'Secrets of Playboy' Details How Hugh Hefner's Alleged Drug Culture Led to Overdose and Suicide

Each week, A&E's 10-part docuseries Secrets of Playboy is delving into the dark side of Hugh Hefner's iconic empire.

The first three episodes largely focused on the ways in which the toxic, often allegedly violent, real-life sexual dynamics at Playboy belied Hefner's vision of liberation and empowerment for all.

On Monday's episode, "The Price of Loyalty," the series turned its focus to the allegedly pervasive drug use at Hefner's mansions in Chicago and Los Angeles. It chronicled how the mogul's thrall over the people around him created a dangerous environment that led to the criminal conviction — and death — of his social secretary, 34-year-old Bobbie Arnstein.

And while Arnstein was found guilty of a crime, A&E does point out at the end of episode 4 (and all episodes of Secrets of Playboy) that the series "contains allegations of wrongdoing over decades by Hugh Hefner and others associated with him. The vast majority of allegations have not been the subject of criminal investigations or charges, and they do not constitute proof of guilt."

Bunnies or Mules?

Not long before Bobbie Arnstein's death, Hefner and Playboy were confronted by tragedy when Bunny Adrienne Pollack died of a quaalude overdose in 1973.

"We called [quaaludes] 'the leg spreaders,' and I don't know if I want to get that crude, but that is what the whole point of them was," said Lisa Loving Barrett, Hefner's executive assistant from 1977–89. She added that doses of the sedative "were a necessary evil, if you will, to the partying."

Sondra Theodore was entrenched in that party lifestyle as Hefner's girlfriend from 1976–81, and she claimed that "Hef pretended he wasn't involved in any hard drug use at the mansion, but that was just a lie."

She recalled, "Quaaludes down the line were used for sex. Usually you just took a half. Now if you took two, you'd pass out. It was such a seduction, and the men knew this — that they could get girls to do just about anything they wanted if they gave them a quaalude." (Holly Madison, Hefner's girlfriend from 2001–08, corroborated that quaaludes were customary in Hefner's inner circle for decades.)

For the year up to Pollack's overdose, she "lived in the Playboy mansion pretty much from the get-go," according to sister Beverly Enright.

"It was hard, I think it was really tough. She didn't talk much about being a Bunny," she continued. "She did have some experiences — men would try to pull off the tail or try to be aggressive."

Still, says Enright, "I had no idea she was doing things like uppers or downers or anything else. I was surprised in a way, but I also knew her behavior had changed over the past year since she was in Playboy."

P.J. Masten, who worked in six Playboy Clubs across the country from 1972–82, said that when she transferred to the Chicago club, "a lot of Bunnies ... said Adrienne and Bobbie Arnstein supplied drugs for the Chicago mansion for parties for Hefner and his VIPs."

"I firmly believe quite a bit that she was involved with the drug trafficking," said Enright, pointing to a time when she found a dark wig that Pollack's boyfriend Jerry Pingitore claimed the blonde Bunny would wear while "trafficking" drugs. (Sister Laurie Donohoo also recounted a phone conversation when Pollack was in Miami with several other Playboy Bunnies and claimed she was with a "cartel member.")

So when Pollack overdosed just three weeks after her 23rd birthday in September 1973, investigators heightened their scrutiny of Hefner, who had already been in their sights for years.

Explained David Reuben, former Cook County State's Attorney investigator: "Law enforcement was looking at Playboy because they were the epitome of the deterioration of our culture — that was how they looked at it. And it was basically the start of the real War on Drugs, as they used to call it. People thought this was the den of evil, and they just thought Playboy needed to be shut down and squashed."

But, said Reuben, "We could not prove that the mansions had massive amounts of drugs or drug activity."

Inside the Mansions: 'A Pile of Cocaine,' Prescription Stockpiles and Hef's 'Puppets'

It seems the evidence was hiding in plain sight.

"There was drug use everywhere," said Theodore.

Masten, who dated Playboy's head of security, Joe Piastro, and was part of the company's unofficial "cleanup crew," described the scene: "At the time in L.A. when I was there, there were bowls of quaaludes, there were huge vials of cocaine."

Barrett affirmed, "Cocaine was a big deal. I can remember at a couple of the larger parties, there was a downstairs powder room off of the great hall that, underneath the ornate toilet paper holder, you would lift that up and there was a pile of cocaine under there."

Theodore even claimed that Louie, the dog of Hefner's close friend Joe Dante, "got hooked on cocaine. ... We had to lock that dog up when people were around because he was addicted to the cocaine and people you wouldn't even think were doing it were doing it." The tell? Louie loved licking party guests' noses.

As for the quaaludes, Barrett claimed Hefner deployed an extralegal workaround to ensure he a steady supply of the sedative.

"We would have prescriptions in some of our names," she explained. "There were prescriptions in Sondra's name and Hef's name and my name. ... We kept a desk calendar that would say 'Lisa's Q' or 'Hef's Q' or 'Sondra's Q' that enabled certainly four and sometimes five different prescriptions for the same medication to feed the machine. [All of those went] to Hef's bedroom, to his personal drawer — he had a drawer that none of us had access to, we gave them directly to Hef."

"Hefner was smart," said Reuben. "Was somebody going to come forward? No. Everybody wanted to be Hef's favorite, everybody wanted to be rising up in the organization."

But now, in Secrets of Playboy, someone finally has come forward: Sondra Theodore.

"I've never told anybody any of this before," she shared. "I was too ashamed for a lot of reasons, but I was a drug mule for Hef."

According to Theodore, she took her first "bump" of cocaine while living at the Playboy mansion. Then, once Hefner had sent her out on her first alleged drug run, "It was so easy for him, that became the norm. ... How many times did I pick up drugs for Hef? Uh, I don't know, countless, countless times. Oh yeah, I'd say once a week."

