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Insider: Even at 70, Vogue’s Anna Wintour is still ‘Machiavellian’

Sunday is Anna Wintour’s 70th birthday and she apparently only wants one thing: “She’s hoping for a lot more grandkids,” said a colleague of the legendary Vogue editor.

“You would have thought Anna might have cut back her hours after becoming a grandmother,” added the colleague of Wintour, who is granny to Caroline, 2, and 9-month-old Ella, the daughters of Wintour’s son Charlie Shaffer, 34, and his wife, Lizzy. “But she hasn’t. She still doing it all.”

Indeed, Wintour shows no signs of inching toward retirement. In addition to running Vogue and shepherding Condé’s entire stable as the global content adviser, she stars in myriad videos on Vogue.com and YouTube, oversees the annual Met Gala — which benefits the Anna Wintour Costume Institute at the Metropolitan Museum of Art — and just led a 12-part series for MasterClass, the online learning academy, called #HowToBeABoss. She’s been the fashion design consultant for the Tony Awards over the past five years and the native Londoner was named a Dame by Queen Elizabeth in 2017.

“She’s not just aging gracefully,” said one Vogue writer who requested anonymity. “She’s aging fashionably. She’s changing the whole game of who can wear what at what age.”

“Anna knows how epic this [birthday] is,” said the colleague, who has known Wintour for many years. “But she’s never played by the rules so why would she start now? Just like she’s reinvented everything else, she’s reinventing 70.”

Last week, New York Magazine published a scathing account of Condé Nast’s decline, revealing losses of $120 million in 2017. This year alone, the company has sold Golf Digest, W and Brides, after shuttering the print versions of Glamour, Self and Teen Vogue in recent years.

While rumors of Wintour’s retirement have swirled in Manhattan’s power circles for the past few years, one well-placed source believes the icon is key should the Newhouse family that owns Condé Nast ever decide to sell the company.

“They’re dependent on Anna’s glam image,” said the source.

(A Condé Nast spokesperson referred The Post to this quote: “Condé Nast has not been, is not, and will not be for sale,” Steven Newhouse told New York Magazine.)

But some feel that Wintour, who behind her signature sunglasses has long been known as the most enigmatic and unknowable woman in fashion, is spreading herself too thin. The New York Magazine story described her hosting a breakfast in her office for fifty women on the “Vogue100” — a group that appears to be a prestigious honor list, but is really a membership program with access to exclusive events and parties, costing $100,000.

She’s never played by the rules so why would she start now? Just like she’s reinvented everything else, she’s reinventing 70.

 - A Vogue writer

“I have a jewelry-designer friend who got an invite [to be in the Vogue100],” said one former Condé editor who now works at Hearst. “She was so flattered until she realized she was being asked to pay a hundred thousand dollars for the right to get 15 minutes with Anna.”

Wintour has also taken heat for supporting the hiring of former New York Times Book Review editor Rad­hika Jones to be the editor-in-chief of Vanity Fair after longtime editor Graydon Carter resigned. Under Jones, the magazine has been the subject of much criticism. As New York Magazine reported, “The critiques of Jones’ Vanity Fair came hard and fast: She’d sucked the glamour and mischief out of it and replaced it with bland, earnest celebrity virtue signaling. The magazine’s stories rarely seem to break through the noise.”

“I’m convinced she’s trying to kill Vanity Fair! Because as Vanity Fair declines, Vogue looks better,” said a Vanity Fair source. “She’s Machiavellian.”

“That could not be further from the truth, Anna has been a champion of Radhika from day one,” said a Condé Nast spokesperson.

A second Vanity Fair source calls Wintour’s oversight a conflict of interest.

“They need to separate her out as the editor of Vogue and the [US] artistic director of Condé Nast,” said the second Vanity Fair source. “It’s a total conflict to have both those jobs. She’s made a disaster of every other [Condé] magazine — they all look just like Vogue.”

Still, said one Wintour source, “Anna is surrounded by sycophants.”

As for her birthday, said the media colleague, “Anna’s very big on her friends’ and family’s birthdays but she’s never been big on her own. She’ll [likely] celebrate with a small group at a restaurant or at a small dinner in her townhouse on Sullivan Street.”

Among her close circle of friends are Anne McNally, the Vanity Fair writer and ex-wife of former Indochine and Odeon restaurateur Brian McNally; socialite landscape designer Miranda Brooks; and artist Hugo Guinness. The media colleague predicts Wintour will also likely celebrate with her children, their spouses and her granddaughters at her 62-acre weekend home in Mastic Beach, LI.

“Anna is very family-oriented. Her family are the only people she trusts,” said the media colleague.

