Mr. San Miguel is spot on (as the Brits are wont to say). The Playboy brand simply didn't have legs. Or, more precisely, it refused to spread its legs.
Ironically, Heffner's prurience was his undoing. If Playboy had planted an upmarket flag in the hardcore video industry when the biz exploded (so to speak), it may have been able to carve a small but profitable slice of the porn pie. But Hugh couldn't reconcile "the Playboy man" and actual, honest-to-God sex. The author's analysis of Playboy as nudity purveyor is just so. Playboy died for the non-sins of Heff's retarded schoolboy sexuality.
That said, video technology and the internet eliminated the porn industry's barrier to entry (what is it with these double entendres?). Volume skyrocketed and margins collapsed.
Could Playboy-branded upmarket porn have survived the Internet deluge? The fact that upmarket sex videos are conspicuous by their absence suggests that the niche was/is too small to offer Playboy a profitable place to shelter.
Also, Mr. San Miguel is right about Playboy becoming a joke. Which is a shame. Like all businesses, the sex industry has a high end (quality, price no object). I'm not sure how that could have been [legally] monetized by the Playboy brand. But one thing's for sure: Hugh Heffner was NOT the man to do it.
The deal to sell Playboy doesn't include editorial control. Which means Hugh is still perpetuating his Barbie ideal. Which is a shame.
There's only way for Playboy to survive. Hugh Heffner to step aside or, let's face it, die. Only Hugh's extraction from the biz could give it the breathing space it needs for someone with a genius for the sex biz to reinvent and reinvigorate the company. As what? F knows.
Meanwhile, I disagree with Mr. San Miguel's contention that Playboy can make any money from its intellectual legacy. I can read an interview with Norman Mailer---or his latter-day equivalent---for free from any number of websites. Speaking of Austin Powers, "I read Playboy for the articles" lost its potency, what, forty years ago?
Bottom line: the Playboy brand wasn't strong enough to go the distance.
At least not without changing its definition of "clean". That was always its basic problem. As a time when even the Kinsey report was saying that "normal people" all have some damn crazy things they like, his vision of "clean" didn't even included actual sex, never mind fairly normal sex, like lesbianism, which has always been more accepted than almost any other type, including even straight, for some guys who wanted to see sex, but not get caught seeing "sex".
His clean is the called "boring" to 90% of the people in the world, and that was, quite frankly, true even "before" the internet. He also got competition, first via Hustler, which became the instant anti-Playboy among all the people that hated nudity entirely, but at least wanted it "clean", followed by probably a dozen others. No one cares about seeing someone naked any more, unless they are 14 and stealing the porn from under dad's mattress. You can find nude by bloody accident, and, in some places, you don't even need internet access, just a neighbor that doesn't give a shit about the social norms some people had "in" the 60s, when "normal" people didn't sun bath without clothes on. If you do have the internet... You don't even need to go to sites involving sex at all, you can bloody find nude, with the "safe" non-sexy poses he promoted, on bloody nudist websites, where they don't even want people looking to sexual imagery.
Get that.. You can go to sites dedicated to people just taking pictures of their every day lives, who don't intend to sell sex, and find stuff. How do you compete with that, if your premise is, "Natural, not explicitly sexual, images of nude people."? You don't. The people that want, or care, about such stuff also don't want to admit they buy it, because they are the sort that would call **anything** even mildly more erotic "trash". The Overton Window has shifted, and was already in motion when he first published. The closest thing to a clue he ever had was the "Playboy channel" for TV, which had actual sex on it, and even that has been overtaken, by of all things, Showtime and the like showing much crappier "soft porn" after 1AM. A channel you can get as part of a package deal, without having to *ask* about it, because the other ones, like Playboy, are never listed in the "official" pamphlets given out to the general public.
Kind of ironic. The TV channel, if it still exists, is "too racy" to be listed, but the magazine, which tries to avoid racy like the plague is going under... Its absurd.
But, to answer the question, the sort of man that read it grew up, realized that normal people don't obsess over nudity for its own sake, and came to realize that the whole spectrum of things contains stuff from the, "normal, but Playboy will never show it", to, "Eeegads! They do that crazy shit in Japan?!", which you have to practically smuggle into the US. In short, Playboy is what you hang on the wall, next to the poster of Optimus Prime, not the stuff you hide under the bed any more, unless you are still living in some of those places where 90% of the population buys it, and 80% of the population demands the government stop people from selling it, because its *evil*. lol