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As Serena Williams is proving, retiring from tennis can be complicated

Serena Williams has not definitively said that she's done after this U.S. Open. (Charles Krupa/AP)

When Serena Williams was given a chance to clarify her retirement timetable after she extended her career at least one more match with a first-round U.S. Open victory Monday, she gamely deflected the question.

“I’ve been pretty vague about it, right?” Williams said with a chuckle. “I’m going to stay vague because you never know.”

With it, Williams followed a well-established pattern at the elite ranks of professional tennis: There is no pattern when it comes to retirement.

For some champions, the decision is dictated by injury; the body simply fails them.

For others, something essential withers in the heart — the compulsion to push and punish themselves daily to stay at the top.

Serena Williams, master of her mind and body, summons a champion’s resolve

For others, the decision is messy, fraught with second-guessing. Some days, they’re sure they are tapped out; other days, the competitive rush returns. And the question becomes: Why exactly quit when I can still play great tennis and, maybe once in a while, beat the best?

At this year’s U.S. Open, Williams’s anticipated retirement is being delayed by one stunning performance after another to delirious cheers of star-studded record crowds.

Ranked 605th, the 40-year-old Williams opened the tournament with a straight-sets upset of 80th-ranked Danka Kovinic that nearly quadrupled ESPN’s ratings over the previous year. Next, she ousted world No. 2 Anett Kontaveit, 26, who was 3 when Williams won the first of her Open era-record 23 Grand Slam titles at the 1999 U.S. Open.

Fans of Serena Williams celebrated the tennis stars' U.S. Open match win over No. 2 seed Anett Kontaveit in New York on Aug. 31. (Video: Reuters)

Everyone is reveling in Williams’s career resurgence — except, of course, the women across the net. It could be chalked up to magic if Williams weren’t the game’s grittiest competitor, so skilled in overcoming odds, weathering momentum swings and summoning her best when things look most bleak.

Williams has never lacked self-belief. Now, boosted by momentum and the mania of a lung-splitting, fist-pumping New York crowd, only the foolhardy would count her out against Friday’s third-round opponent, Ajla Tomljanovic, or any subsequent challenger. And it might just make her question the wisdom of walking away when she can vanquish great players.

On this point, 14-time Grand Slam champion Pete Sampras was an outlier, walking away at the peak of his powers.

The most dominant player of his era, the big-serving Sampras never competed again after he toppled his greatest rival, Andre Agassi, to claim his final major at the 2002 U.S. Open.

The decision still stuns his former coach Paul Annacone, himself a former player, decades later.

“For Pete,” Annacone recalled in a recent interview, “he finally came to the conclusion one day and said: ‘I’ve been thinking about it for a long time, but I’m done. I’m finished.'”

“I said, ‘That’s it?’ Win the U.S. Open and never play again. I don’t know how you do that. How is that even possible? But everybody is different. No matter how much success you have had or not had, everybody does it differently.”

Without big sister Venus, the Serena Williams story could never be told

Tennis fans of an earlier era were stunned by the retirement of Bjorn Borg at age 26. The 11-time Grand Slam champion was a global rock star — a shy, shaggy-haired Swede who whipped fans into a frenzy the moment he won the first of his six French Open titles just days after turning 18.

Borg also sparked a riveting rivalry with the combustible young John McEnroe, whose game and temperament were his opposite. But by his mid-20s, Borg had lost all joy in the game he once loved and quit with scarcely a word soon after he lost in the 1981 U.S. Open final.

The tennis world mourned, then mourned again when Borg’s comeback attempts in the early 1990s fizzled without a victory.

Flash forward about 30 years, and tennis was stunned by another retirement this past spring, when world No. 1 Ashleigh Barty announced via Instagram that she was walking away at 25, having achieved all she had dreamed.

“There’s no right way, there’s no wrong way. It’s just my way, and this is perfect for me to share that I’ll be retiring from tennis,” Barty said in her post.

It was, in fact, the second time in Barty’s brief and brilliant career that she had given up tennis. The first came at age 18 after realizing that the weight of expectations as a junior prodigy and the grind of travel far from home had robbed her joy.

