Wimbledon Preview: Roger Federer and Naomi Osaka Are Two Sides of the Same Coin

This is a strange time for tennis. There is not much of an appetite for small successes. There are players who play for history, and then there’s everybody else. Of course, there is no better time to talk about Big Legacy than during Wimbledon, a sporting event particularly obsessed with tradition and prestige and image. Competing here and winning here is supposed to mean everything. Bjorn Borg lost his crown at Wimbledon in 1981, and it seemingly broke his will to compete. In 2002 Pete Sampras, suddenly having lost two steps, was knocked from his last Wimbledon in the second round, playing on Court 2. The pressure here is supposed to be unbearable, because this, the Rolex commercials tell us, is where legacies begin and end.

The second seeds in this year’s singles tournaments are both History Players, but they’re at opposite ends of their careers. Roger Federer is seeking a ninth Wimbledon; his rivals are still going strong and nipping at his heels in the career majors count, but his track record is already unimpeachable. Somehow, it seems like he’s existing in a space apart from the pressures that Wimbledon traditionally imposes. Naomi Osaka, alternately, is the next big thing, but she’s lost an awful lot lately. This is where she’s supposed to step up and conquer a big moment, just like all the greats do. The two are facing down the tournament’s implicit ethos: At Wimbledon, you’re supposed to want something that you can’t have.

It’s a little bizarre to watch Federer nowadays, not just because he pops up on practice courts wearing Street Fighter T-shirts, but because every time he plays it seems like there’s nothing at stake. Federer has gotten older, but hasn’t he made it look sort of nice?

He’s won three tournaments this year and he’s ranked third in the world. He looks healthy, he still glides to the net, he still sweeps through his half volleys, and he still won the tune-up in Halle, his 10th. After three years of skipping the clay season in its entirety, he returned to Paris in May to play a major on a surface he has never particularly cared for; he made the semifinals, stopped only by Rafael Nadal. If this is supposed to be a disappointing season, it doesn’t feel like it.

Watching Federer play Nadal, especially on clay, and especially at Roland Garros, gave me fits for years. As a young Federer partisan in the aughts, I spent each spring hoping for an upset at the French Open, and would then spend days seething when it didn’t come, mouthing off at the TV about time taken between serves or Nadal’s distracting, belated groans. This year, though? Nadal’s three-set win wasn’t heartbreaking. The match was entertaining if not particularly competitive. It was fine. Federer, at 37, had showed up to a major on his least favorite surface after a multiyear layoff and coasted to within spitting distance of the final. Jimmy Connors, at 39, made the semifinals of a major on his favorite surface and we got a 30 for 30 about it. What has made late-late stage Federer so freeing to watch is that he is in a position to contend for every tournament while also clearly having nothing left to prove.

At most tournaments, he’s asked about his future: How are you feeling? Did you play on clay this year because you’re never coming back? Do you think you’ll be retiring soon? He parries most of them with a smile. He says only that he won’t have a retirement tour and that he wants to leave the game on his own terms. He says that he doesn’t need to go out on top, that he would have retired after winning the Australian Open in 2017 if he’d been worried about bookending his legacy. These seem like silly questions to be asking a player who, by most standards, is having a very successful and healthy season. But who can blame the pool of reporters that have to make sense of this whole thing? Has any athlete ever won this much while also truly, seemingly being fine with not winning?

Naomi Osaka makes a lot of things seem fun, but tennis recently hasn’t seemed a light and breezy pastime for her. Everything happened so fast; last year at Wimbledon she was seeded 18th and lost in the third round. And then, in a blink, the two majors, the top ranking, the commercials, the swoosh, the photos with LeBron.

For Osaka, a shy, goofy 21-year-old who Instagrams about watching The Prince of Tennis, perhaps the newfound global fame has been a little overwhelming. That’s understandable. Osaka is the only player outside of the established power structure on either the men’s or women’s tour to put together a claim as a generational talent in quite a long time.

In any time, simultaneously being a kid and being the world’s no. 1 would be enough to shake even the steadiest minds. But Osaka has already won more majors than most of her competitors. In doing so, she has become a future projection of herself: a player in the Federer template.

The pressure has taken its toll the past few months. Since winning in Melbourne, she hasn’t made another final, and at times has looked strangely lost against inferior opponents. At the French Open, in her first-round match against a player ranked 90th, she dropped the first set at love before rallying to win. In the second round of a grass tune-up event in Birmingham, England, she fell into a 0-5 hole in the first set against 43rd-ranked Yulia Putintseva before eventually losing the match in straight sets.

After the tournament, she lost the no. 1 ranking to Australian Ashleigh Barty, the 23-year-old who won in both Birmingham and Paris. Osaka enters Wimbledon as the fourth or fifth betting favorite to win the title, which would be her first. As much as she has to gain by winning the sport’s most prestigious tournament, if she loses, she won’t have the luxury of doing so in anonymity. But it’s important to remember that not every breakthrough moment happens at the right moment. Maybe Osaka’s best is still a little ways away.

If you remember Lleyton Hewitt, chances are your memories of him are a little blurry. There was a ball cap, an Aussie-inflected come on, a stretched, open forehand, but that’s mostly all that’s left in the collective mind’s eye. For the most part, Hewitt is a footnote now, playing doubles with Federer’s tire tracks still showing on his face. But at the turn of the millennium, Hewitt was ascendant. He looked a lot like Osaka: 21 and powerful, the pride of a nation, the world’s top player, and the winner (already!) of two slams: the U.S. Open in 2001 and Wimbledon in 2002.

Now, though? It’s hard to even find footage of Hewitt’s win over David Nalbandian in the 2002 final. The excitement that surrounded his early career evaporated. It’s hard, now, to imagine a young player winning two slams and not becoming an athlete of historical importance; pretty much every player who’s gotten on the international radar as a youngster over the last 15 years has become a world beater. But that’s a large and probably outsize expectation to put on Osaka (or whoever is supposed to carry the game into the 2020s).

Federer, in his (very) early days, wasn’t the anointed one. Among his cohort of young players, he came into focus rather late. Marat Safin, at 20, won the 2000 U.S. Open, shellacking Pete Sampras in the final. Hewitt won his two slams before Federer had even reached a major semifinal. In 2003, Andy Roddick, not Federer, was the year-end no. 1.

Federer had his breakthrough moment in 2001, at 19, knocking off Sampras, his childhood hero and the four-time defending champion, in the fourth round at Wimbledon. But he wasn’t ready to become himself. He promptly lost in the next round to Tim Henman (Tim Henman!) and then lost in the first week of the next seven majors.

This is all to say that Osaka’s paths through the multiverse could end up anywhere, but it’s been a while since a player has showed this kind of promise. Tennis wants an avatar for its next phase, and Wimbledon is a place that takes particular pleasure in turning each edition of its tournament into a rose-colored pivot point for the history of the game, scored with strings and covered in gold trim. Potential and pressure have always come as a package deal. Roger Federer wasn’t always Roger Federer, so Naomi Osaka might not yet be Naomi Osaka. Perhaps this Wimbledon is where that will change.