Bobbie Arnstein was awarded a role as Hugh Hefner’s personal assistant for her passionate loyalty to the Playboy tycoon, and this was put to the test when she was convicted of drug offenses
Hugh Hefner’s personal secretary remained loyal to the Playboy founder even when she was arrested for drug offenses and warned that a blow was being inflicted on her life, betrayed by a former girlfriend.
Bobbie Arnstein had come to Playboy as a secretary straight out of school and had dated Hefner for a while before working her way up to his personal assistant.
Featured in the Power: Hugh Hefner podcast, Bobbie was described by her close friend Keith Stroup as the “gatekeeper” for Hefner and was constantly on call for her boss.
“She could sleep a few hours, but if he needed something he called her and in three minutes she would be back around the corner at her desk,” Keith suggested.
The podcast host Amy Rose Spiegel continued, “Bobbie’s duties were limitless, but they all boiled down to keeping Hefner happy. Whatever he wanted and whenever he wanted it, she would find a way to do it. ”
However, when Bobbie was arrested for drug offenses, her commitment to the Playboy founder came under heavy pressure.
When the so-called war on drugs was well underway in the early 1970s, Amy claimed that Hugh Hefner’s name was on then-President Richard Nixon’s list of political opponents.
When Hefner publicly endorsed the legalization of marijuana, prosecutors began investigating whether the Playboy could be linked to drug offenses.
In 1971, Bobbie had traveled to Miami with a friend who was involved in the drug trade. She was arrested three years later and charged with conspiracy to sell and distribute cocaine.
Despite allegedly not involved in any transaction, Bobbie received a 15-year preliminary sentence, more than twice that of her boyfriend.
Keith, speculating, suggested that prosecutors ultimately wanted to bring down the Playboy empire by convicting its infamous founder of drug offenses.
“They felt that if they put enough pressure on Bobbie, they would have to attack Hef and they would have their big celebrity culprit,” he claimed.
And Keith recalled that this went so far that Attorney General James Thompson warned Bobbie that her life was in danger.
“[James] advised her that there was a contract about her life and when she said, ‘who should this be from?’ They suggested, ‘You shouldn’t trust your friend or foe,’ ”Keith continued.
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“Obviously they indicated that Hefner or his allies had a contract with Bobbie. That’s absurd. Hefner wasn’t an idiot, he was quite a cultivated man, he had no weapons and the like.
“But so much were they ready to squeeze Bobbie to try and get to Hef.”
Despite the pressure she was under, Keith revealed that Bobbie was very loyal to Hefner.
“There was no way she would incriminate Hefner – even if there had been a basis for it, she wouldn’t have – but there was no basis for it.”
Tragically, after receiving the jail sentence, Bobbie booked a hotel room under an assumed name and committed suicide.
The morning after her suicide, her former boss held a press conference in which he attacked prosecutors, saying, “Because of her connection to Playboy and me, she became the focus of a cocaine conspiracy case in which she appears to have been widely involved.”