How Anna Wintour Befriended Serena Williams

Vogue's September issue cover story about her retirement was decades in the making.

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Serena Williams covers the September issue of Vogue, in which she makes the major announcement that she’s retiring from tennis. As a testament to the impact of this story — perhaps one of Vogue’s biggest scoops ever — The New York Times sent an email news alert about Williams’s retirement minutes after Vogue, then published a slew of articles about it. The cover reveal was a pleasant surprise after chatter in the Fashion Spot that it would feature Taylor Swift or Jennifer Lawrence. Williams is not new to the cover of Vogue or fashion magazines, making her an unsurprising choice, but her retirement announcement was stunning. Coupled with a pitch-perfect photo shoot, it made for a September issue reveal that could have only been architected by editor-in-chief Anna Wintour, a longtime friend and confidante to Williams.

The story is Anna’s Vogue at its best. The photos of Williams by Luis Alberto Rodriguez are in equal measure gorgeous, unfussy, powerful, memorable, and joyful. The simple cover image of Williams in a blue Balenciaga gown folds out to reveal her daughter Olympia peering out from her mom’s train.

The article is an as-told-to by Rob Haskell. Williams says:

I have never liked the word retirement. It doesn’t feel like a modern word to me. I’ve been thinking of this as a transition, but I want to be sensitive about how I use that word, which means something very specific and important to a community of people. Maybe the best word to describe what I’m up to is evolution. I’m here to tell you that I’m evolving away from tennis, toward other things that are important to me.

As I report in ANNA: The Biography, Anna has amassed so much power partly through networking that has led her to friendships with Serena Williams and a slew of other hugely influential, talented, famous, and powerful people. These connections enable Vogue’s access to superstars like Williams that magazines are increasingly hard-pressed to gain.

In the 2010s, celebrities started shifting away from making life announcements in magazines and traditional media channels and toward posting to their own social media accounts instead, thereby juicing their followings. Now, they’re even catching onto the magic of newsletters, Jennifer Lopez announcing her marriage to Ben Affleck in hers, called On the J Lo. Williams announcing her retirement with this story and photo shoot is an access flex truly unique to editors with tenure and status like Anna. A star like Williams, of course, has choices about where and how to make announcements like this — and she chose Vogue.

Williams’s name was on a list of close friends and colleagues that Anna’s rep suggested I interview for my book, and I’ll never forget our phone conversation, not only because it’s Serena Williams but also because it took place on Saturday, November 7, 2020 — the day the presidential election was called for Joe Biden. The conversation we had makes it easy to see how Vogue would end up publishing this major story over any other outlet.

Williams remembered first meeting Anna in her office prior to her debut Vogue photo shoot for the May 1998 issue. “I don't think I even quite understood who [Anna] was,” said Williams, who was just 16 years old at the time.