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Good evening, I’m Dylan Byers. Welcome back to In The Room, my biweekly private email on the media industry.
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In The Room

Good evening, I’m Dylan Byers. Welcome back to In The Room, my biweekly private email on the media industry. Tonight, we go inside the Vogue empire, where Dame Anna Wintour is discreetly trying to manage the meteoric rise of Edward Enninful, the visionary editor of British Vogue. As their long frosty relationship spills into public view, the two met in Paris today—to talk business, yes, but also to delicately hash out grievances.

The Treaty of Paris
The Treaty of Paris
What to do when a living legend wants to keep working while her true natural heir is a future legend sowing his oats, and eager to expand his footprint? And when there is some history between the two, and the future of a historic brand hangs in the balance? Only at Condé Nast…
DYLAN BYERS DYLAN BYERS
Condé Nast was never the largest media player in New York, not by a longshot. But the Newhouse family’s privately held magazine kingdom was always the most fabulous, the most glamorous, and certainly the most decadent—the rows of towncars outside 350 Madison and then 4 Times Square; the extravagant office flowers flown in from Amsterdam for the biggest events; the privately financed apartment-or-townhouse deals for top creative and financial executives who had to embody the lives they portrayed; the corporate retreats in Milan, taking over Hotel Cipriani in Venice; those leaked Four Seasons holiday luncheon seating charts, where an editor’s proximity to Si Newhouse projected their status; well… those were the days.

Back then, of course, Condé’s operations were inextricably entangled with the company’s unique confection of court politics and creative intrigue. Si, after all, was minutely involved with the various fiefdoms inside his business. He routinely presided over the “print order” meetings in which each title’s editor-in-chief and publisher would present the “book”—then an analog album of manually-inserted advertising and editorial pages—to an assembly of executives. And despite his enormous fortune and vast media holdings, he lunched monthly in the cafeteria (where garlic, to which he had a material distaste, was verboten) with his top editors at the booth behind the checkout station.

In those days, the company made billions off of the creative genius of its top editors and their rapacious publishers, much of which was reinvested into the product. Expenses were rarely spared: covers in exotic locations would be reshot if Annie Leibovitz couldn’t accomplish her best work; writers flew business and were holed up in expensive hotels on deadline. (Multiple memoirs have portrayed this culture.) Page Six and Women’s Wear Daily often feasted on Condé Nast for the obvious reasons: it was a creative company run by creative people, administered by Si, himself a true patron of the craft, who seemingly loved his magazines as much as the priceless art that he collected. And it was also a sharp-elbowed place where editors jostled with their peers at other publications even though all the checks came from the same place. Assistants and junior editors were politely told never to talk business in the elevators since that’s where their competitors were, too.

The Wintour of Solidarity
Culturally, of course, this all began to change as the magazine industry’s fortunes began to fade—post-Google and Facebook, post-2008, post-iPhone and the misguided pivot-to-video. The go-go ‘90s were followed by the afterglow of the aughts, which was followed by the corrective teens when management encouraged, and then insisted, that rival publications work together so that redundancies could be eliminated in order to operate the business more efficiently. And in many ways, the later-in-life solidarity was championed, at least on the editorial side, by Anna Wintour, the legendary editor of Vogue, genius behind the Met Ball, roman à clef heroine of The Devil Wears Prada, and reluctant star of The September Issue. In 2013, she was elevated by the Newhouses and then-C.E.O. Chuck Townsend to the title of artistic director, which reflected her status as the editor of editors. Other legends in the building, like Graydon Carter and David Remnick, maintained their direct connections to the family and exalted status, but Wintour was otherwise in charge of the rest of the lot.

From the start, she surprised many with her commitment to rolling up sleeves, encouraging communication across departments and titles, and embracing the new world. This was Condé Nast, and yet it was also the new Condé Nast, a matrixed organization where P.R., design, and research teams were being centralized; print products were being closed; and legends were leaving the company and the industry altogether. Many wondered aloud why Wintour, who grew up in post-war Britain, would want to navigate through all the challenges. Did she really want to manage the blowup from the Bon App disaster or Teen Vogue controversy or the fallout from that guy from Tastemade who replaced Dawn Ostroff? Did she really want to have to strategically renegotiate the deals with longtime colleagues, or even lay them off altogether? Wouldn’t she prefer, instead, to simply host the Met Ball, enjoy life near Bellport, spend more time with family, and continue her mega-bundling involvement in Democratic politics? Well, it turned out that she still wanted to do all those things while remaining committed to not only Condé Nast, but also Vogue, itself.

Through it all, Wintour proved to be an effective partner to Bob Sauerberg, Townsend’s successor, who helped manage the transition and downsize the company, and to Sauerberg’s replacement, Roger Lynch, who embarked on the financial crusade of integrating the historically separate Condé Nast and Condé Nast International businesses. In February, after years of reported nine-figure losses in the U.S., The Wall Street Journal reported that the combined and slimmed-down single Condé entity registered $2 billion in revenue and, notably, was again profitable after years in the red. Lynch, to be sure, was the C.E.O. of record during the transition, but he couldn’t have pulled off his feat of financial engineering without Wintour.

