The first time Serena Williams held up the winner’s trophy at the US Open, the world was busy worrying about Y2K.

We were all just getting acquainted with MSN Messenger and a whole new form of mobile communication. Bill Clinton was President—he’d been impeached and acquitted by the Senate a few months before—and by then, almost everyone in the country had seen the summer’s big blockbuster, Star Wars: Episode 1—The Phantom Menace. 

In those final, sweltering days of summer 1999 in New York, September 11th was just another day on the calendar. No one had heard of an iPhone—it wouldn’t be invented for another eight years. If you’d asked someone if they were on Facebook or had Tweeted recently, you’d be met with blank, slightly concerned stares. 

Summer 1999 is when 17-year-old Serena arrived on the professional tennis scene with a bang.

She won the US Open that year, beating No. 1 ranked Martina Hingis in straight sets. It was the first of her now-23 Grand Slam titles, the most of any player, male or female. By now, she’s become a household name, tennis fan or not. 

At the 2022 US Open, she walked on court at Arthur Ashe Stadium first round to thunderous applause as the greatest female athlete of all time. It’s the final run for 40-year-old Serena; she announced she’ll retire from professional tennis after this year’s US Open.  

And a big reason she’s walking away was sitting courtside for that opening round match, wearing a sparkling tennis outfit to match her mom’s, and adorably snapping photos with a pink checkerboard-patterned camera.

Look at Olympia cheering for Serena 🥹😭 pic.twitter.com/aCrZIMdggr

— Cool Moms (@cool_momz) August 30, 2022

In the personal essay in Vogue magazine announcing her retirement, Serena wrote about 5-year-old daughter, Olympia: “We’re in my car, and she’s holding my phone, using an interactive educational app she likes. This robot voice asks her a question: What do you want to be when you grow up? She doesn’t know I’m listening, but I can hear the answer she whispers into the phone. She says, ‘I want to be a big sister.'”

In Vogue’s September issue, @serenawilliams prepares to say farewell to tennis on her own terms and in her own words. “It’s the hardest thing that I could ever imagine,” she says. “I don’t want it to be over, but at the same time I’m ready for what’s next” https://t.co/6Zr0UXVTH1 pic.twitter.com/YtGtcc18a9

— Vogue Magazine (@voguemagazine) August 9, 2022

Serena has talked openly about her desire to grow her family with husband Alexis Ohanian—and how the tension between that and the demands of a professional tennis career brought her to a crossroads. 

But, as Serena wrote, the way forward was clear: “The fact is that nothing is a sacrifice for me when it comes to Olympia. It all just makes sense. I want to teach her how to tie her shoes, how to read, where babies come from, and about God. Just like my mom taught me.”

It remains to be seen if Serena will cap off her career with a 24th title and get the storybook ending I’m sure she dreams of, the one fans would love to see.

Honestly? It doens’t really matter. 

Because Serena’s been teaching us since before we all got our first flip phones. About tenacity and grit. About comebacks and rising above. About family and ferocity. About work and motherhood.

And it’s been quite a ride. Best of luck in your next chapter, Serena! 

That winning feeling. #Serena pic.twitter.com/xJ4YUdi1Fj

— US Open Tennis (@usopen) August 30, 2022

No matter what happened, this was the image that made tonight extra great. #Serena ⁦@usopen⁩ pic.twitter.com/Vs2wPjfCyz

— Sherrilyn Ifill (@SIfill_) August 30, 2022

Watching Serena play tennis legit makes me want to cry. It’s a performance. it’s art, it’s excellence, it’s poise, it’s an experience, it is EVERYTHING!!!! Rooting so hard for every single point

— Taylor Rooks (@TaylorRooks) August 29, 2022

Serena is rightly in the spotlight, but this @andscape piece from Nikki Giovani about Venus' impact on Serena is beautiful.

"Having a big sister who loves you enough to be your teacher is great."

Yes. Yes. YES #USOpen https://t.co/8Xu8Dz0LEv

— Britni Danielle (@BritniDWrites) August 30, 2022