she complained about her salary to Hefner, he laughed because he thought she was kidding.  She tried to argue that she was a specialist in his organization and understood his moods, biases, and makeup better than anyone else.  Bobbie wanted to get paid the money a specialist demanded, she said.  She wanted the amount of money that would signal that she was important to him.


Bobbie Arnstein told more than one of her friends that she wanted a title that would define her 24/7 duties more accurately than executive secretary did. But even though she had been with Hefner for more than 10 years, she was not able to come right out and say what she wanted.  She protested to others that she and Hefner did not have that kind of talking relationship.  And everybody else that Bobbie made her case with was slowly going deaf on the subject.  Hefner could have easily fixed the situation, but the publisher-genius who parlayed $600 into a fortune because he knew what every American male wanted, could not see what this woman needed. And it was a monetary equivalent of a pat on the head, a paper reassurance that she was valuable, possibly irreplaceable to him. She was not getting either, and that was one of the reasons she tried to kill herself the first time.


Bobbie Arnstein used to say that she had not wanted the goddamn job in the first place.  Bobbie was barely older than a teenager when she joined the ranks of the Michigan Avenue slaves. She followed a series of low-paying Girl Friday posts at a shoe store, a car dealership, and a radio station, around the coming posh north end of downtown, where the shopping district intersects the residential Gold Coast. An inauspicious career at Lakeview High School had not prepared her to tough it out in the secretarial pool.  Bobbie was smart and had been steered into track one classes.  Her teachers thought she would make an excellent teacher.  By the time her four years were up, Bobbie Arnstein was sick of school.  If she ever thought of continuing her education, she kept it a secret.


The market was awash with sweet young things in the same exact predicament. But Bobbie Arnstein had a slight edge: she oozed public relations savvy.  She had bleached blonde hair, an infectious smile, and brains enough to act sophisticated—all advantages in the customer service bracket.  A counselor at a local employment agency knew Bobbie was beguiling enough to work at a company with one of the better addresses.


She was first placed at an advertising firm, the most glamorous job immediately available.  She was pretty happy there when the agency called again a few weeks later, urging her to look into an offer at Playboy. “This job is you, Bobbie,” the agency woman insisted. Bobbie was not so sure.  She thought it over and called the agency back.  She did not know if she could measure up physically.  There was a mystique about Playboy, and though Bobbie thought it might be fun to work there she was reluctant to give Playboy the opportunity to reject her.  The employment counselor was adamant, and finally Bobbie decided to give it a try.


At Playboy, Bobbie was well-liked from the beginning.  She was young, fresh-faced, and very pretty.  Bobbie started at $70 a week in September 1960 as a “floater,” an attractive girl assigned to no particular desk or person.  Often she ended up stationed on the fourth floor of the magazine office at 232 E. Ohio Street, the slight, sexy-looking guardian of the editorial sanctum.  But Bobbie was still uncertain about the job, which gave her pangs of insecurity.  One tangible reason: Cynthia Maddox, who was the receptionist on the first floor.


Cynthia Maddox was a beauty.  She had been 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.  Bobbie Arnstein took a job that would present her with a daily reminder of what she considered to be her own deficiencies.  She even took a small apartment on Dearborn Street with Cynthia. Bobbie’s way of coping with a jealousy she could not rationalize was to confront it, accompany it, live with it, and to try to conquer it. Bobbie wanted to get it right.


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


“Even I watched that figure.  We had an old apartment with a long 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 top speed in those days.  His girly picture magazine was morphing into a literary forum.  Plans for book projects, real estate acquisitions, and other magazines, claimed his time.  The Playboy Philosophy—one of the few philosophies without a death clause—was born then. Hefner, always at the center of the operation, seldom slept and never went home.  Hefner made his office on the fourth floor his living quarters.


The sheer proximity of a bright, attractive woman in his outer office eventually commanded his attention.  Bobbie was, for a short time a social companion.  Hefner described it as having dated some.  Bobbie gave a more specific explanation of what she considered a very temporary physical liaison. Everybody at Playboy knew what Hefner meant when he talked about dates.


