Weird History
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The FBI Sting That Made Hef's Assistant Kill Herself Almost Brought Down Playboy

Updated October 2, 2020 16.0k views10 items

On January 19, 1975, Bobbie Arnstein, Hugh Hefner's executive secretary, was found dead in a hotel room. She had committed suicide by overdosing on pills, leaving behind a succinct suicide note and an angry and distraught Hefner.  

Arnstein struggled with suicidal tendencies, but Hefner believed these were exacerbated by an FBI "witch-hunt" against the Playboy empire that resulted in Arnstein's arrest for cocaine possession. Arnstein was not the first Playboy employee to die – and not the first to commit suicide, either – but her story is tragic, not only for the fact that she protected her employer with her dying breath.   

  • Her Arrest Came At The Worst Time For Playboy, Which Was Under Attack From Nearly All Sides

    Arnstein's eight-week trial came at the worst possible time for Hefner and Playboy, and she knew it. Her name was splashed over newspaper headlines everywhere, drawing unwanted attention to Playboy, which was already in the midst of multiple scandals. A Black employee was filing a discrimination lawsuit against the company, which was simultaneously being investigated by the IRS. The icing on the cake? President Nixon had put Hefner on his list of enemies. 

  • Arnstein Had Become Increasingly Paranoid – For Good Reason

    After being convicted, Arnstein was released while she waited to appeal. Directly after, the US attorney for the northern district of Illinois told Arnstein that someone put a hit out on her life. Laura Smith, writing for Timeline, claims the attorney "was trying to scare her into his protection so he could use her for his purposes" by putting her in fear for her life. 

    Arnstein returned to the Chicago Playboy mansion rattled and paranoid. Hefner and everyone else in the mansion feared they were being set up. Hefner swept the place for bugs and drugs that may have been planted, and everyone was a suspect.   

  • Arnstein's Suicide Note Defended Hefner As A Wonderful Boss

    "This is another one of those boring suicide notes."

    That was what Arnstein labeled the envelope that contained her suicide note. In her note, she continued to protect Hefner with the same vigor she did in life. She wrote:

    "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." 

  • The Scandal Surrounding Arnstein's Arrest And Suicide Nearly Collapsed The Playboy Empire

    There were many different reactions to Arnstein's death and the role Hefner and Playboy played in it. Most journalists agreed with Hefner's criticisms of the feds being unfair toward him and his company. The Chicago Tribune, however, accused Hefner of using Arnstein's suicide to perpetuate his own agenda. Whatever the reactions, the negative press was not good for the company. Board members left Playboy, and its stocks dropped dramatically.