Keith Stroup tears up when he talks about his friend Roberta "Bobbie" Arnstein, Hugh Hefner's executive secretary at Playboy who took her life in 1975 after being convicted on Federal cocaine-trafficking charges. This all plays out in Ep. 4 ("The Price of Loyalty") of Secrets of Playboy, an eight-part miniseries on A& E.
"Bobbie was my soulmate," Stroup says emotionally. "We were incredibly close. I should have been able to help her, but I wasn't, so I felt incredibly guilty."
NORML founder Stroup met Hefner and Arnstein at a meeting with the NORML Foundation about funding for his nascent marjuana legalization organization in 1971.
Stroup's 2020 article, "Crucial Early Support from Hugh Hefner and the Playboy Foundation," posted at NORML, described Arnstein as "a valuable NORML ally" and "a beautiful lady from Chicago who had at one time been a lover of Hef’s, but who had since become his confidante and personal assistant, handling everything from his most important matters to his least significant matters. At some point Hef grew to depend on Bobbie so much that he asked her to move into her own apartment within the Playboy mansion [in Chicago], and she became a part of the family.
"Bobbie was hip, in an urban sort of way... [she] was on top of the latest thinking on drugs and consciousness, and we ended up spending many evenings getting stoned and discussing our understanding of the universe. This woman was living the life most of us could only dream about. And she was, as it turns out, a real 'head' who loved smoking marijuana."
But it's cocaine that got her and the Playboy organization in trouble. Narcs, sniffing out wanton drug use at the mansion on N. State Pkwy., staked it out and ended up busting Arnstein and two others for possessing and distributing a half-pound of cocaine in 1974.
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Stroup admits to using coke with Arnstein in the mansion, but says Hefner wasn't into it.
"Hefner insisted that she keep a boxful of hand-rolled joints on his bed stand in his private quarters," says Stroup. "I occasionally saw amphetamines. But I never saw cocaine used in the mansion, other than when Bobbie and I would occasionally snort a line of coke from half a gram she had. We were very careful to keep it out of Hef's view or knowledge or anybody in the mansion. I was alerted that if Hef or any of his people ever see or hear about cocaine you will never enter this building again. I think that was a real rule. It wasn't just PR."
Several women who worked for Playboy interviewed in the episode contradict Stroup's contention and claim cocaine and other drugs like Quaaludes were commonly used in the mansion. The episode also focuses on the Quaaludes overdose death of Bunny, Adrienne Pollack, in 1973. She was just 23. Arnstein was 34.
Stroup tells CelebStoner: "I too recognized the different perspectives that some of the women interviewed for the series offered about cocaine use in and around the Playboy mansion, as contrasted to my perspective. I presume Hefner and his friends might have kept some of their activity private from those of us who were not 'family.'"
Thanks in part to Arnstein, NORML received upwards of $1 million in funding from Playboy during the '70s. Stroup, who's remained with NORML as chief counsel and a board member, is forever indebted to her and Hefner, who passed away in 2017 at 91.
In October 1974, Arnstein and the two others were found guilty. She received a conditional 15-year sentence and was released from prison. However, Stroup writes: "On Jan 12, 1975, while she was awaiting sentencing, Bobbie checked herself into the Hotel Maryland just a couple of blocks from the Playboy mansion, where she took a lethal dose of prescription drugs."
Keith Stroup on Bobbie Arnstein: "I should have been able to help her, but I wasn't, so I felt incredibly guilty."
Some on the program believe it was not a suicide, that Hefner and his organization managed to got rid of Arnstein even though she had not turned on Playboy, but obviously knew perhaps too much.
Stroup demurs regarding any conspiracy theories regarding Arnstein's death. "That simply isn't believable to any of us who knew the both of them," he contests. "Bobbie had made it fairly clear to all of her friends that she was going to do what she needed to do to not go to prison, but she wasn't going to flip on anybody in the Playboy empire."
After her death, Hefner described Arnstein as "an already emotionally troubled woman [who was] pushed beyond her endurance and she killed herself" and acknowledged, "There was incredible pressure on Bobbie to make her strike out at us."
With Arnstein death, the Playboy cocaine scandal/investigation of the early '70s simply ended. But thanks to Secrets of Playboy, it's not forgotten.
Still holding back tears, Stroup tries to explain how ambivalent Arnstein was about her work at Playboy. "Bobbie was a feminist," he recalls. "She wanted to be respected for her mind, her achievements and her judgement. On the other hand, she put herself into a world where every woman was a sex object. I think it was the conflict at the center of Bobbie's soul. Bobbie clearly understood that this world she lived and thrived in as glamorous as it was, and it was very glamorous, was also based on exploiting other women. That must have caused some guilt."
Read More About the Playboy-NORML Connection here.
