At the age of 91, pornography’s pioneer and first gentleman has passed away.

Hugh Hefner leaves behind quite a legacy. It’s fitting that he’ll soon be buried right next to Marilyn Monroe, in a Los Angeles crypt he purchased years ago, since it was her photograph that graced the very first cover of Playboy Magazine.

The year was 1953, and Hugh had borrowed some money (some of which was from, funnily enough, his own mother) to develop a publication that would, eventually, explode into an empire. He’d previously been employed by a children’s magazine, was a new father, and had decided it was time for a change. Although Playboy is best known for its pornographic centerfolds, from its inception the magazine also featured articles by authors ranging from John Updike to James Baldwin, and interviews with the likes of Bette Davis and Martin Luther King, Jr. Conversations about politics, social issues, entertainment and race dominated the pages. (This may serve to explain part of the reason why some claimed they read it “for the articles.” Although I admit I don’t believe it for a minute.)

Hefner’s bold new concept was reflected in a magazine ultimately dedicated to a combination of high culture and progressive sexuality. It catered to a particular sort of man and was, according to a sociologist quoted recently in the New York Times, “part of an ensemble with the James Bond movies, John F. Kennedy, swinging, the guy who is young, vigorous, indifferent to the bonds of social responsibility.”

Nothing, it seemed, was too much or off limits for Playboy.

Before long, it was the most popular men’s magazine in the world. The brand spawned a clothing line and a number of resorts and casinos, along with a television network. The centerfolds themselves may have begun to look downright tame compared to what other pornographers were now publishing, but it hardly mattered. Mr. Hefner had built a kingdom and he was, by all accounts, the reigning king.

He was also, it turned out, a social activist with an agenda.

While the man in the satin pajamas has become an American caricature—the sleazy producer of explicit content, living in an opulent mansion and surrounded by women not even half his age—his cultural influence when it comes to sex should not be underestimated. For while he may have been a product of the sexual revolution, he was also a catalyst—arguably, one of the biggest and most effective. Otherwise good (albeit naive, at best) American men and women were ready, I suppose, for someone to come along and put a pretty face (or body) on the revolution. Hugh got all the credit (and, thanks to his business acumen, the payoff), but he also needed willing participants. A captive audience. He and his obscene magazine did not skyrocket to fame in a vacuum. The truth was that he wasn’t just selling pornography—he was selling the whole package, a supposedly sophisticated and enlightened manhood marked by the aforementioned “indifference to social responsibility.”

This philosophy of the human person necessarily included the throwing off of religious mores, the embracing of birth control, and the acceptance of abortion. Ten years before Roe v. Wade, for example, Playboy was publishing no small number of pro-abortion articles. The separation of church and state, and the oppression of women by religious communities (oh, the irony), were also issues important to Hefner. As to his apparent obsession with sexuality, it may surprise some to know that the founder of Playboy was a virgin until shortly before he married his first wife, at the age of 22. But not long after marrying, the story goes, Hugh’s new bride confessed that she had cheated on him prior to their wedding. Within four years, Playboy was born, and some have speculated that this painful betrayal played no small role in Hefner’s adopting and promoting such a sexually “liberated” lifestyle. Discovering that he had been duped, that his wife was more sexually experienced than he, was difficult to take.

Regardless what the impetus was, the sad result remains the same. Men, casually flipping through the glossy pages, came to see themselves as connoisseurs of women. Chastity gave way to pornography addiction, which was fast becoming normalized and a mark of true manhood. Lost was the sense of duty, that chivalrous masculinity rooted in virtue and self-discipline. But it wasn’t just the men throwing off the shackles of convention, and  following the Hefner Way. In spite of being objectified and debased in every single issue of Hugh’s magazine, the daughters of the sexual revolution began to abandon home and hearth for the promises of career, the attentions of men, and what they saw as the benefits of a “free” sexuality. Contraception was, of course, essential. The ensuing legalization of abortion, 100 percent necessary. Soon, divorce was no big deal. Nothing was truly impermissible, and everything was allowed in this new lifestyle—provided that it did not restrict or impinge on the ever-expanding definition of what constitutes a healthy human sexuality. It should come as no surprise that in his later years, Hugh Hefner championed same sex marriage.

Although he is gone now, the principles and values on which Hugh Hefner built his empire will, unfortunately, live on into the future. And while he was instrumental in doing much of the planting, the truth is that the sexual revolution had already begun to produce a culture of fertile soil, ready and waiting to be cultivated and watered. Like Margaret Sanger, Betty Friedan and Alfred Kinsey, Hefner envisioned a world where liberated men and women might create their own respective destinies—where religion, a traditional understanding of moral decency, and the complementarity between husband and wife are no longer relevant. He and his cohorts, separated only by time and place, together ushered in an era of deconstruction and, later, confusion. Dissatisfied with the standard answer to the question of what it means to be a man or a woman, Hefner simply took to his pen. And found a way to revolutionize society.

Hugh Hefner was a problem, but he was certainly not the only problem. When his publication first arrived on the scene people, either hungry for something new or simply not strong enough to resist, ate it up. They bought his magazine and, right along with it, his coming-of-age philosophy. The culture changed. Dramatically. Suddenly pornography had been enshrined as a sort of national past time, destroying who knows how many marriages and crushing untold numbers of souls. How many young boys lost some measure of their innocence when they happened upon Hugh’s latest issue? Ideally, people would have seen the Playboy franchise for what it was: yet another iteration of the new world order, hell-bent (literally) on tearing apart the very fabric of society. If only they could have understood that the image of the successful, happy, martini-guzzling gentleman portrayed by the magazine was just a mirage leading to nowhere, and that true happiness can only come from living up to one’s human dignity. If only they would have chosen better things instead, like chastity and love and life. If only men had taken their social cues from Hefner’s contemporary, the Venerable Bishop Fulton Sheen, who once said “Show me your hands. Do they have scars from giving? Show me your feet. Are they wounded in service? Show me your heart. Have you left a place for divine love?”

Pandora’s box is, effectively, open. We can never really go back to before the sexual revolution, before legalized abortion and the birth control pill and widespread pornography addiction. But when we consider the sad legacy of Hugh Hefner and his work, we see clearer than ever that his empire was mere make-believe. It was built on nothing but a crumbling, desperate and vile house of cards.