In the twilight of his career, where does Novak Djokovic go from here?

Novak Djokovic is in a quandary, a victim of his own greatness. He’s caught between a rock named Carlos Alcaraz and a hard place named Jannik Sinner, a solid world No. 4 after a decade-and-a-half spent even higher in the ATP pecking order. His skills are undiminished, but is no longer the paragon of vitality, fitness, and stamina that he once was. A raft of young talent is also on the move, yet Djokovic is determined to soldier on.

And why shouldn’t he?

“Novak was probably the third-best player in the world this year,” Tennis Channel analyst Jimmy Arias told me in November, referring to Djokovic’s status as a semifinalist at all four Grand Slam events of 2025. “He’s not that far away, it just feels like he is, at least from Alcaraz and Sinner. I wouldn’t want him to be a player that slowly fades away and he’s ranked No. 50 and playing in the US Open. But I would like to see if he can get that 25th major if he gives it [at least] one more year.”

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Djokovic, though, seems uninterested in that timetable. He has set his sights on competing in the 2028 Olympic Games in Los Angeles. At his last tournament appearance, in Athens, Greece, Djokovic told reporters: “Since I’ve achieved absolutely all possible goals… maybe ending up at the Olympic Games with the Serbian flag, that would be nice.”

The logistics of how Djokovic could get there from here are complicated and perhaps even perilous. He could certainly compete in the Olympics without enjoying direct entry. His record also guarantees him a wild card for life at any Grand Slam event. But if he still hopes to win the major that would break his 24-Slam deadlock with Margaret Court, or even just to keep his game title-ready, he will have to make some tough decisions.

The most critical choices center on the only tournaments that, he has said, really matter to him: the four majors.

“How do you show up ready to go? What did you do in the past? What tweaks do we need to make? Those are the questions Novak and his team have to decide,” elite coach Craig Boynton told me recently. “There are undeniables here [regarding Djokovic’s age and fitness]. So maybe start with, ‘What did you do before the Australian Open last year?’”

January 2025 may seem like the distant past, but Djokovic bamboozled Carlos Alcaraz in four neat sets in the Australian quarterfinals of 2025. That result proved bittersweet, though, because it triggered one of Boynton’s “undeniables.” Djokovic suffered a left-leg muscle tear during the match. He subsequently retired from his ensuing semifinal after Alexander Zverev won the first set.

Novak is in a part of his career where he's playing for his legacy. When you're in the midst of that, you feel like you can do it. Like other great athletes, Novak has been pushing back against father time. Craig Boynton, elite coach

That retirement was the second time in barely six months that Djokovic, once a master of best-of-five tennis and seemingly bulletproof, was forced to withdraw from a major. In the French Open quarterfinals of 2024, the Serbian star suffered a torn medial meniscus (right knee) during his fourth-round win over Francisco Cerundelo. He was then forced to issue a walkover to Casper Ruud.

“The question Novak is probably asking himself, or I would be asking if I were his coach would be: ‘Okay. How do I get seven matches at a major at this level?’” Paul Annacone, the Tennis Channel analyst told me in November. “Can I still do that? Can my body handle that?"

It’s a critical question, and one Djokovic may not be able to regard with an objective eye. “Novak is in a part of his career where he's playing for his legacy,” Boynton said “When you're in the midst of that, you feel like you can do it. Like other great athletes, Novak has been pushing back against father time.”

The danger for Djokovic is that if he pushes back against the clock too hard, he may jeopardize his longevity and the long, graceful exit he seeks. Djokovic is, as Annacone put it, “A guy that really empties the bucket in terms of using science to figure out how to maximize his fitness and stuff.” But the toll exacted by those long Grand Slam matches is undeniable, and a challenge even to the young bucks.

By the same token, Djokovic has every right to feel that he’s still in the thick of it. His record indicates that he is just one upset, one slip by a rival, one stroke of providence removed from Grand Slam title No. 25. His calculations must accommodate the fact that if he wants to stay in the hunt, keep up his ranking, earn seedings, and remain sharp for 2026 and beyond, he will need to compete and win. The capital represented by rankings points does not generate interest.

Djokovic played just 13 tournaments in 2025 (Félix Auger-Aliassime, who is ranked just one spot below Djokovic, played 25). If he chooses a similar path in 2026 he will again have a very slim margin for error. Arias would like to see Djokovic play at least one tune-up event before every major.

‘It's difficult to not play a match and then go straight into three out of five sets at his age and think you're going to last for seven matches,” Arias said. “I do think those other two guys are now better than him. If Djokovic does last until late in a tournament, his own body may be breaking down. We don't even get to see him at his absolute best against them.”

Ironically, Djokovic might stand a better chance of stopping either man if they met earlier in a tournament, when he is fresher. But his high seeding has ruled that out—at least for now.

Of course, I’ve thought about [retirement] a few times, but in the end, I decided to simply play my way—to play where I want to play, not where others think I should. Novak Djokovic

Annacone believes that the Australian Open is the ideal target for Djokovic. Djokovic holds the record in Melbourne with 10 singles titles. More importantly, he’s had plenty of time to prepare and, like everyone else, he will go in fresh. Roland Garros and the level of fitness its surface demands will be a major challenge, and even a good performance there could adversely impact Djokovic’s chances at the tournament where Annacone and others believe that Djokovic has his best shot at winning, Wimbledon.

A reduced schedule offering plenty of down time can help a player’s fitness, but Boynton has seen that as keen as an aging player may be to train, there’s a limit on how many consecutive days he can go hard. “You might show up at a tournament ready, tennis-wise,” he said, “but energy-wise and recovery-wise, you're behind the eight ball, already at a deficit. So it becomes a balancing act.”

Smaller, less exhausting, best-of-three ATP 250 or 500 events could become Djokovic’s career-elongating safety valve, should the rigors of Grand Slam events finally prove too brutal. He will be free to play anywhere he wants with a wild card and tread water until the LA Olympics.

“Personally, I understand people’s curiosity,” Djokovic said in Athens, as speculation about his retirement mounted—only to be snuffed out by his announcement about competing in the next Olympics. “Of course, I’ve thought about it [retirement] a few times, but in the end, I decided to simply play my way—to play where I want to play, not where others think I should.”

Fitting words, from an icon who has made doing things his way the guiding principle of his life.