Farewell Serena – After 23 Years the Singular Star Says She’ll Retire

Photo by Getty Images

Bill Simons

Today Serena told us, “I’m terrible at goodbyes, the world’s worst.”


Of late, we’ve seen, in her inevitable journey through the twilight of her career, a powerful, though not flawless, command.

She won the 2017 Australian Open while two months pregnant. She swept aside 1,001 questions – Is the end near? When are you going to retire? “You’ll be the first to know,” she would inform one reporter after another.

Now in Vogue, in her own words, the 40-year-old indicated that she may well step aside after playing the US Open and she offered her thoughts on at last letting go, after 23 tumultuous and historic years. Newsflash: it’s hard. She tells us that her passion has shifted. She now loves being a feminist venture capitalist in her own small, all-female company, Serena Ventures. It has raised a whopping $111 million and just made a big move: it brought on a guy, in what she called “a diversity hire.” 

Serena recently asked Tiger Woods about retiring. “Give it two weeks [of training],” said her superstar friend. “Go out there and give it your all.” Serena did, and reported that after seven months without tennis it was “magical” to pick up her racket. She recalled the core dynamic of her passion. “I love to win. I love the battle. I love to entertain…I love the performance aspect of it – to be able to entertain people, week after week.”

She’s mastered the art of drowning out the noise of the crowd, yet feeling it: “Night matches in Arthur Ashe Stadium at Flushing Meadows. Hitting an ace on set point.”

But the point of her Vogue piece is the “R” word. She can’t talk with her parents about it. It’s a taboo with her husband Alexis – tears flow. She can reflect on it only with her therapist. She confesses, “There is no happiness in the topic for me – there’s a great deal of pain.” And Serena knows about both pain and bliss. She recalled, “I went from a C-section to a second pulmonary embolism to a grand slam final. I played while breastfeeding. I played through postpartum depression,” she said.

A year or two ago, Roger Federer spoke of retirement, saying, “I don’t think the exit needs to be that perfect, that you have to win something huge…and [then] you go, ‘OK. I did it all.’ It can be completed in a different way, as long as you enjoy it.”

Serena said, “I want to be perfect. I know perfect doesn’t exist, but whatever my perfect was, I never wanted to stop until I got it right.”

We are in an era when the five players who have shaped 21st century tennis – Venus, Serena, Roger, Rafa and Novak – are, in varying ways, approaching the end. 

In the past, players have stepped down in vastly different manners. Boris Becker whispered into Pete Sampras’ ear at the net after a Wimbledon loss. Li Na, Flavia Pennetta and Marion Bartoli departed right after winning Slams. Bjorn Borg, and just this year Ash Barty, left in their mid-20s, at the height of their careers. Chris Evert and Stefan Edberg merely offered poignant farewell waves. Jimmy Connors just faded away.

Serena admits she wanted to beat Margaret Court’s fabled record of 24 Slams. She says, “The way I see it, I should have had 30-plus Grand Slams.” Four times she’s faltered when she was in a Slam final and had a shot at equalling Court’s record. Oh, well, she seems to sigh, “I didn’t show up the way I could have…But I showed up 23 times, and that’s fine.” 

Serena reflected on “the fan fantasy” where she would have won this year’s Wimbledon and the upcoming US Open, “and then at the trophy ceremony say, ‘See ya!’…But I’m not looking for some ceremonial, final on-court moment.

Serena, who has won 73 career titles and is now No. 276, yesterday in Toronto won her first match in 430 days. On Instagram she said, “The countdown has begun,” and “I’m gonna relish these next weeks.” She wrote in Vogue, “I’m torn. I don’t want it to be over, but at the same time I’m ready for what’s next.” If she were a guy, she noted, she wouldn’t have to choose between family and tennis.

She also shared what has long been apparent: “I’ve built a career on channeling anger and negativity and turning it into something good.” And what is also good is her family. She adores all the delights of mothering. Playing tennis was a sacrifice and now family comes before tennis. And she wants to grow her clan and not play tennis while she is pregnant.

Serena may be blunt, but she doesn’t like the obvious. The straight path is not her road. Making it easy is not her manner. Plus, she loves to tease. She lost to Venus in a junior match but got her older sister to give her the winner’s trophy. 

Her Vogue article doesn’t say, “I am retiring now.” Her farewell ode has a bit of subtlety. She says, “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.”

Over the years, there have been many great takes on retirement. Justine Henin said, “I don’t need the adrenaline of competition to be happy.” Time and again Venus told us, “I’m good at tennis. What else am I going to do?” Actress Bette Davis said, “I will not retire as long as I have my legs and my make-up box.” 

Serena notes, “My whole life, up to now, has been tennis.” Now she looks forward to what she calls an “evolution” or “transformation” after playing the US Open.

In the end she echoed Andre Agassi. In 2006 at a packed Arthur Ashe Stadium the retiring icon the crowd, “You have given me your shoulders to stand on, to reach for…dreams I could have never reached without you. I will take you and the memory of you with me for the rest of my life.”

In Vogue, Serena bid farewell in her own touching way, telling her legions of fans,  “You have carried me to so many wins and so many trophies. I’m going to miss that version of me, that girl who played tennis. And I’m going to miss you.”

And we will miss a battler like no other, who emerged wearing beads and went on to become a proud queen, the imposing GOAT, a loving mother, an adept venture capitalist and the greatest younger sister in sports history. 

We will miss a transformative champion who showed us that bold women can wear what they want, show the fury they feel, fight and thrive in their own magical way and just maybe capture 23 Slams, raise $111 million and win a Slam with a baby in their belly.



  1. What other American has embarrassed our country like she did in the semis at the US Open when she threatened to put this “f..ing ball down your f..ing throat if you do that again” to a 95 lb Asian American lines woman who had called a legitimate foot fault on her…

    Her apology was of course belated. And of course qualified and underwhelming.
    Even MacEnroe and Conners never threatened an official. Had an NBA, MLB or NFL player done that they would have been severely punished. Serena was fined an amount less than she received for reaching the semis!
    Anyone can err (even Will Smith). One’s character should be determined by their subsequent actions and words.
    Venus in the other hand has NEVER behaved like that- even when the head official miscalled the score in a critical finals tiebreak at Wimbledon. Even when she was the victim of a scam when involved in a fatal MVA which wasn’t her fault.
    Yea Venus; good riddance to the narcissist thug Serena .


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