She continued, "Everybody did their own job, we all had to do exactly what he wanted, and we all did it like little puppets. If he gave you a job, it was almost an honor ... it's crazy, but it made me feel like I was important to him. When you think about, here's a man 30 years older than me and he's sending a young girl for illegal substances — it was nothing to him, it was like sending me out for a quart of milk."

Theodore knew that "if I got caught, my life would be over" — saying that the people who did get caught suffered for it — so her secret remained under lock and key for decades.

'They've Got Hefner's Right-Hand Gal'

And Bobbie Arnstein was perhaps the person who suffered most as a result of her proximity to Hefner as he clashed with law enforcement.

As Hefner's social secretary while he lived in Chicago, Arnstein was "a very big part of his life, she knew all his secrets," said Theodore.

Retired Chicago homicide detective Ted O'Connor recalled that the years when she was working with Hefner, "cocaine really exploded in the city of Chicago. It was everywhere. I heard the rumors that you could get whatever you wanted in the mansion," including illicit drugs. But given the cloistered atmosphere Hefner maintained, "somebody had to bring it in there" — and over time the question became whether Arnstein was trafficking drugs for Hefner.

Arnstein's close friend Keith Stroup, founder of the National Organization for the Reform of Marijuana Laws, did acknowledge that Arnstein was no stranger to drugs.

"One of Bobbie's jobs ... was that Hef insisted she always keep a box of hand-rolled [marijuana] joints on his bed stand in his private quarters," he said. "I saw occasionally amphetamines, but I never saw cocaine used in the mansion other than when Bobbie and I would occasionally snort a line of coke from a half a gram she had. But I will say this, we were very careful to keep it out of Hef's view or knowledge ... I was alerted that, 'If Hef or any of his people every see or hear cocaine, you'll never enter this building again.'"

Arnstein became "a target because of her association with Playboy and Hefner," and she also began to date a drug dealer. In 1974 she was arrested outside the Playboy mansion when a search of her purse turned up what Stroup calls "a small amount of cocaine." She was charged with conspiracy to distribute the drug.

"They brought her into federal court. Everybody thought, 'Whew, wow, the DA's really got whopper here — they've got Hefner's right-hand gal," said O'Connor.

Noted Stroup, "Any state in the country during those years, if you were busted with a half pound of cocaine, you're going to spend 10 to 20 years in prison. And she realized she was in a heap of trouble."

The trial began that July, and Arnstein and two other associates were convicted in October. The next month, she was sentenced to 15 years in prison.

"Within a few weeks, the government called Bobbie in to speak with them," said Arnstein's defense lawyer, now-Judge Joan B. Gottschall. "I remember being in a large room crowded with men, and Bobbie and I were there. And the government told her that they had information that there was a contract out on her life and that she needed to be 'very careful of friend and foe.' So I don't think for either of us there was any question of how we were supposed to interpret that odd message."

Stroup spelled out the veiled threat: "The only person that it made any sense to assume was that Hugh Hefner was willing to kill Bobbie Arnstein to keep the cocaine scandal out of his life and Playboy's life." But, he said, "that simply isn't believable for any of us who knew the two of them."

For his part, Hefner said in a news conference at the time that it was "transparently obvious" the government was pressuring Arnstein to flip on him and Playboy. He called it "arbitrary and capricious ... harassment."

And then investigators turned another screw, reopening the Adrienne Pollack case and subpoenaing Arnstein as a witness.

According to Stroup, "Bobbie had made it fairly clear to all her friends that she'd do whatever she needed to do not to go to prison, but she wasn't going to flip on Hef or anybody in the Playboy empire. So she took an overdose of pills, I think one or two in the morning, and took a taxi over to the Maryland hotel and got a room by herself, wrote her note out on the hotel stationery by hand, took her pills and went to sleep."

Bobbie Arnstein died on Jan. 13, 1975. Hefner served as a pallbearer at her funeral.

"The end was very scary," said Marilyn Cole Lownes, Playboy's 1973 Playmate of the Year. "She just couldn't cope, and she chose not to."

There was speculation that Bobbie had been murdered, but O'Connor's investigation (which was initially pursued as a homicide case) turned up no evidence to support that belief.

Her death was officially declared a suicide and without her testimony, the Pollack case was closed a few months later in the spring of 1975 — though Reuben said if people like Theodore had spoken up about Hef's drug use back in the '70s, "it would have changed the whole direction of the investigation ... and that would have left open the possibility of potential indictment of Hefner."

Stroup sees something more complex behind his friend's desperate end: "Bobbie was a feminist," he explained. "She wanted to be respected for her mind and for her achievements and for her judgment. On the other hand, she put herself into a world where every woman was a sex object."

He continued, "I think it was the conflict at the center of Bobbie's soul. Bobbie clearly understood that this world that she lived and thrived in ... was also based on exploiting other women. It must have caused some guilt."

Still, Theodore hopes justice can now be found for Arnstein and Pollack and so many more women who found themselves in service of Hefner over the years.

"To put a young girl in that position was so dangerous," she said. "I didn't allow myself to know that that was abusive because I was told that it was in love, in the name of love."

She said that if Hefner, who died in 2017, were alive today, "he would be in jail. And wherever he is — and I don't think it's a good place — I know he knows that I've told the truth."

Playboy issued a statement shortly before the A&E docuseries' premiere on Jan. 24 that said, in part, "we trust and validate women and their stories, and we strongly support the individuals who have come forward to share their experiences."

They added, "Today's Playboy is not Hugh Hefner's Playboy."

Secrets of Playboy airs Mondays at 9 p.m. ET on A&E.

If you or someone you know is struggling with addiction, please contact the SAMHSA substance abuse helpline at 1-800-662-HELP.