Wintour’s daughter, Bee Shaffer, 32, works for the Ambassador Theatre Group, which owns, among other properties, Broadway’s Lyric and Hudson theatres. Bee married Francesco Carrozzini, son of the late Italian Vogue editor Franca Sozzani, last year. Charlie Shaffer, Wintour’s son, is a doctor. Both are the product of Wintour’s 1984-1999 marriage to child psychiatrist Dr. David Shaffer.

One person who won’t likely be at any party: Shelby Bryan, Wintour’s longtime paramour whom she met in 1999 while both were married to other people.

“When the affair went public, she was embarrassed — but it only added to her allure,” said one former Vogue employee. “They had a very combustible connection.”

But in 2013, it was revealed Bryan owed the IRS some $1.2 million in back taxes.

“That was the beginning of the end,” said the Wintour source. “He started to become a liability. It’s been quite a while since they’ve been seen together.”

There have been rumors that the editor is involved with British actor Bill Nighy — “kind of a Shelby look-alike,” said the Wintour source — with the two spotted together at plays in New York and London.

In her MasterClass, Wintour — who has had a version of the same bob haircut since she was a teenager — reveals the secret of her success: discipline. She rises at 4 a.m., plays an hour of tennis at 5:45, then gets her hair and makeup done before going to work at Condé’s One World Trade Center headquarters. Her breakfast consists of “Starbucks,” she said, while lunch is a hamburger with no bun. By 5 p.m., after a meeting-crammed day, she’s heading home to her Sullivan Street townhouse with what she calls her “magic box of tricks”: layouts, photos and sample pages from Conde’s various magazines. Her social life consists of work events or small dinners, and she’s in bed every night by 10 p.m.

While some people were shocked she would drop her icy veil to do the MasterClass, the former Vogue employee thinks it was simply time. “I think Anna figured she was the subject of so much gossip, a movie [“The Devil Wears Prada”] and two documentaries [“The September Issue” and “First Monday in May”], she might as well use it to her and Condé’s advantage. At this point, she’s almost bigger than the brand.”

That said, according to her longtime colleague, Wintour still has her eyes on a political ambassadorship.

“She needs a graceful exit strategy. Her next move has to have the appearance of even more cachet,” the colleague said. “But given that her current [presidential] candidate of choice is [long shot] Pete Buttigieg, she may not have a friend in the next White House.”

According to a Vogue spokesperson, “Anna has not chosen a candidate.”

But it could be hard to give up her visibility, said a former Condé editor.

“Anna could get six board seats — at Estée Lauder, at Apple — and make half a million a year for a few meetings. But then she’d be disconnected. Her access would be cut off. The invites would stop coming and the phone would stop ringing. She couldn’t handle that.”

On Nov. 17, Wintour is getting one of her top honors yet: She will be one of the honorees of the Smithsonian’s National Portrait Gallery American Portrait Gala, alongside the likes of Jeff Bezos and Lin-Manuel Miranda.

Her friends say that, despite being one of the most famous women in fashion, Wintour is still misunderstood.

“She gives everyone around her a seat at the table. And she’s incredibly charming when she needs to be,” said the Wintour source. “She can be a real flirt.”

A member of Wintour’s inner circle seconded that.

“People don’t understand Anna, which is fine, she doesn’t need them to. But she is actually shy, kind, loyal, a great friend, fiercely intelligent and cultured beyond belief,” said the inner-circle source. “I keep telling her the best thing she could do now is write a book. Many books. Then she’d have ‘bestselling author’ to add to her list of accomplishments.”

Wintour through the years

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1973: Anna Wintour's fashion career began at UK magazine Harpers & Queen.Fairchild Archive/Penske Media/R
1973: Wintour, right, at Madame Gres show, moved to NYC's Harper's Bazaar in 1975 and was fired after nine months.Fairchild Archive/Penske Media/R
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1985: This was the year that Wintour -- here with designer Jean Paul Gaultier -- became editor-in-chief of British Vogue.Getty Images
1996: After taking over American Vogue in 1988, Wintour (right, with Ralph Lauren and Princess Diana) really began her fashion-icon ascent.UK Press via Getty Images
1999: Amoung Wintour's biggest achievements is the Met Gala where she rubs elbows with celebs such as Elizabeth Hurley.WireImage
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2015: Wintour, with model Karlie Kloss at a Council of Fashion Designers of America event, helped launch the CFDA/Vogue Fashion Fund Awards.Getty Images
2012: Bill Nighy & Anna Wintour at London Fashion Week.ZUMAPRESS.com
2018: Wintour with her daughter, Bee Shaffer.(Credit too long, see caption)
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