The U.S. Open begins Monday in New York City. Here are 10 burning questions ahead of Monday's first ball. 

By Jon Wertheim
August 24, 2019

This story appears in the Aug. 26–Sept. 2, 2019, issue of Sports Illustrated. For more great storytelling and in-depth analysis, subscribe to the magazine—and get up to 94% off the cover price. Click here for more.

You perhaps thought that tennis was an individual sport featuring head-to-head matches. But the most gripping theater in the sport—or in all sports, we would submit—is a race among three men. The derby pitting Roger Federer (20), Rafael Nadal (18) and Novak Djokovic (16) against each other to see who can win the most major singles titles is also a de facto battle for the title of men's tennis GOAT.

That the three most accomplished male players of all time compete contemporaneously means that we have the good fortune to regularly witness their greatness. It also means that every major now comes freighted with historic importance.

And the margins are impossibly slim. Last month at Wimbledon, Federer held match point against Djokovic in the fifth set of their spellbinding final. Federer reared back and hit a serve that appeared destined to be an ace. The ball whizzed through the air, but suddenly—as if to say, Nah, I'm good over here, thanks—clipped the top of the net and fell on Federer's side of the court. The crowd sighed. Djokovic exhaled. Then he won the point. And the game. And, ultimately, the match, 7--6, 1--6, 7--6, 4--6, 13--12.

The next leg of tennis's Great Race, the 2019 U.S. Open, kicks off on Aug. 26 in New York. And the state of the Slam standings is only the most obvious tournament story line to follow. Herewith, 10 pressing questions:

Can Djokovic win over the field?

Right now, the hottest stock in tennis is, unmistakably, Djokovic Inc. The Serb has won four of the last five major titles and hasn't lost to Nadal or Federer at one since 2014. Federer's balletic tennis and Nadal's lefty, spin-heavy game are instantly appealing to the casual fan; Djokovic's style is more of an acquired taste. But he's just as devastatingly effective, and maybe more so. He's the best returner in tennis. His ability to cover the court is extraordinary and unrivaled, which allows him to extend rallies and make opponents aim for smaller targets. He can all but bend spoons with his mental strength. At his best on hard courts, Djokovic comes to Flushing Meadow as the top seed, the defending champion and the betting favorite. But not the crowd favorite....

Can Djokovic win over the public?

There are, of course, no majors held in Switzerland or Spain, but Federer and Nadal routinely feel as though they are playing home games, so consistent is the crowd support for them. Then there is Djokovic, who, unmistakably, lags in the popularity rankings. While the best explanation is that he arrived late to the scene, after fans had already professed their allegiance for Federer or Nadal, the subject of Djokovic's persistently middling approval ratings in the face of surpassingly excellent tennis remains a talking point. Some athletes would profess indifference to this, or even embrace the role of WWE-style heel. Not this guy. Djokovic—and this is no knock—eagerly craves affection. As Nick Kyrgios put it earlier this year on a podcast, "I feel like he just wants to be liked so much that I just can't stand him." Maybe another U.S. Open title will endear Djokovic to the New York crowd. If not, he has some coping mechanisms. At the Wimbledon final, when the crowd rooted vocally for Federer, Djokovic convinced himself otherwise: "When the crowd is chanting 'Ro-ger, Ro-ger' I hear 'No-vak, No-vak.' It sounds silly, but it is like that."

What's Serena Williams's mind-set?

She won the first of her six U.S. Open titles (gulp) 20 years ago, as a 17-year-old. But Arthur Ashe Stadium has been the site of many disappointments as well. Serena was two matches from winning the 2015 Grand Slam when she tightened and lost, crushingly, to unseeded Roberta Vinci. Last year Serena reached the Open final—and was on the precipice of tying the all-time mark for major singles titles, with 24—when she lost strangely and controversially, after being penalized a game for calling the chair umpire a "thief." You can—and many do—still argue over whether to attribute the defeat to Serena's lack of impulse control or to the umpire's lack of swallow-the-whistle discretion. Still stuck on 23, Serena would pull off the ultimate exorcism if she were to win her 24th major in September. But she's almost 38. She plays (too) sparingly. Since her return in the spring of 2018 after giving birth to her daughter, Olympia, she's reached the finals in half of her six majors but has dropped them all. Then again, sepulchers are filled with the bones of those who have doubted Serena through the years.

Wither Naomi Osaka?

At the 2018 U.S. Open, Osaka, then 20, played valiant power tennis and kept her nerve in the final, defeating Williams and winning her first major. She then backed it up by winning the 2019 Australian Open, becoming No. 1 in the process. Since then, wins have been hard to come by. Same for motivation and happiness, as Osaka herself concedes. In a recent lengthy, know-thyself Instagram post, she conceded, "Whenever things go wrong I blame myself 100%, I have a tendency to shut down because I don't want to burden anyone with my thoughts or problems.... I can honestly reflect and say that I probably haven't had fun playing tennis since Australia and I'm finally coming to terms with that while relearning that fun feeling." Here's hoping she recaptures the fun feeling in New York.

