Novak Djokovic described his recent five‑set, nearly five‑hour battle at the US Open as something he "despised" every minute of, and the loss has reignited speculation about whether the Serbian legend should call time on his illustrious career. The 24‑time Grand Slam champion suffered an unexpected first‑round defeat at Flushing Meadows, falling to Argentina’s Mariano Navone – a result that marked the first time Djokovic has been eliminated at the opening stage of the US Open. Prior to this match, he boasted a perfect 19‑0 record in US Open first‑round encounters and had not lost his opening match at any major since Paul Goldstein upset him at the Australian Open in 2006. The 39‑year‑old was visibly exhausted on court, battling recurring nausea, frequent bouts of pain, and a general sense of physical depletion.

At one point he fought back tears, yet managed to smile graciously as he congratulated world No. 49 Navone on what is undoubtedly the biggest victory of the Argentine’s career.

Djokovic also confirmed that the underlying health problem he disclosed two weeks earlier is "serious," though he remains determined to address it and return to form. Djokovic has previously hinted that his ultimate farewell could come at the 2028 Los Angeles Olympics, where he would once again wave the Serbian flag for a final time.

In the meantime, former Wimbledon champion Marion Bartoli called the spectacle "heart‑breaking," noting how painful it was to watch the multiple‑time champion suffer so visibly. "The way he was physically suffering is worrying.

His health should come first, so he needs to have proper medical checks to see what happens," Bartoli added. Former British No.

1 Tim Henman also weighed in, describing the match as "a tough watch" but stopping short of advocating retirement. Henman praised Djokovic’s effort, pointing out that the Serbian was still fighting for every point despite feeling ill and even vomiting on court. "When he was up two sets to one with a break in the fourth, you thought he could," Henman recalled, emphasizing the resilience that still defines Djokovic’s game. However, he also cautioned that at 39, the physical toll is undeniable.

"His mentality and will to win are still good enough to win titles, but the physical challenges of being 39 and what his body is going through are tough," Henman said. "When you hear him saying he ‘despised being out there,’ that’s awful.

I’m sure he will go away and assess things because that’s not the way we want to see Djokovic depart any tournament." American player Ryan Harrison echoed the sentiment, noting that Djokovic has been wrestling with his body for weeks, a struggle that also saw him bow out in the first round of the Cincinnati Open earlier in the month. "It’s frustrating whenever you’re battling your body a little bit, but not enjoying the moment that you’re in specifically because it’s difficult is quite different from not enjoying the entirety of the sport," Harrison explained.

He added that Djokovic is likely looking toward a comeback in 2027 and remains, in his view, "a great player and still at the top of the game." The broader tennis community is now debating whether this painful episode signals the twilight of Djokovic’s era or simply a temporary setback. On one hand, his record of 24 Grand Slam titles and a career spanning two decades sets a high bar for any potential successor.

On the other hand, the combination of age‑related wear and a newly disclosed health issue raises legitimate concerns about his longevity at the elite level. If Djokovic does choose to retire at the 2028 Olympics, it would be a fitting bookend to a career that has seen him dominate every major tournament, often in dramatic fashion. Yet many former players, including Henman, argue that retirement is a personal decision and that the sport would suffer if the world’s No. 5 simply walked away because of a single poor performance.

In the meantime, fans can continue to follow Djokovic’s journey through upcoming events, including the remainder of the US Open, which is being broadcast live on Sky Sports. The tournament will run through early September, offering ample opportunity for the Serbian star to reassess his health, seek specialist advice, and perhaps stage a resurgence later in the season. Whether he decides to push forward, take a sabbatical, or retire altogether, his impact on tennis is already cemented, and any decision he makes will be respected by a global audience that has watched him win, lose, and fight with unparalleled tenacity. As the conversation evolves, one thing remains clear: Novak Djokovic’s legacy is already secure, but the next chapter—whether it involves a triumphant return or a graceful exit—will be watched closely by fans, commentators, and fellow athletes alike.