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

Updated October 2, 2020 16.5k 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.   

  • The FBI Had Been After Hugh Hefner For "Denigrating" American Culture For Quite Some Time

    Photo: BE075403 / Wikimedia Commons / CC0

    Hugh Hefner and the Playboy empire weren't exactly popular with the Federal government. For four years in the 1970s, the Feds attacked Hefner and his empire, only stopping after Hefner's assistant Bobbie Arnstein committed suicide after being convicted on a cocaine possession charge.

    The Feds tried desperately to pin some drug charge on Hefner in order to take down his business, which they believed Hefner was using to traffic drugs. After Arnstein's death, Hefner accused the government, namely US attorney James Thompson, of unjustly chasing him down. Thompson denied these claims, saying that prosecutors did not conduct "headhunting" missions.   

  • The Drug Charges Against Arnstein May Have Been An Attempt At Taking Down Hefner

    After the Feds couldn't get anything specifically on Hefner, they decided to get to him through his assistant, Bobbie Arnstein. The FBI and DEA turned their focus to Arnstein and a man she was involved with, Ron Scharf. They knew Scharf was involved with illicit drug deals and tapped his phone in the hopes that he would lead them to Arnstein, who would hopefully bring them to Hefner. 

    However, the alleged plan backfired when Arnstein, loyal until the end to her boss, refused to testify against Hefner, which probably led to her long prison sentence. 

  • She Was Arrested For Carrying Half A Pound Of Cocaine

    After Arnstein became involved with Scharf, it was a matter of time before the FBI and DEA were on her trail. In 1974, Arnstein was arrested in front of the Playboy mansion in Chicago, along with Scharf and a few other men, for conspiracy to transport half a pound of cocaine from Florida to Chicago. Arnstein was also implicated by George Matthews in exchange for him receiving a lighter sentence, which allowed the Feds to arrest Arnstein, who had a small amount of cocaine on her person at the time of her arrest.

  • Arnstein Was Sentenced To 15 Years In Prison — More Jail Time Than The Men Who Actually Masterminded The Operation

    Although Arnstein was arrested along with a number of others, she was given more jail time than the rest. Scharf got six years – Arnstein got 15. It was believed that Arnstein got the extra nine years because of her refusal to cooperate with the Feds. Arnstein was staunchly loyal to both Scharf and Hefner.

    If it was to be believed that Arnstein was targeted in order to lead the Feds to Hefner, her refusal to implicate him in any wrongdoing probably caused anger among Federal agents, who had been trying to nail Hefner for years.