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PARIS—“Be ready, be ready, be ready!”

“Find your pace.”

“Hit your shots.”

These urgent words of advice are being directed toward Viktor Troicki from the front rows of the Bullring as he begins his match on Saturday morning. While they may sound a little basic and obvious as far as professional tennis coaching goes—it’s hard to even call it coaching in the specific sense—they also seem appropriate to the moment. That’s because Troicki is playing a guy with a knack for taking his opponents out of their games and making them forget all about their fundamentals, Alexandr Dolgopolov.

When Troicki’s advisers say “Be ready!” they're really only telling him to be ready for one shot: the drop. “All he does is hit that shot,” one of his coaches says to another. And while that’s technically an exaggeration—Dolgopolov is hitting serves to start the points—it’s only a slight one. The Ukrainian trickster and ponytailed touch artist is hitting drop shots the way Rafael Nadal hits forehands—that is, as often as humanly possible.

He’s been struggling a little with his normal backhand drive of late, so in one sense the drop is a Plan B. But you also get the feeling that this is the way he loves to play, this is what makes tennis not boring for the kid who spent his boyhood on tour with his coach father and has had a love-hate relationship with it ever since. He loves carving under the ball delicately and with varying degrees of underspin and sidespin. Loves trying to make that little “pfft” sound with his strings, the one you hear when you really slice the ball thin, catch it an oblique angle, and make the strings move, the one that usually means the ball is going to crawl over the net and die and drive your opponent up a wall.

And that’s exactly where Troicki is in the middle of the second set. He’s won the first, but been broken early in the second. He’s tried to be ready for every drop shot, every occult spin, every strange and surprising carve of Dolgopolov’s racquet, and he’s mostly succeeded. He has been ready. But in this set it hasn't been enough. Troicki tracks down Dolgopolov’s drops, but they’re so close to the net that all he can do is flip a feeble reply over the net and right into his opponent’s strike zone. When Dolgopolov brings him up to the net and passes him for what seems to be the 10th straight point, Troicki stops, puts his hands on his hips, and stares across the net at his advisers, as if to say, “I was ready, geniuses, and look what happened.”

Among the players, one word is enough to describe Dolgopolov: unpredictable. You never know what’s coming next, and that’s certainly true for Troicki today. Think of the things he must be prepared for from one shot to the next: Aside from the ever-present threat of the drop, there’s the Dolgopolov backhand that comes in with so much sidespin that it bounces straight up, like a top; the backhand with an extra helping of extreme backspin; the backhand hit like a flat, ground-hugging rocket; the slice forehand that floats; the slice forehand that stays slow and buzzes the net cord; the return that Dolgopolov brushes with reverse sidespin, like a pitcher's screwball. It’s this last shot that really shows the kind of magical feel that he has for the ball. Dolgopolov tries it out of necessity, when he’s jammed. Yet even when he’s jumping out of the way of the serve, he still makes contact softy, delicately, and manages to do something a little unusual with the ball.

But it’s an unfortunate fact of tennis that more options does not make the game easier. It just forces you to make choices, to leave things out, to think—the worst thing any player can do as he’s preparing to take his racquet back. For Dolgopolov, a brainy computer lover who has been blessed and cursed with a free spirit, it may mean having to forego some of the elements of the sport that it fun for him, that keep it from being the drag that it got to be in his early days on tour. His struggle is the struggle of the tennis artist to reconcile his idiosyncrasies and outlandlish flights of shot-making fancy with the duller needs of winning. Watching Dolgopolov, you see the limits of tennis’s version of individualism, of its opportunities for self-expression. An artist is paid to go his own way and do his own free-spirited thing. A tennis player isn’t.

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Dolgopolov and John McEnroe have little in common as personalities—Dolgo is a mellow and, at least on the surface, distinctly un-tortured artist. McEnroe, well, was not exactly like that as a person, but he was an equally idiosyncratic and artistic player, with a bizarre service motion and hands of magic. As Mary Carillo said of McEnroe after he won the famous fourth-set tiebreaker over Bjorn Borg at Wimbledon in 1980, that was the moment when he couldn’t just be the artist anymore, because he knew he could be the champion.

McEnroe found success because he felt a striver’s obligation to make the most of that talent. He thought he should win every match and went berserk when he didn’t live up to his own expectations. While Dolgopolov has found his love for the sport again, there’s little evidence to suggest that he possesses an extreme drive to succeed or a belief that he should win every match he plays. But there are positive signs for the future. Today, when he abandoned the drop shot, he won points by playing solid, first-strike, big-forehand tennis—he can do it that way, too. And when he got down at the end of the fourth set, he fought brilliantly and doggedly, saving six set points. Dolgopolov also seems to have found a similarly free spirit in his coach, Jack Reader, a shaggy, gregarious, chain-smoking Australian. Will he need a disciplinarian at some point to take him farther? It’s hard to imagine Dolgopolov, like the similarly talented and stubbornly laconic Andy Murray, responding well to that.

To me, Dolgopolov is worth rooting for, not just to see him make the ball spin like a top and drop a centimeter in front of the net, but because I’d like to see someone who can expand the game in so many directions make those directions useful; to see a guy who can do so many things with a racquet also win with one. Watching someone win is enjoyable, too, no matter how a player goes about it. Today, after all of Dolgopolov’s spectacular shots had been used up and ultimately gone for naught, I walked out of the Bullring with a new respect for his opponent, Troicki. He’s taller and stronger than he looks on TV, and a more powerful athlete. He had to do a ton of running, and watch for every kind of shot possible coming off of his opponent’s racquet. And he had to hold serve in the end after squandering six match points in the previous game. Troicki had, as his advisers said, to ignore the crazy genius across from him. He had to hit his shots and find his pace. He was ready.

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