After taking nearly two years off to play competitive cricket, Barty returned to tennis and won the 2019 French Open, 2021 Wimbledon and, in what proved the capstone of her career, the 2022 Australian Open, becoming the first Australian woman in 44 years to win her home major.

“When you work for 20 years towards something and you finally achieve that, I was thinking, ‘What else is there?’” Barty later told WTA Insider. “What more could this sport offer me? What more could I gain from playing the sport?”

Unlike Borg, however, Barty’s decision seemed to be rooted in personal satisfaction and an eagerness to get on with life. Four months later, she married her longtime boyfriend, Australian professional golfer Garry Kissick.

Said Hall of Fame inductee Chris Evert, who waited until after her 1989 retirement to start a family: “A lot of athletes retire, and they haven’t set up a future for themselves. And I think that you’ve seen a lot of depressed retired athletes.

“… For me, once I retired, I felt like every day I was on vacation for a while. I really realized how much pressure was put on a tennis player and how much I didn’t have to be intense. I didn’t have to be nervous and have that knot in my stomach every day. And then you have children, and then it’s like it’s all about them. And there’s joy. It’s like, whoa, there’s joy in your life.”

Williams drew global headlines in August for disclosing in a Vogue cover story that she was “evolving away from tennis” as her 41st birthday neared.

One of the sport’s great champions who has revolutionized the game, Williams long ago passed the mark of having nothing left to prove. At this stage, the desire to have a second child matters more, she indicated.

Even if she makes an improbable late-career run to the tournament’s second week, as Jimmy Connors did in reaching the semifinals of the 1991 U.S. Open at 39, Williams may well walk away from this year’s U.S. Open with the question of her exact retirement date unanswered.

For some time, fans have braced for the inevitable retirement of Roger Federer, 41, who has brought unparalleled grace to men’s tennis.

The widely revered Swiss champion was met with a massive ovation for simply walking onto Centre Court in a suit and tie as part of July’s celebration of Wimbledon’s 100th anniversary at its current location.

Federer has not competed since his straight-sets loss to 14th seed Hubert Hurkacz in Wimbledon’s 2021 quarterfinals, which was hardly a fitting coda for his Hall of Fame career. But after three knee surgeries, it’s unclear when or even whether Federer, now the father of four, will compete again.

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Evert, who won 18 Grand Slam singles titles, recalls her retirement as largely an inner decision, shared in advance with few people beyond her husband at the time, Andy Mill, and her agent. Feeling increasingly burned out after 17 years on the pro tour, Evert decided she would compete one final season, visiting all the cities that had been fixtures on her calendar, and walk away after the 1989 U.S. Open.

After being ousted by Zina Garrison in the quarterfinals, the two embraced at the net, and Evert waved as they walked off court together.

“It was so different in that day,” recalled Evert, now an ESPN analyst. “I mean, it’s like I just waved and walked off the court, and that was it.”

In retrospect, she said, she wishes she had savored the moment a bit more and shared her emotions with the fans. But that wasn’t her way, and it wasn’t her impulse at the time.

“Basically after I lost, I kind of wanted to just get off the court,” Evert said. “And there [was] no fanfare or anything. No parties. Nothing.”

With it, she brought an end to the sport’s greatest rivalry.

For 16 years, she and Martina Navratilova took the measure of each other — physically, tactically and psychologically — in 80 matches on clay, grass and hard-court. Navratilova finished with a 43-37 edge.

Years later, that’s not the only distinction Evert recalls about her lifelong friend Navratilova, who kept competing in singles through 1994 and made a comeback in doubles in 2000.

While Evert retired without fanfare, Navratilova got the full star treatment upon playing her last singles match — a first-round loss to Gabriela Sabatini in the WTA Tour Championships at Madison Square Garden.

Then 38 and the women’s record holder for total weeks (332) atop the WTA rankings, Navratilova was feted with a glitzy retirement ceremony at the Garden and given a Harley-Davidson.

“I was a little jealous of that,” Evert recalled with a laugh. “Not that I wanted a motorcycle — but I would have settled.”

How so?

“A necklace,” she suggested. “Diamond necklace.”

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