The money was pouring in.  Like a wild fantasy, a great modern capitalist adventure—that was how Playboy grew.  Hefner and his burgeoning staff surged ahead, and Bobbie was along for the ride.  Some months after she started, Hefner bought a big, brick house at 1340 N. State, not far from the headquarters of John Cardinal Cody, then the ranking official of the Archdiocese of Chicago, one of the largest concentrations of Roman Catholics in the world.  The original idea of the house was for Hefner to get away from the office once in a while.  Like most of the ideas he was having at that time, it worked out better than he expected.  Now, instead of living in the office where he worked, he was working in the mansion where he lived.


Bobbie had acquired a mentor by then.  Bobbie’s friend Nancy was Hefner’s private secretary.  “She’s so smart,” Bobbie told her mother.  “Nancy knows everything.” Nancy knew she did not want to work at the mansion.  When the inevitable summons came, Nancy opted to stay at the office.  She sent the next best person though, and Bobbie Arnstein became Hefner’s social secretary in 1962.


Soon afterward, Cynthia Maddox and Bobbie Arnstein moved in with Hefner.  Hefner was never secretive about how much he liked having pretty girls around, but he was also a benevolent provider known for his generosity.  At the time Hefner was a notorious soft touch, who was always supporting a retinue of “artists” and sycophants who were down on their luck.  Cynthia and Bobbie’s subsidized apartment in the house was just doors away from Bobbie’s office.  After a short time, Bobbie had the place to herself.  Cynthia Maddox became ensconced as Hefner’s main girlfriend; a title she would hold for about four years.  Playboy was most often described as the “Playboy Empire” now.  The house was hectic with parties, filled with celebrities of the moment and a growing number of paid employees.


Hefner, who spent most of his time cross-legged on the famous round bed with a fur cover, talking on the telephone or looking at page proofs, was fighting a battle with the clock.  Large amounts of money were at stake, and he was not good at delegating authority. He ended up making most decisions himself.  His quarters looked more like a data-processing center than a bedroom.  Bobbie Arnstein’s occupation was increasingly occupying.


She found herself screening requests, responding to emergencies, holding temperamental hands, digging up interesting monopoly partners when Hef fancied a game at an odd hour.  If a financial disaster could be averted by Bobbie’s ability to get an answer from Hef, she would sit with him until he was ready to decide.  She was a tireless diplomat.  There were times, her friends recalled, when she was pitifully exhausted and disorganized, but she always broke the tape at the right moment. Bobbie Arnstein was Hugh Hefner’s umbilical cord to a business that had grown huge, bigger than he imagined.


Dick Rosenzweig entered the picture. Rosenzweig was someone you would have called a dynamic businessman in those days. He had been moving steadily upward in the organization for six years.  As a fledgling publishing executive, he sold ads for Playboy and the short-lived, (maybe ahead of its time) Show Business Illustrated.  Rosenzweig then became assistant to the promotion director, Victor Lownes, and later worked in the editorial section as director of special projects and books projects, then in syndication and production of the television show 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 Bobbie Arnstein might be (and probably was, in fact) capable of doing part of the job Rosenzweig had been transplanted to do.  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 had ever known. The quite likable Rosenzweig became her ally and friend.  Bobbie shrugged it off, figuring she could not handle his work, even if Hefner could conceivably have accepted her in Rosenzweig’s place.


“She could have done my job a hell of a lot better than she thought she could,” Rosenzweig said later.  Afterwards. Bobbie had a corner on the market as far as being a capable assistant to Hefner, but she considered herself unqualified to do anything else. The low opinion Bobbie Arnstein had of herself became apparent to the people around her.  Feeling that she was at the peak of what would be her career at Playboy did not help.


Constantly comparing her own body to the thousands of pictures of naked women that crossed her desk on their way to Hefner did not help.  But Bobbie Arnstein was never too nuts about herself….Read the WHOLE story at http://eckhartzpress.com/shop/hugh-hefners-first-funeral-and-other-true-tales-of-love-and-death-in-chicago/




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