The battle for Anna Wintour’s Vogue empire

When Anna Wintour announced she was stepping down as editor-in-chief of Vogue in June, it appeared to be the end of the ice queen’s reign. Yet Wintour retained her large, chintzy corner office as well as her two other roles – as Condé Nast’s global chief content officer and Vogue’s global editorial director.

If you looked closely, you might have seen a steely determination lurking behind her trademark sunglasses, the look of a generational editor intent on more power – and perhaps even revenge.

The Condé Nast Union naively regarded Wintour’s move as that of a then 75-year-old drifting into quiet retirement, the old guard surrendering to youth. The union, formed in 2022 and seemingly run by the most radical young left-wing journalists in the company, has quickly grown in power and influence. But various Condé Nasties have informed The Spectator that the union has become a parasite which threatens to consume its host.

When Wintour decided to close down Teen Vogue by folding it into Vogue.com – officially to consolidate resources – it was no surprise that a dozen angry young Jacobins from the union confronted the head of HR, Stan Duncan, about the layoffs of six staffers. However, instead of leaving with Duncan’s head in a basket, it was the four most vocally aggressive employees – lionized now as the “Fired Four” – who were guillotined: fired immediately and without ceremony. They learned the hard way that Condé is still a monarchy.

And, according to insiders, Wintour is only just getting started. Condé has filed a grievance against the union with the National Labor Relations Board. Insiders believe Wintour and CEO Roger Lynch are planning to throttle it with litigation after finally making “a business decision to face down the union.” This is a fight the company must win, sources say, if it is to have a future.

Those sources believe Condé has, “against its better judgment,” played ball with the union for too long. When the union threatened to form a picket line at last year’s Met Gala, the highlight of Vogue and Wintour’s social diary, Condé caved on the day of the event. The union, which represents more than 500 staffers at publications such as Vogue, GQ, Vanity Fair and Architectural Digest, won a $61,500 starting salary floor, $3.3 million in total wage increases and a host of benefits. Rather than assuaging the union, the agreement only emboldened its leaders. “The way the union won its settlement gave the members a sense of undue power,” one source said. “Some union members now go to work and they do their jobs – but only just.”

Part of the problem is that members of the union are not given an incentive to work hard. They are only meant to carry out their precise job descriptions rather than earn a promotion or pay raise, as the union now negotiates pay raises en masse. However, its members found enough time to compile a union “zine,” a highly produced pamphlet which provided advice on how to navigate “difficult conversations with managers.”

“Some people behave in the office as if the company owes them and their jobs are protected, they don’t seem to understand they work for a business,” another Condé Nast source said. “Teen Vogue was a great example of what staffers wanted to write about rather than what the magazine should have been writing about. The traffic had started to crater on Teen Vogue and it had become unsustainable as a business.”

The magazine hasn’t been in print since 2017 (its final issue featured Hillary Clinton on the cover, the kiss of death), but its website continued to churn out content that insisted to young girls and they/thems that woke political views were each season’s must-have accessories. The attitude of its staff was one of entitlement: they seemed to see journalism as a noble calling, not a business, therefore subscriptions had nothing to do with their salaries.

Among the union’s grievances, including that the publication is disproportionately firing “BIPOC, women or trans” employees, is that it no longer has any writers covering politics. Maybe that’s the point. Teen Vogue’s venture into Great Awokening-style politics has run well past its expiration date as the publication finds itself out of step with readers, advertisers and even some employees. Insiders say the dogmatic left-wing politics at Teen Vogue created a hostile workplace. “Internally, Teen Vogue will not be missed by a number of staffers who were tired of how inhospitable it was to staff who were not aligned politically. The way they wrote some articles about October 7 deeply upset some Jewish staffers, who questioned their ability to continue working for the brand,” says one insider.

Teen Vogue’s anti-Israel bias was called out last year by Vogue entertainment director Sergio Kletnoy in an email to Wintour and Lynch. While Wintour has not commented on Teen Vogue’s stance, it contrasts markedly with her own actions: she immediately parted company with Vogue contributing editor-at-large Gabriella Karefa-Johnson for an anti-Israel rant the day after October 7. Other brands at Condé are struggling to turn the smallest of profits – could they be on the chopping block next? Some staffers wonder whether the decay has already gone too far to save the business. Condé Nast is reportedly on target to miss its $1 billion revenue target this year. Global advertising revenue is down, and so is web traffic. While “go woke, go broke” holds true, Condé’s search traffic has also been hit hard by AI overviews.

Defeating the union is only part of the solution if Condé is to survive. Talking about an influx of British editors to the US, Wintour said Americans tend to think of British journalists as “cutthroat” and turn to them “when American media companies feel they need to fight to stay relevant, or profitable.”

We will see if Wintour still has that flintiness to her. The editorial shake-ups at CBS and the Washington Post are signs the age of liberal consensus in the media is over. Tough decisions are in store for publications if they want to stay competitive. When Americans can get their news for free from podcasts and social media, traditional outlets have to offer them something they’re willing to pay for. It turns out that teen angst and student politics don’t sell – even to teenagers.

This article was originally published in The Spectator’s November 24, 2025 World edition.