Hugh Hefner’s Twisted Vision of Freedom

Without the money and fame, Hugh Hefner would have been called a common pimp, scumbag, and drug addict.

A&E’s Hugh Hefner documentary, Secrets of Playboy, a 10-part series releasing episodes on Monday nights, is more than the pop-culture debauchery it describes. It is a deep lesson on the destruction one life can cause when it seeks a false vision of freedom. 

Hefner considered himself “a very moral guy” and, above all, “a playboy philosopher.” All his actions were seemingly justified as a way to defeat the religious “repression” of his Methodist parents and of American culture in general, aiming to replace it with complete freedom. But each episode shows just how twisted Hefner’s kingdom of self-gratification became, as insiders reveal all the lives ruined through drug overdoses, suicides, sexual exploitation and excess. 

One longtime girlfriend, Sondra Theodore, who dated Hefner for five years in the ’70s and early ’80s, said, “I watched girl after girl show up, fresh faced, adorable and their beauty just washed away. We were nothing to him. He was like a vampire. He sucked the life out of these girls for decades.”

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His closest confidants say he was so focused on enjoying every moment to the absolute fullest that he ate two to three pounds of M&Ms a day, drank 40 Pepsis a day, and spent many hours playing games in his arcade room or by the pool—like a child who refused to grow up. 

In an interview with the Los Angeles Times in 1992, Hefner said, “Much of my life has been like an adolescent dream of an adult life. If you were still a boy, in almost a Peter Pan kind of way, and could have just the perfect life that you wanted to have, that’s the life I invented for myself.” 

But it was not just innocent childhood fantasies that Hef wanted to live out. The documentary quotes a number of his employees as saying he required them to have prescriptions to quaaludes, a strong barbiturate often called “the date rape drug” but which Hefner called “leg spreaders.” He would then take his employees’ prescriptions and put the bottles in a drawer in his bedroom, where he also kept mounds of cocaine, amphetamines, and marijuana. 

Employees report that Bill Cosby, who is also accused of using quaaludes to lower women’s inhibitions for sex, was regularly present at the mansion, as was statutory rapist Roman Polanski. One 15-year-old girl claims Cosby raped her using quaaludes while at the Playboy Mansion. P.J. Masten, a former Playboy bunny, told CNN that she personally knows at least 12 other bunnies, in addition to herself, who were drugged and raped by Cosby. But she says people didn’t say anything because Cosby was known as Hefner’s “best friend.”

The documentary describes at least one incident of Hefner attempting to sleep with an underage girl, as well. The interview with his former doctor’s daughter reveals that he allegedly invited her (unsuccessfully) into an orgy when she was 17. 

While these accusations of using date-rape drugs to entice the young, aspiring models to sleep with him date back to the early days of Playboy, recent “girlfriends” of Hefner reported similar experiences. Holly Madison, of “Girls Next Door” fame, said in her book that Hefner offered her quaaludes before they had sex for the first time. In the Sunday Mirror, twin sisters Karissa and Kristina Shannon said the first time they had sex with Hefner, at 19 years old, “He told us the drugs would help with our anxiety.” Then he gave them quaaludes, which made them feel “loose and fuzzy,” before having them “summoned to his bedroom.”

After it was over, they said, “It was creepy and gross. We felt filthy, disgusted, like our bodies weren’t ours…It was almost 5 a.m. when we got back to our room that first night and we agreed, ‘He is the devil. He has a black soul. He is going to hell.’” This comment about Hefner being the devil was repeated by another playmate who, when she committed suicide, was found with the message “Hugh Hefner is the devil” in big letters on the wall. 

Now that he’s passed, the twins said that even though they had “dated” Hef for two years in the early 2010s, they were glad he was now dead so other girls would be spared their experience.

Hef acted like he owned you. If we broke his rules, six guards would drag us to our room and not let us leave. Hef called it “HMH arrest,” after his initials. He preyed on vulnerable young girls like us. He would offer you the world, then keep you trapped in his house, which was like a golden prison. When Hef died, part of us did feel sad, but another part was like, “OK good, no more girls are going to be groomed and ruined like we were.” 

Without the money and fame, Hefner would have been called a common pimp, scumbag, and drug addict. Instead, he lived as a celebrated cultural icon until his death at the ripe old age of 91—the guy who made pornography classy and sophisticated. 