The Succession Question
As Wintour’s mandate expanded, naturally, Vogue succession conversations intensified, regardless of Lynch’s protestations that she was in her prime. Over time, the insider conversation shape-shifted: Would Eva Chen, a former protégé, return from Instagram? Would Sally Singer, a former longtime hand and briefly the editor-in-chief of T return from a new-ish perch at Amazon’s fashion business? Stefano Tonchi, the former editor of both T and W (yes, this industry is not always literary…), no longer seemed plausible after his litigious exit from Condé Nast after the sale of the former title. Virginia Smith? Mark Holgate? Later, next-gen internal talents like Chioma Nnadi would appear to be contenders. But the obvious potential successor through it all was Edward Enninful, the editor of British Vogue.

Enninful, in almost every conceivable way, seemed like a dream candidate. A Black and gay man of Ghanaian-British roots, he was a powerful visionary in an industry desperate to embrace new ideas and champion new voices. He had emerged as the wunderkind fashion editor at i-D magazine as an 18-year old, and by his 30s was the mastermind behind Vogue Italia’s 2008 issue devoted entirely to Black models and talent. He was also the creative force behind Rihanna’s Internet-breaking W cover in which she was styled as the queen. And like so many in the business, he’d cut his teeth under Wintour. Religious viewers of The September Issue will recall some of his work being reshot, perhaps too avant garde for the more commercial mandate of Vogue.

Years later, in 2017, Jonathan Newhouse, Si’s younger cousin, who ran the now-merged international wing of the business, appointed Enninful the editor of British Vogue, replacing Alexandra Shulman, who had held the role for nearly 25 years. His appointment was electrifying and historic for the industry, but it also raised the question of whether Wintour had signed off on the decision. Certainly, she didn’t have to (it’s not her company, despite her contributions), but as one of the five or so most significant players in the industry, many assumed it would be her call. Insinuations about frostiness between Wintour and Enninful subsequently amplified over the years, triggered by only-in-fashion incidents such as Queen Elizabeth’s appearance beside Wintour at the British designer Richard Quinn’s runway show, in 2018, in which both Enninful and Jonathan Newhouse were conspicuously absent. Wintour and Enninful never speak ill of one another publicly—both are far too savvy for that—but those in their respective entourages can barely conceal that there’s bad blood between them.

Anyway, this is fashion, even at the new Condé Nast—a creative and competitive business where egos are large and skin is thin. And Enninful’s stature was only growing in the industry, via his iconic cover shoots, his new memoir A Visible Man, and a recent press tour that included, among other things, a glowing profile from Maureen Dowd of all people. For some in the uppermost tiers of the creative elite, an Enninful collaboration had become far more status-defining than anything one might do with Wintour. Indeed, in the run-up to her latest album, Beyoncé chose to collaborate with Enninful, not Wintour, on a stunning British Vogue cover shoot that she would later use as inspiration for the cover of the album itself. At Vogue, such victories have the power to inspire fear and resentment among the rival camp, and reignite long-standing speculation: In an industry that is changing, and shrinking, can Wintour enjoy her deserved right to write her own last chapter while keeping a legend-in-the-making at bay?

Vogue Over All
The whispers returned to the fore this week thanks to an item in The Daily Beast, which posits that Enninful is “apparently gunning for the Iron Lady of Gloss’ plum job,” and has told associates he “believes he can do a better job than Wintour atop the Vogue brand.” Some well-placed sources inside Condé believe Camp Wintour had a hand in placing that piece, and interpret it as an effort to paint Enninful as envious and covetous lest he decide, as some fear, that he may take his talents elsewhere. (Would Wintour’s camp really leak to The Beast? Doubt it, but that’s what people think…)

The thesis of the Beast item belies some of the market realities: Wintour, given her accomplishments, is competitive but probably not threatened by Enninful; but it’s also very likely that Enninful, forward-looking as he is, recognizes that Vogue’s throne is no longer the pinnacle of fashion that it once was. Indeed, he may even be starting to feel like he’s outgrown not just his job, but one of hers too. And if he is frustrated at Condé, it may have more to do with the strictures prohibiting him from producing projects outside the magazine, doing brand deals, sitting on boards, et cetera, than with any ambition to seize control of a shrinking empire. To paraphrase Enninful’s dear friend Jay-Z: he’s not looking at her, he’s looking past her.

In any event, the party truly vulnerable to all this tension is neither Wintour nor Enninful, but Vogue itself. At this point, Anna is the business, the individual responsible for so many of the relationships, the advertising deals, the enduring status of the brand. Without her, Vogue could one day eventually become a higher-end version of The Cut, albeit with a far more storied history. And without Edward, there’s no real star to take her place when she leaves—which, given that she is 72, is something that will happen sooner than anyone inside Condé is ready to admit.

Presumably, Wintour and Enninful understand this, and so, too, does Lynch. Indeed, sources tell me the three of them met earlier today in Paris, on the sidelines of Paris Fashion Week, to talk business (the official explanation; they meet monthly, after all) but also to delicately hash out grievances. This appears to have calmed the waters, at least for the time being. They’re all adults, of course, and surely want what’s best for the business.

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