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Michael Wolff on Trump, Cosby, Caitlyn and the New Gossip Culture

As 'Page Six' goes, so goes the nation: Gossip, the once-small Hollywood sideshow, now has major news status and defines the fate and fortunes of major public figures.

There is hardly a better example of the power and value of the New York Post‘s “Page Six” than Donald Trump. Despite Rupert Murdoch‘s recent tweets against him, Trump is a Murdoch gossip creation. Near-constant coverage during the 1980s and ‘90s of his marriages, his posturing and his bling, together with Trump’s own deep and prescient understanding that publicity is a golden currency — hence his ardent cultivation of the Post and “Page Six” — turned him from middling real estate developer into personal brand, national figure, reality show star and now, extraordinarily, frontrunner Republican presidential candidate.

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Quite the extraordinary realization is that a generation or two ago, most news was event- and institution-driven, with the personalities involved, bystanders and great men alike, treated in formal and remote fashion — apparently still the retro expectation of most politicians: ever dull, impersonal and stiff.

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Nothing so much has changed journalism, the entertainment industry and the greater public discussion as the personalization of news, that decadeslong trend that has exponentially increased in fervor in the digital age and has its apotheosis in Trump.

Gossip, once a small-time Hollywood side-show, now has major-news status, with the fate and fortune of public figures — and not a few private ones — a reflection of how well they play and court the gossip and personality press or how roused and angry it gets in pursuit of them.

The Cosby Corollary: When the star’s alleged sexual assaults were elevated from rumor to news, more women felt empowered to come forward.

Trump might just as logically have been a subject of media scorn and scandal — indeed, the large field of his political opponents seems wholly confounded that he is not — rather than a figure of epochal excitement and importance (at least in his and the media’s view). Likewise, Caitlyn Jenner might as easily have been a story about shame and reproach, a deer in the headlights pursued by the paparazzi, rather than someone of near-historic stature — an outcome that arguably is less about changing times than about a practiced and cunning handling of the gossip press.

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On the other side, Bill Cosby‘s accusers, who in the past might not have had a voice in the celebrity-dominated press and whose claims were all but ignored for a decade or more, now fuel its inverse reflex: to expose and dismantle the pretenses and con jobs of the rich and famous.

Gawker‘s reporting on plans for a gay tryst by a married publishing executive without public profile or significance, a kind of moral vigilantism, was met by a level of opprobrium and revulsion that might seem to draw a line in the sand about the ever-greater gossipification of news and culture. But, as likely, it merely suggests that the subtleties and high politics of the gossip world — stretching from “Page Six” through to Gawker, with celebrity magazines, tabloid TV-news shows, paparazzi sites like TMZ, reality stars like the Kardashians and sex tapes in between — can elude practitioners, as well as subjects. For all involved, it’s a high-wire act, not least of all because so much is so nakedly at stake.

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Gossip columns always have been a journalism power center, allowing a spin that operated outside of conventional reporting standards, uniquely susceptible to entreaties and deals and suited to no-fingerprint knifings.

Murdoch has accepted the New York Post‘s losses, reaching as high as $100 million a year, largely because of the clout of its gossip franchise. “Page Six” became the official tool of Murdoch favor and hazing, the way to reward his friends and to punish his enemies.

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At the same time, outsiders also could play the “Page Six” game. You could hardly function in the PR business representing any aspect of the news, music, sports or entertainment industries or any enterprise related to those businesses (fashion, restaurants, publishing) without having a relationship with “Page Six” — and trading favors for plugs and protection. PR man Howard Rubenstein, who counts both Trump and the Post among his clients, made himself into a central New York power broker because of his relationship with “Page Six.” The Post and “Page Six” became a tip sheet for the rest of the tabloid-news and entertainment-media complex, supplying the ever-more-popular gossip narrative — Trump’s one of the foremost among them.

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But then, with the rise of the Internet, gossip came under a seemingly dramatic revision. It went from a game for insiders to a game of outsiders. Nick Denton‘s Gawker, with its Robin Hood mission, was out to take glory and satisfaction from the successful and celebrated and spread Schadenfreude among an outsider class. (Murdoch himself in 2007 joked that he had to buy The Wall Street Journal to stay ahead of Gawker — although he called it “Stalker.”)

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What heretofore was gossip — even at “Page Six,” they still were unabashedly gossip columnists — became at Gawker something of a political act. Gawker explicitly made the connection between its coverage and what it saw as the hypocrisy and iniquity of the new ruling class. Success itself became a reason to target you. Gossip was an activist’s new weapon.

“Page Six” Paterfamilias: Murdoch’s New York Post was the early frontier of the gossip revolution.

Gawker and its staff of young writers, few who had professional experience beyond Gawker itself, came to believe that their trade was a kind of muckraking journalism — a truth mission, even. What might seem like mere gossip really was the thread of a greater conspiracy, with sex the ultimate symbol of the patriarchal plot. In a kind of left-wing moralism combining feminism and economic populism (though gossip in Murdoch’s world — and, before that, in the Hearst-dominated gossip press — largely was a right-wing conceit, the Internet took it left), tinged with a Lord of the Flies kind of empowerment, anything but the most conventional sexual behavior on the part of successful men was exploitation and depravity worth exposing.

Indeed, the willingness of the news media, particularly the Internet news media, to print the heretofore unprintable changed the tenor and method of public combat: Allegations in legal filings, no matter how unsubstantiated, can instantly become significant news. Accusations are real. (All enterprising news organizations now have reporters dedicated to combing court filings precisely for these sorts of vivid — all the more vivid because they are one-sided — personal attacks.) And nobody is gossip-proof.

Yet while gossip is a game of manipulations and hucksterism, payoffs and paybacks, political alliances and pure pugilism — e.g., Trump’s indefatigable threats, lawsuits, insults and bullying — that vastly undermines any idea of objective news coverage, it is strangely uncontrollable too, inventing its own peculiar moral framework.

At its heart, and at its most riveting, gossip bridges the space between public illusion and private reality; its news value, and frisson, is in the deconstruction of hypocrisy, targeting the sweet spot in public consciousness — that widespread belief that the real story is never told, that no one is who they say they are (unless, of course, like Trump and the retinue of reality stars, you stand proud and naked, ridiculous and moronic, before the gossip press).

Curiously, Gawker, in its attack on the hapless publishing executive, found itself on the wrong side of gossip’s moral equation. It was Gawker that now seemed to have the opaque agenda and unctuous morals, its own purity undercut by its fetishistic interests. It was not even so much that the site had harmed an innocent person, but that it seemed weird and creepy about it. Gawker was the pervy party, suddenly caught in the headlights. Or, put another way, Gawker committed the ultimate gossiper’s sin: It took itself too seriously. That’s the quicksilver attribute of the gossip media and the ideal gossip personality: never for it to be entirely clear if you are in earnest or just kidding. That’s ultimate deniability.

Such a sleight of hand and fine tonal calibration make everybody else look suspect and insincere, the pained condition of most modern politicians. Hence, the once and future Trump — with always a next chapter, perhaps the longest running tale in modern gossip history. (Gawker, whose very mission is to bring down someone like Trump, has not been able to touch him, feebly trying to ding him by publishing his phone number, a tactic borrowed from Trump himself.) Laughing with him merges with laughing at him, which, in some ultimate defense against political and media rectitude, aligns his personality with every expectation.