Who’s with Coco?

Since her Wimbledon breakthrough, Coco Gauff, the prodigy from Florida, has not improved her singles ranking, currently No. 140. That's hardly a condemnation of her tennis. Only 15, Gauff is severely hamstrung by the WTA's age eligibility rules, which restrict the number of tournaments she is allowed to enter. Following one too many unfortunate collisions, the policy was created as something of a traffic light, placed at the four-way intersection of Youth, Fame, Pressure and Money. (See: Capriati, Jennifer, et al.) Despite good intentions, the policy has come under fire for a) restricting a talented young athlete's ability to capitalize on said talent and b) adding pressure to those scant opportunities when teenagers can play. Gauff—who won a WTA doubles title on July 29 in Washington, D.C., will be greeted with great fanfare. We'll see how she handles the spotlight at what might be the last pro tournament she enters in 2019.

What of the other 125 players in the men’s draw?

At Wimbledon, the Big Three, in keeping with ritual, all reached the latter rounds; meanwhile, the players ranked four, five and six—Dominic Thiem, Alexander Zverev and Stefanos Tsitsipas—each lost in the first round. No current player under 30 has won a major. Why have none of the young (or, for that matter, middle-aged) guns broken through? Explanations are manifold and not mutually exclusive. The best-of-five format favors the Big Three, giving them more opportunities to summon their superiority. Their relentless winning has demoralized everyone else. Andy Murray's mother, Judy, a savvy tennis observer, has even gone so far as to suggest that because the Big Three did not grow up with iPhones, they possess greater powers of focus and healthier relationships with social media. Whatever, we're getting restless for a challenger.

Will Nick Kyrgios come to play?

For all the debate and disagreement in tennis, you can carve out consensus here: The most talented men's player under age 30 is Nick Kyrgios. The problem is that Kyrgios hasn't figured out what to do with his talent. Sometimes the 24-year-old appears destined for No. 1—not least when he defeats one of the Big Three. Other times, he plays with a complete indifference to the match's outcome. At last year's U.S. Open, fans were treated to the bizarre (and surely unprecedented) sight of a chair umpire giving Krygios a mid-match pep talk and encouraging him to try harder. This year, Kyrgios has incurred fines, including $113,000 for outbursts in Cincinnati on Aug. 14, and pulled out of the French Open because "clay sucks." He has also won two tournaments and played at a can't-avert-your-eyes level.

Can Simona Halep continue to shine in the shadows?

At 27, Halep is a decade younger than Serena. She's not outrageous or inconsistent or confessional on social media. She plays with a subtle mix of offense and defense and moves gracefully but will not blow many opponents off the court with power. So it is that the Romanian gets very little attention. Which is a pity because she's thoroughly professional, thoroughly pleasant and, oh, right, has also been the best WTA player over the last three years. When Halep won Wimbledon in July—dismantling Serena 6--2, 6--2 in the final, in less than an hour—she assured herself entrée into tennis's Hall of Fame. She'll now try to win her second straight major and her third since June 2018.

Can doubles continue its ascent?

When the tennis salon considers its 2019 Comeback Player of the Year, it might want to focus not on an athlete but on an entire discipline. For a long time doubles has been the sport's great undervalued asset. But lately the format is enjoying a renaissance. Plenty of stars are realizing the virtue of playing alongside a partner. For instance, Ashleigh Barty pairs well with Victoria Azarenka—a former No. 1 singles player. Tsitsipas and Kyrgios recently played together in Washington, D.C. The ultimate pairing may have come at Wimbledon when Serena Williams played mixed doubles with Andy Murray. Want to work on your volleys or second serve under match conditions? Here's a way to do it—while getting paid. And if the players benefit, so do the fans.

Can tennis get out of its own damn way?

Tennis is rather like a swan. Elegant and regal above the surface; unseemly and ungainly below. As the players execute their duties on the courts these next two weeks, the sport's administrators will be locked in conference rooms at the Tennis Center and in midtown Manhattan hotels, trying to chart the future. The ATP is looking for a CEO after its previous head was the subject of a coup, orchestrated largely by Djokovic and board member Justin Gimelstob, who was facing a charge of felony battery at the time. (He since pleaded no contest and resigned his board spot.) The International Tennis Federation is holding its presidential election with ethical questions swirling around the incumbent. The USTA also seeks a new executive director, pitting outsider candidates against insider candidates. Tennis's congenital dysfunction is as predictable as the excellence of the Big Three. And neither shows signs of abating.

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