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Why Anna Wintour Is (Still) One of Condé Nast’s Most Powerful Assets

The company's artistic director and editor of American Vogue has extraordinary power and influence. What happens when she eventually steps down?
Anna Wintour | Photo: Patrick Demarchelier
  • Amy Odell

NEW YORK, United States — At Condé Nast's NewFront presentation in April, Anna Wintour performed a bit of theatre. She sat onstage behind a desk, in a set made to look like her office, and fielded pre-planned questions from the audience, in a live version of her famous YouTube series, "Go Ask Anna," where the general public get to lob her banal questions ("Do you believe in a signature uniform?") in pre-recorded videos. The series was a highlight of the annual showcase, in which media companies attempt to attract ad buyers to their internet videos via celebrity performers and gimmicky snack food, showing that her power continues to take on new and necessary shapes, filling whatever revenue void Condé Nast needs her to fill.

That she can even pull off such a series speaks to her fame and extraordinary cultural influence. What other magazine editor would draw hundreds of thousands of views by sitting in her office and talking to camera? What other magazine editor with the level of celebrity and responsibility that Wintour has, as editor-in-chief of American Vogue and artistic director of all of Condé's titles, would even bother spending time on the minutia of content creation?

The series is just one of the more recent examples of both Wintour's work ethic, which those who have worked with her describe as remarkable, and her evolving influence in a media industry that demands more of its talent than ever before as financial returns continue to diminish. Though Condé Nast has suffered significant financial losses in recent years, the expense of keeping Wintour on the payroll — probably at least a few million dollars a year — is likely more than worth it for what she brings to the company. Hearst may be embracing the end of the age of the "cult of personality" editor, but Wintour gives Condé Nast a reason to keep it alive.

Wintour started as editor-in-chief of Vogue in 1988 and likes to tell the story of how her first cover was such a radical departure from those of her predecessor, Grace Mirabella, that the printers called to make sure there wasn't a mistake. Mirabella ironed out a successful formula and stuck to it month after month, which tripled Vogue's circulation over her 17-year tenure. But her covers were perhaps too predictably a headshot of a model with perfect hair and perfect blush, and S.I. Newhouse wanted a change of direction to keep the magazine competitive with Elle. Wintour's first cover was a model wearing a $10,000 Christian Lacroix sweater and a $50 pair of Guess jeans, walking outside with undone hair and a toothy grin — an image you could easily imagine appearing in a street style slideshow today. Though the idea of mixing designer pieces with mall brands has become rote, it was incredibly surprising at the time.

Wintour's influence would only grow from there. She was early to see the link between fashion and celebrity culture, and started putting celebrities on Vogue covers, famously featuring Madonna in 1989. Though celebrities would become the de facto faces of magazine covers, Wintour was instrumental in building and exploiting the celebrity-fashion industrial complex that, at the time, wasn't nearly as obvious as it is today, when many people outside the fashion and entertainment industries understand that celebrities borrow dresses to wear to the Oscars, and the dresses they wear may stem from endorsement deals or other forms of payment.

By 1997, nearly 10 years into her editorship, Vogue's then-publisher Ronald Galotti was boasting to the New York Times about that year tracking to deliver the best financial results in the magazine's history. Designers wanted to appear in Vogue and to receive the magazine's endorsement, and Wintour admitted that she favoured advertisers when deciding which labels to feature in the magazine (though she also promoted Marc Jacobs, who had no advertising budget then). It meant something in the fashion industry to have her approval and access to her or her team of editors (look at Jacobs now), many of whom became powerhouses in their own right, and brands were willing to put advertising dollars toward that access.

Today, of course, a print magazine — even Vogue — doesn't carry the same weight as it did in the late '90s or early 2000s, which is when Condé Nast launched its first websites. Executives at the company didn't understand how significant digital media would become and allowed the sites to be used merely to boost print revenue and circulation, rather than forcing their star editors, including Wintour, to turn them into their own thriving editorial destinations and businesses.

Wintour is a perfectionist, but her tenure hasn't been perfect.

This attitude, that the internet could be brushed off and not minded with the same level of attention given to print media, would become one of the company's biggest problems. Though Wintour takes the blame for this and the company's other failings as its most public face, this miscalculation wasn't hers alone. She may have been slower to throw her weight behind Vogue's digital presence than other visionary editors at other media companies, but by 2013, according to a Harvard Business Review case study, she was meeting every Tuesday with the web team to approve lineups, and devoting time each night to looking at the site, just as she famously does with the magazine. And besides, even the magazines that were early adopters of the internet face the same major problem: Facebook and Google dominate the market for digital ad dollars.

Wintour is a perfectionist, but her tenure hasn't been perfect. Many wondered, after longstanding Vogue photographers like Mario Testino and Patrick Demarchelier were outed in the #MeToo movement — following the momentous downfall of her friend, Harvey Weinstein — why Wintour didn't do anything about this disturbing behaviour, proactively shielding vulnerable models, in the industry synonymous with her name, from sexual predators. (Following a major New York Times exposé, Condé Nast implemented a "code of conduct," with Wintour's support, designed to better protect models on its shoots.) What's more, her efforts as artistic director to bring a Vogue-like aesthetic to other Condé Nast titles, like Self, which shuttered its print edition, didn't end up working particularly well.

Then, there are the controversies over coverage that Vogue has faced every so often, including the outrage over its flattering 2011 profile of Syrian first lady Asma al-Assad and its more recent suggestion that Cara Delevigne's sexuality is a phase. But none of the dustups have sent advertisers fleeing. Vogue is even said to have weathered the exodus of print advertisers that contributed to Condé's reported $150 million in losses in 2017 much better than many of the company's other fashion titles. And as magazines scramble for alternate revenue streams, Wintour's Met Gala has become the most powerful and visible part of the Vogue brand, a spectacular intersection of the entertainment and fashion industries that Wintour has nurtured for decades. Though the money raised from the gala benefits the Metropolitan Museum's Costume Institute, celebrities and designers vie for invites, which are managed personally by Wintour, and the content Vogue publishes from the event is likely among its most lucrative.

What happens to Condé Nast when Anna Wintour finally steps down?

Rumours of Wintour's departure have circulated for years, reaching a crescendo last spring, when The New York Times published a 2,000-word piece entitled "Imagining a World After Anna." But one thing is for sure: her exit, whenever it comes, is inevitable.

Post-Wintour, the Met Gala will also lose its chief planner and, likely, some of its relevance.

Wintour's departure will leave many voids at Condé Nast. Most significant of all will be the void left by her power-influencer status, and the ability she has to make fashion brands and other fashion and entertainment industry figures feel the need to be involved in what she and Vogue are doing. Post-Wintour, the Met Gala will also lose its chief planner and, likely, some of its relevance.

So, while it might seem crazy for a company like Condé Nast to pay her millions of dollars in salary along with her clothing allowance and other expenses, it would probably be crazier for them to let her leave, and let all the value she continues to create for the company follow.

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Inside the $7 Billion Dior Phenomenon