But maybe the most interesting thing about Hugh Hefner is the fact that he thought deeply about what he believed, and all he did was in accordance with those beliefs. Above all, he believed in “freedom,” by which he meant complete individual autonomy. People couldn’t tell him what to do—whether that was eating (literal) pounds of M&Ms, having a dozen girlfriends at a time, snorting cocaine in his pajamas until 6 a.m., or anything else.

His political activism for sexual liberation and drug legalization was based on this same flawed view of freedom. While he received awards for championing freedom of speech (i.e., pornography), at the same time he was also silencing journalists, whistleblowers, and former employees. The documentary shows how Hefner had cameras recording in every corner of the house, the pool, and even behind bushes in order to catch journalists, and other people who might decide to turn on him later, doing things they wouldn’t want released to the public. So much for freedom of speech or the press. This was also allegedly a tactic of another serial abuser of young women—Jeffrey Epstein. 

But the irony of this freedom-as-autonomy model is that if you get everything your desires crave at every given moment, you end up making a slave of not only everyone around you, but your own will. Hefner’s household help said he told them they were not to make conversation with him, look him in the eye, or expect him to ever learn their names. Like the young girls, they were a means to an end.

Hefner once said, “One of the great ironies in our society is that we celebrate freedom and then limit the parts of life where we should be most free,” by which he meant sex and expressing oneself. He also said, “If a man has a right to find God in his own way, he has a right to go to the Devil in his own way also.” 

But in the Christian tradition, freedom is not the ability to choose whatever good or evil you desire; it is the ability to choose the good. This may sound like a contradiction, or like God is saying, “You’re free to do what I tell you to do.” But if you are created by an intelligent being for a purpose, then fulfilling that purpose without being impeded by bad ideas, outside forces, or uncontrollable inner urges is freedom. 

A boat created to float down the river is not free if rocks obstruct its way or the river runs dry. It is free when it accomplishes its telos, traveling unencumbered. If the boat were conscious and it tried to leave the river and travel by land, we could only assume its true purpose was no longer clear or accessible to it. 

In the same way, if you immediately give in to every urge simply because it’s there, and then become addicted to the satiation of those urges, you are no longer free. You’ve pursued something that is opposed to your purpose—since momentary pleasure is not your telos—and are now impeded in living as your true self. 

Considering someone like Hugh Hefner free, as he humps a dog while finishing his 40th Pepsi and 20th line of coke for the day, is obviously an illusion. His body may have been free in its ability to pursue the desires of his will, but his will was captive. He was a slave. And like anyone whose will is enslaved, whether an opioid addict or someone who can’t stop playing video games until 3 a.m. every night, he undoubtedly sensed his lack of control, his lack of real freedom. 

The description of him as a vampire is fitting, as he needed to suck the goodness he experienced in life from other people. His soul—separated from God—no longer had much to tap. I can think of no better image of these two conflicting visions of freedom than Jeremiah 17:5-8: 

            Thus says the LORD:

            “Cursed is the one who trusts in human beings,
                        who seeks his strength in flesh,
                        whose heart turns away from the LORD.
            He is like a barren bush in the desert
                        that enjoys no change of season,
            but stands in a lava waste,
                        a salt and empty earth.
            Blessed is the one who trusts in the LORD,
                        whose hope is the LORD.
            He is like a tree planted beside the waters
                        that stretches out its roots to the stream:
            it fears not the heat when it comes;
                        its leaves stay green;
            in the year of drought it shows no distress,
                        but still bears fruit.”

Created to find our life in Him, we are like a tree by a river when we trust in the Lord; but we are like a barren bush in the desert if we seek our strength apart from Him. This barren bush might have the illusion of freedom—if it chose that spot in the desert. It also may experience a level of flourishing—if it manages to suck the life from all the other lifeforms around it, like Hefner did. But true freedom and flourishing exist in finding our purpose in loving God and neighbor, planting ourselves by the river of life. 

[Photo Credit: Robyn Beck/AFP via Getty Images]


  • David Larson

    David Larson is a writer and editor whose work has appeared in the Federalist, Crisis Magazine, Front Porch Republic, and Catholic World Report. He has a masters in theological studies and is currently opinion editor for Carolina Journal in North Carolina, where he lives with his wife and family. David can be reached here.

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